The Talented Mr. Dogfish

Summary

Podcast Summary: The Dating Detectives

Episode: The Talented Mr. Dogfish

Date: July 20, 2026
Host: Dear Media
Guests: Mackenzie Fultz (Private Investigator), Hannah Anderson (Comedian), Emily Will (Guest/Storyteller)

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Episode Theme & Purpose

This episode dives deep into a harrowing real-life tale of betrayal, financial deceit, and romantic manipulation. Guest Emily Will bravely recounts her experience dating “Leo” – a man who turned out to be a master manipulator, conning her and others out of money with a web of elaborate lies, fake jobs, and double lives. Mackenzie and Hannah guide the discussion, highlighting red flags, unpacking the emotional impact, and offering support and insight to listeners navigating the treacherous world of modern dating.

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Key Discussion Points & Insights

1. Emily's Relationship Beginnings

• [03:38-06:20] Emily and Leo meet during the early pandemic in Chicago, bonding over shared interests, especially finance.
• They start a long-distance relationship after Emily returns to New York, and eventually Boston for a new job.
• Leo appears charming, successful, and attentive, quickly integrating into Emily’s friend group and life.

"He was funny, smart, checked a lot of the boxes I was looking for... we hit it off immediately." – Emily ([04:12])

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2. Building Trust and a Life Together

• [06:20-09:09] Despite the long distance, the relationship feels secure, healthy, and mature.
• Leo moves from Chicago to Boston to live with Emily, sharing rent proportional to their incomes. He appears financially stable and pays for most shared expenses.

"He always made me feel really secure about things. It felt like one of the healthiest relationships I had ever been in" – Emily ([07:50])

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3. Financial Shifts and Suspicion

• [09:09-15:07] Leo claims burnout from his high-pressure finance job and takes time off to "find himself," allegedly supported by savings. He provides account screenshots to assuage worries.
• Emily handles more joint expenses temporarily, expecting repayment once Leo’s new "hedge fund job" begins.

“He showed me some of his accounts to make me feel more comfortable... I cannot never work again, but I'm fine for a while...” – Emily ([10:50])

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4. The Unraveling: Red Flags and Discovery

• [19:05-21:29] Once Leo’s alleged job starts, repayment never materializes. He always has excuses — delays, “moving funds,” or promises once a signing bonus arrives.
• Leo CCs Emily on faux email threads with a “UBS wealth manager,” using believable, corporate-looking communication to deflect suspicion.
• During house and travel planning, Emily is fronting large sums of money on her cards, expecting payback.

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5. Emily Finds the Second Phone

• [21:29-25:13] While moving, Emily finds a working second phone in their closet. Upon unlocking it, she uncovers a trove of evidence: Leo is cheating with multiple women (often from “Seeking Arrangements”), sometimes bringing them to their shared apartment.

"I don't think I had ever known what shock actually was until that moment... realizing how much the person I have lived with... has been lying to my face every single day." – Emily ([22:17])

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6. Cheating and Deception Layers

• [25:13-28:47] Many women Leo contacts are being paid or expect payment; some are even left unpaid and upset. He openly references Emily in these exchanges, sometimes using her schedule to arrange trysts.
• Emily is overwhelmed and plans not to confront Leo immediately to maximize odds of recovering the money he owes her.

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7. The Airport Confrontation

• [30:08-34:40] Preparing for a trip to Hong Kong (which Emily paid for), they reach the airport. Leo “forgets” the tickets; Emily realizes it’s all a lie. In the car, she confronts him about the cheating and missing money.
• Leo stonewalls, offering no answers, simply going silent and staring straight ahead.

“He just stares at me and says nothing. And I'm like, you don't have tickets to Hong Kong, do you? And again, nothing.” – Emily ([31:35])

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8. Connecting with Other Victims

• [35:41-37:08] Emily reaches out to other women Leo deceived. Shockingly, he keeps up the scam with elaborate ruses, including a second phone persona (“assistant Amelie”), and owes these women money too.
• The scope of his deceit is broad, involving multiple women, fake identities, and elaborate plots.

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9. Leo’s Lies Unravel Further

• [39:01-42:17] Leo finally admits he never worked in finance or had an MBA, instead working at a philanthropic organization and masquerading about his job and education.
• He had no way to repay Emily, and the "wealth manager" was a fake email he’d created.

"I have no idea. I don't know. Because I did see his accounts at various points and it had money ... but the job that I found out that he had, there's no way that he could afford that." – Emily ([42:47])

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10. Aftermath: Financial Fallout and Emotional Healing

• [47:14-54:47] Emily is left with $60,000 in debts on her cards, unpaid moving expenses, and her credit in shambles. Leo continues to attempt contact but offers no restitution; his parents refuse involvement.
• Legal recourse is daunting and costly, and recovery is slow. The deception leaves lasting scars: trust issues, anxiety, PTSD-like symptoms, and difficulty making major decisions.

"There was a long period of me not feeling like I didn't want to make any kind of decision because I felt like I couldn't trust my own decision." – Emily ([64:30])

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Notable Quotes & Memorable Moments

• On Shock and Betrayal:
  “I don't think I had ever known what shock actually was until that moment.” – Emily ([22:17])
• On the extent of deceit:
  “Why did I pay to move our stuff twice? … And it's frustrating also all the things that I could have been doing this whole time had I not had this hanging over me.” – Emily ([66:14])
• On trust erosion:
  “He was all the green flags … it takes one person for you to see how easily people can lie to your face.” – Mackenzie ([54:05])
• On the healing process:
  “You can only do so much healing on your own, you need to have new experiences that reinforce that things are okay. You can have a healthy relationship and not everyone lies.” – Emily ([61:44])
• On emotional aftermath:
  “I want to say it was almost like PTSD. Like, even when I was working or just going about my day, I would see the messages in my head again and flinch...” – Emily ([63:15])
• On learning and moving forward:
  “That's the hardest part... the thing that helped me most to heal was to remain open and still careful...” – Emily ([62:15])

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Timestamps for Key Segments

• Meeting Leo & Relationship Foundation: [03:38–06:20]
• Life in Boston / Financial Arrangements: [09:09–10:42]
• Leo “quits” job and asks to borrow for new trips: [10:42–15:07]
• First suspicions & stalling on repayments: [19:05–21:29]
• Discovering the second phone and evidence of cheating: [21:29–25:13]
• Planned Hong Kong trip, airport confrontation: [30:08–34:40]
• Contact with other sugar babies: [35:41–37:08]
• Final admissions and discovery of career fraud: [39:01–42:17]
• Emily's financial and emotional recovery: [47:14–54:47]
• Trust issues and advice for listeners: [61:44–64:30]

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Host Commentary & Analysis

Red Flags and Takeaways

• The hosts reinforce that scammers often blend seamlessly in high-trust relationships.
• “Trust but verify” becomes a recurring theme, as even the closest partners can maintain elaborate deceptions.

“It takes one person for you to see how easily people can lie to your face.” – Mackenzie ([54:05])

On Healing and Moving Forward

• Both Emily and the hosts stress the importance of not letting betrayal close you off to future relationships.
• Openness, therapy, and support are crucial to regaining trust in others and oneself.
• Emily’s story serves as a cautionary tale for protecting financial and emotional boundaries, especially when someone asks for money under the cover of seemingly legitimate reasons.

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Listener Takeaways & Support

• Red flags don't always look like red flags at first. Even "perfect" partners may be hiding secrets.
• Kinks and alternative relationship arrangements require consent; deception and harm are never acceptable.
• Financial entanglement, especially when fronting or loaning significant sums, should be approached with extreme caution.
• If you've experienced similar deception, you're not alone—community and professional support are available.

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Final Reflections

Emily’s courage and transparency provide vital lessons on vigilance, self-protection, and resilience. The hosts, Mackenzie and Hannah, offer validation, empathy, and practical wisdom for anyone navigating trust after betrayal. Their mantra: trust, but verify — and don’t be ashamed to seek help.

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Connect with the Show

• Share your story: [e-mail]
• Social: @DatingDetectivesPodcast on TikTok, Instagram, Facebook, YouTube Shorts

Ending Message: “Trust your f*ntuition!”

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Transcript

[Hannah]

The following program contains names, places and events that have been anonymized or fictionalized for the purposes of protection and safety. The following program is provided for entertainment purposes only, and any commentary from the hosts are strictly conjecture and should not be held as making any definitive statements about the truth or identity of any particular individuals or circumstances. If you or a loved one are involved in an abusive relationship, please call the National Domestic violence hotline at 1-800-799-6-7233 for support. Happy dating, detectives. Happy dating.

[Mackenzie]

We love you guys so much.

[Hannah]

We just had the best time in Chicago. Thank you for everybody that came to our live show. Oh, I'm reeling.

[Emily Will]

I'm on a high.

[Mackenzie]

Last week was insane, amazing. And let me just say, as always, I want to express my gratitude, but man, you guys really showed so much love and support. Thank you, thank you, thank you, thank you. Thank you for supporting our show and listening. Thank you to our Patreon and just all of our sleuthies and for listening to the show. Coming to the. The live show. And we just were obsessed with you. The next live shows are going to be in Orlando August 5th and Tampa August 6th. So if it's anything like the Chicago show, we're like, ah, going to be amazing.

[Hannah]

The tickets are selling and they're linked below, so go get your tickets if you're in Florida. And also adding to your gratitude. Thank you for sharing stories with us that y' all see online. Our guest today, Emily Will. I'll tell you more about her in a little bit, but she somebody, you know, you guys sent her tik tok to us and it's such a good story today. And also very. I know we say it every time, but like a very valuable story that important to hear.

[Mackenzie]

Well, it so is because the more we share these stories, the more we're using our voice as a weapon to fight back against these situations that happen that everybody, we don't. Nobody wants to talk about it because they're so ashamed. And so we really appreciate when you guys come on and so vulnerably share what happened to you so that we can again use our voices as a weapon. So just so courageous.

[Hannah]

So thank you for engaging with that conversation with other people and sharing the show. If you're in Patreon. Thank you, thank you, thank you. We do $5 a month and you get two bonus episodes and all kinds of other stuff and access to stuff before everybody else or we just get to, like chat with you more in depth and then you get all of that plus ad free listening if you do the $9 a month. So thank you, Patreon. Thank you, live show. Get audience. Thank you, future live show audience. And thank you, listeners. Thank you, mackenzie. I'm like, I feel like I'm accepting an award. I want to thank the Academy.

[Mackenzie]

We're still reeling. We're just obsessed with you guys. Let's just be real. We're totally obsessed with you. So thank you so much. And yeah, I think this week's guest, you're really going to. I mean, I just. I don't understand how these folks.

[Hannah]

I don't understand. I know.

[Mackenzie]

I'm still confused, but let's give Emily the floor and just hold on to your seat. Hold on to your pants.

[Hannah]

I need everyone's reactions and commentators, these things.

[Mackenzie]

Yes. Thank you for being here, Emily. We're so glad to have you. I don't know how glad we are, but thank you for being here and sharing your story.

[Emily Will]

Thank you for having me.

[Hannah]

We're happy to meet you. We'll. We'll say that it's great to meet

[Emily Will]

you guys as well.

[Hannah]

Well, take it away. It's. You have the floor.

[Emily Will]

Okay, thank you. Yeah. So I met Leo during the pandemic, early 2020. I was actually visiting a friend in Chicago at the time and ended up quarantining with her because that's when the lockdown started. But just after that, I met Leo on a dating app and we agreed to meet up. It wasn't a big date or anything. We just went on his rooftop and had some drinks and a Covid date. A Covid date, exactly. Yes.

[Hannah]

What dating app? I always like to know hinge.

[Emily Will]

I was actually just getting out of another relationship at the time, but was excited to meet new people. Wasn't really expecting much to happen, but we hit it off immediately, had great conversation. He asked me a lot about myself and vice versa. He was a couple of years older than me, like four years older than me, but he was funny, smart, checked a lot of the boxes I was looking for in a boyfriend and was really fun to talk to. We talked a lot about travel and work and random interests. We both really liked reading and had a lot of commonalities that were easy to chat about.

[Hannah]

What did he do?

[Emily Will]

He told me that he worked in investment banking at a large bank. I was also going into finance at the time, so we bonded over that. But yeah, just seemed very nice, normal. No red flags immediately. So we kept in touch, saw each other a few more times while I was In Chicago for about two months quarantining. And then I eventually went back to New York, peak summer of 2020. And that's when we were deciding, okay, are we going to make it official and be exclusively boyfriend and girlfriend? That would mean a long distance relationship since he was still based in Chicago. So I remember talking to my friends when I first got back to New York about this guy, and I didn't know if I should immediately jump into this next relationship or stay single because I had just gotten out of another relationship. But then I was like, oh, no, this is a really great guy. Seems dumb to not date him just because, I don't know, I want to have fun in New York. I don't know.

[Mackenzie]

So I. Yeah, why not pursue it?

[Emily Will]

Yeah. So we agreed to do long distance. He came to New York, met a lot of my friends. I was actually moving apartments with one of my friends, and he came and helped us remove so much stuff, which I thought was so kind of him. All of my friends really liked him. He was really funny. And eventually made individual friendships with my friends as well.

[Hannah]

How often did you see each other?

[Emily Will]

I want to say maybe twice a month for about a week at a time. I stayed in New York the whole pandemic, pretty much. And his job was remote. So he would come to New York for a week, then go back to Chicago for a week and go back to New York. Or we spend like two weeks. Yeah, it was a lot. And then outside of that, we did some random road trips around New York and Connecticut and stuff together, which was nice. It was a really pleasant way to spend the pandemic, to be honest. And so we were dating for about a year. Then I got a job offer in Boston, summer of 2021.

[Mackenzie]

How far is that from New York? Boston from New York. How is that?

[Emily Will]

Like a four hour drive?

[Mackenzie]

A four hour drive. Okay.

[Emily Will]

So I moved up to Boston for work, and then we continued long distance. He was starting to go back into his job, having to not be fully remote. Sometimes he needed to be on site. So when I met him, he was in investment banking, but leaving that role and going into more of a financial consulting firm. And this is back when consultants would spend Monday through Thursday at their client's site and then go home for the weekend kind of thing. So he was doing a lot of travel on site to visit his clients for work, and then on the weekends he would come to Boston a lot instead of back to Chicago. So we just continued kind of long distance, but still saw each other very regularly.

[Mackenzie]

With the long distancing, was there any trust issues, any communication issues, or did it work out pretty well? There was no concern there.

[Hannah]

Good.

[Emily Will]

Yeah, not really any concern. I think I had some trust issues from my past relationship, but he always made me feel really secure about things. I didn't have. Have a reason to believe that he was doing anything that I didn't like. It felt like one of the healthiest relationships I had ever been in, which was super refreshing. And we didn't have a lot of disagreements or arguments or anything when we did. We had very healthy styles of communication to kind of work through them. So it was really great. And as mentioned, he was a couple of years older than me, so I was like, wow. Maybe it's because he's had more relationships and he's more mature and, like, he just gets it. I don't know. Whatever. We'll get into that later. But, oh, boy.

[Hannah]

I know we're, like, gassing him up right now. I'm like, why are you.

[Mackenzie]

This is amazing. This is wonderful.

[Hannah]

This is not.

[Emily Will]

Which just makes it that much more concerning. But anyway, so we continue long distance, do some trips together and stuff. He continues to meet my friends. I've met some of his friends, his family. And then it's time for me to renew my lease in Boston, but now we're talking about getting a place together. So I end up staying in the same building, but I get a larger apartment and we decide to share the rent. He applies to the lease and everything. Everything goes well.

[Mackenzie]

Oh, nice apartment.

[Emily Will]

Yeah, it was great. He gave up his apartment in Chicago and moved his stuff to Boston, but it was great he moved in. And it was nice to know that even though he was still traveling a lot for work, now every time he would come back to Boston instead of, like, sometimes you were. Yeah, exactly. So, yeah, that was exciting. He made more money than me, which was not a surprise to me because he was older. So we agreed to share rent proportionate to our incomes. And, yeah, that was super comfortable for me. And throughout our entire relationship, he always paid for dinners and drinks, and most of our trips and things like that I would pay for, like his birthday dinner, get him something. But for the most part, he was paying for everything that we did. So we were in Boston. And then about six months into our lease, he was talking about how he was really burnt out with his job, wanted to go to a different company or not have to travel so frequently, just do something else, which I understood. I could see how stressed he had been doing all the Travel all the time. And I think a lot of people in finance hit a point where they're like, okay, I want to pivot into something not as intense.

[Mackenzie]

Yeah, yeah.

[Emily Will]

So that was not really a surprise for me. He decided to take some time off of his job to apply to other things and just kind of figure it out. And we talked about what that would mean for our finances, like him contributing to rent and everything. And so that's when we had a big discussion about finances and how long he could actually not work before it becomes a concern.

[Hannah]

What else came up in the finance discussion? Was that like, a full disclosure or kind of just what we need to talk about because of rent?

[Emily Will]

Sort of. He showed me some of his accounts to make me feel more comfortable that he's like, I cannot never work again, but I'm fine for a while, and we can continue life as usual. So I was like, okay, yeah, as long as you're not messing up my rent situation, like, we're fine.

[Hannah]

That was like, you weren't combining anything or.

[Emily Will]

Yeah, exactly. So he left his job December 2022, slash January 2023, that he, like, left his job and started applying to other things. And so he started the interview process for this hedge fund that was based in New York. Not a surprise. It seemed like a normal trajectory for someone of his experience. And so started the interview process. I remember him spending a whole weekend working on this case study, locked in our. Working on it. We would talk about it a little bit, and then he was going through the interview process. I could hear him on these interview calls. I remember the final interview that he was doing. I was in the living room, basically. I could see the back of his computer, but then his. He was facing me. Yeah, exactly. And the call was an hour and a half long, but I was just sitting there and pretending not to completely eavesdrop. But also I was excited. So I was like, of course, kind of trying to, like, keep him up, basically.

[Hannah]

Was he wearing headphones?

[Emily Will]

Yeah, he was wearing headphones, but he was talking through one of the case studies that he had been working on. And then a week later, he got the job offer. And we were very excited, went out for drinks to celebrate. But the job didn't start until this was, I want to say, like, April, maybe, of 2023. And his job didn't start until June or July.

[Mackenzie]

So how long was he out of work by that time?

[Emily Will]

Three or four months or so before he got the job offer. So around that April time, we were starting to plan our summer travel. And we had gotten a house in the Hamptons in prior years and just like, rented for like a month or so. And we would have friends come. So we were looking at houses to rent or thinking maybe we'll go to Europe for two weeks or something. So we were kind of, like, looking around at all of these plans of what we would do. And then he was like, would it be okay if you book these things and then I'll repay you when I start my job? And part of it was kind of like. It was in the phase. I was doing some travel for work, and I loved being able to get the points for stuff that I didn't have to pay for. So I said. I was like, yeah, we can put it on my. I'll get 5x the points or whatever. Let's do it. And I felt comfortable with it because I had seen the job offer. We had been together for over two years. I trusted him. Nothing had ever really been that much of a red flag, so.

[Hannah]

And he's paid for everything up until this point. Not everything, but, like, most things.

[Emily Will]

Most things, yeah. So I was, like, happy, happy to help. And so I did. I booked our Hamptons house, and one of my friends was actually going to stay with us for most of that month. So he sent me some money for a room in the house, too, but I fronted the whole cost, basically. And then we had booked a week in Europe. He had sent me the hotel. He had my credit card, and so I would just give it to him. He would book it, and then I would just see the charge, and I don't know, it was fine. But I wasn't part of making the reservations or anything because I was still working, he wasn't working. And I was like, that's your job for right now. It will be the travel planner.

[Mackenzie]

What was he doing when he wasn't working? What was he doing with his day?

[Emily Will]

He was working out a lot. I don't really know, actually. I was going to the office a lot. So I don't really know what he

[Mackenzie]

was doing during the day, but he wasn't like. He wasn't at home, like, playing video games, like he was keeping himself busy kind of.

[Emily Will]

No. He would go grocery shopping. He got into cooking. He would do a lot of cooking for us, actually, which was nice.

[Mackenzie]

Oh, nice. Okay. So he was doing something.

[Hannah]

He was enjoying his sabbatical.

[Emily Will]

Exactly. Yeah. I was kind of jealous, honestly. I was like. I was like, I hope I can take a sabbatical at some point.

[Hannah]

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[Mackenzie]

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[Hannah]

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[Mackenzie]

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[Hannah]

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[Mackenzie]

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[Hannah]

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[Emily Will]

So while we were in the Hamptons, it was June, his job had started, so he was commuting into New York City to go to the office. We shared locations for years prior to that, but sometimes I would check in to see how long it would be for him to get home and stuff like that. And he was always where I assumed he would be, at their office. And then I started asking for, then I started asking for repayment for things. And there would always be an excuse for why he can't repay me right now. Or like, can we just wait till I get the signing bonus? It'll come in the first 30 days. So by the time that he had started his new job and I was talking about being repaid for everything, he was talking about how he just wanted to move some funds around and he would like cc me on email threads with a wealth manager at ubs. And I chimed in at one point about like, when can we expect X amount or whatever. And I would receive an email back from this email saying a specific date that the funds should be good to go. And I was like, okay, well this is a real person as verified by the company website and LinkedIn. The email address wasn't sketchy, it was very corporate.

[Mackenzie]

Yeah. Yeah.

[Emily Will]

And so I was like, okay. And his job was focused on the Asia Pacific region. So they invited him to go to their Hong Kong office. And again, a lot of companies let you book travel on your own card and reimburse it, or you can use a company card, but for people that want to get points, people prefer to book on their own card and then get reimbursed.

[Mackenzie]

Yeah, yeah.

[Emily Will]

And so he was like, did you want to book this and we can get the points? And like, oh, sure. I was going to go with him to.

[Hannah]

Oh, you were?

[Emily Will]

Okay, I was going to go with him. I had never been. I really want to go. And his hotel would be paid for by the company. I would just have to pay for my flight. So I'm like, yeah, sure, I can book the flights, whatever. And then he was out of town. I think he was in Chicago visiting his family. And so basically, while we had this house in the Hamptons, we were also moving out of our apartment in Boston and gonna put stuff in storage for the month before our apartment in New York. So we were moving out of Boston. I was organizing everything for the movers. And I found a second phone, like, in our closet.

[Mackenzie]

My butthole clenched. I was waiting for something to drop.

[Emily Will]

And at first, like, maybe it's just an old phone, whatever, but it wasn't dead. So I was like, okay. And I don't remember what the passcode was. Then I started, like, I was getting, like, really anxious. Like, I don't know. I had no idea.

[Hannah]

You liked. Your gut knew something was out.

[Emily Will]

Yeah. Like, my stomach dropped. And I tried a few passwords. I was literally shaking. And I got into the phone.

[Hannah]

You.

[Mackenzie]

You discovered the password? Just guessing. Yeah.

[Emily Will]

I don't remember what it was. I knew the password to his other phone. I never really looked through it, but I just knew it because I would change music while we're driving or something, whatever. And I started looking through it, and there were all of these texts with so many people that I didn't know. And it was very evident that he was cheating on me.

[Mackenzie]

It was women. Yeah.

[Emily Will]

And so many of them. And cheating on me in the worst ways. Like, when I'm at work, they would come to our apartment.

[Mackenzie]

Shut up.

[Emily Will]

For some reason, I almost felt like he wasn't even in the state. But I felt like I had such limited time to go through it, and I had to find everything. And then at a certain point, I was like, okay, no, I need to go through this deeply and figure out what's going on. And I started taking videos, and some of the things I saw were just so hurtful I was like, I can't even look at this anymore, but I just remember. I don't think I had ever known what shock actually was until that moment, because I was realizing how much the person I have lived with for the better part of a year has been lying to my face every single day. I found one where I was sick, and I had gone to bed early, and he had someone come over and they hooked up in the stairwell of our building. I was like, what? While I was. I was like, you would agree.

[Mackenzie]

Audacity.

[Hannah]

Oh, that doesn't sound fun. Okay, when did this start? Does you do. Does it go all the way back?

[Emily Will]

Back to. I found all the way back to, like, 2020. This was 2023. So back to, like, 2022. But I'm sure that it had gone on longer than that. He just wasn't living with me before then. And things that I saw on the phone didn't really align with him being at his job five days a week, as per. I thought, like, he would see girls in New York while I would assume he was at his office. And I'm like, surely you can't just leave your new job in the middle.

[Mackenzie]

Yeah, like, what are you doing? I'm taking an extended lunch break today.

[Hannah]

I'm like, maybe he's like, paid for a we work and just invited them over. And that's his office. Like, I'm imagining.

[Emily Will]

So strange. But I also knew the company. I knew the office. I had picked him up from that office building before. And so part of me was like, do you even really have this job? But then I was like, that's crazy. We're going to Hong Kong next week. That's crazy.

[Hannah]

To the extent that you're comfortable, can you share anything else that stood out to you that you saw in that moment?

[Emily Will]

So I noticed that a lot of them he had met on Seeking, or I guess it was Seeking Arrangements at the time, which is a site that connects women and men and, like, in relationships.

[Mackenzie]

Right? Ain't it? Or no.

[Emily Will]

Yeah, in relationships. But usually when there's a man or woman that has a lot of money and someone else is like, oh, like sugar daddy stuff. Yes, very much so. Like a sugar daddy dating site. So I would see, hey, this is blah blah from Seeking or whatever. So then I went to Safari and I went on Seeking and all of his history came up, and it was just like, seeking, seeking, seeking, seeking, seeking. All linked to his profile, and it was the saved login. So I logged in, I saw his profile, I saw his messages with other people. And I was like, what?

[Hannah]

So he's paying all of these people?

[Emily Will]

Yes, but not all of them. Because also in the text, I see girls that are like, this check didn't clear. You owe me money. Like, all this stuff. But then I also saw on Apple Pay, there was like, minus 500, minus 1,000 minus. So, like, he was paying some people. He had booked trips for other people to hotels or flights or whatever. Flights, yeah. He had flown people into Boston and would get them a hotel. There were messages talking about me, which was disturbing.

[Mackenzie]

What'd he say about you?

[Emily Will]

Just that I would be at work or, like, I'm out of town on a certain weekend or when I was sick. He was like, oh, yeah, she went to bed early.

[Mackenzie]

Like, so he was not hiding that he was in a relationship.

[Emily Will]

Yeah.

[Hannah]

No, that makes me sad. That makes me really sad just thinking about the people that are like, whatever.

[Emily Will]

And what was really disturbing also is it almost seemed like some people had a cheating kink. Like, it was like they got off

[Mackenzie]

on the fact that relationship.

[Emily Will]

Yeah, yeah. Was adding to the whole experience, which I was like, I don't know. To each their own, I guess. So I was like, you're nicer than me. I was in shock. I couldn't even believe he was out of town. But I called one of my friends and I was like, leo is cheating on me. And she was like, what? How do you know? And I told her, like, all the stuff that I found. Yeah, pretty much like, all the stuff that I found on the second phone. And she was like, oh, my God, what are you. You gonna do? And we decided eventually I wasn't going to tell him yet. So when I decided not to bring it up to him immediately, it was really hard. And I had so much rage inside me that I wanted to just scream at him, honestly. But there was so much going on in terms of. I didn't know where I was going to live after this house ended. I. I didn't know really how to approach the conversation without him continuing to lie to me. And there's just no headway you can make in a conversation if someone's not going to admit the truth. I also knew how much money he owed me, and I really want to jeopardize that in case he did have the job and he could pay me back. Like, I didn't want to stir up so much drama that, like, he, like, almost like, when you find out, he's

[Mackenzie]

like, fine, I'm not paying you back.

[Emily Will]

Yeah, like, well, like, you invaded my privacy. So I just wanted things to remain status quo until I felt like I had my feet under me, and then I could handle that whole conversation, but I didn't know how it would go. I didn't know what the end result would be. And I felt like once I brought it up, I couldn't go back from it, because my immediate thought was, well, I'm paying for so much of our life right now. Are you using all of your money to pay them? Are you using my money to pay them? Why are you ripping so many of them off, too? Also, how long have you been cheating on me? All this stuff.

[Mackenzie]

So that's a lot.

[Emily Will]

It was a lot. And I was just kind of like, I. I really can't handle all of this right now. I just need to move. I need to figure out how to get out of this relationship. I did not sleep that night. I just kept looking through everything, and I didn't know what to do. Really?

[Mackenzie]

What do you do?

[Emily Will]

Yeah. I didn't want to immediately confront him about it because also, I'd seen how much he had lied to me just from the text, and I had no idea. So I'm like, surely he's not just gonna come clean, and I don't have it in me to have this whole fight right now. I'll do it.

[Hannah]

So did you talk to him? Did you have to text him? Good night. Love you?

[Emily Will]

Yeah, I just continued as normal. I didn't want to talk to him on the phone because I was like,

[Hannah]

yeah, I would sob.

[Emily Will]

Felt like I was gonna let it. Yeah, exactly. So the movers came. They packed everything up. They brought our stuff to storage. We went back to the Hamptons house.

[Hannah]

So you're, like, in person with him? I guess in my head, I thought he was maybe traveling. So you're with him, keeping it together as much as you can?

[Emily Will]

Yes.

[Mackenzie]

Wait, so he came home after you found it?

[Emily Will]

Yes. He was visiting Chicago while I was doing some packing, and then we met back up in New York kind of after that.

[Hannah]

How? What is that? Like, what is it like to see the love of your life and pretend like you don't know what they've been up to?

[Emily Will]

It was really difficult. I definitely took a lot more space than usual. Like, usually, I would be working from the living room or kitchen, and we'd be together, but instead, I would stay in the room and work. There was just so much of our life that was intertwined. Like, we hadn't signed a lease on an apartment in New York yet. So all of our stuff was in storage. We had this house in the Hamptons, but I didn't really know where I was going after that. And we also had that trip to Hong Kong coming up in the next week. And my plan for this was, I knew that I didn't want to have a normal vacation with this person, but I was like, once we get to Hong Kong, maybe I'll get my own room. I'll figure it out.

[Mackenzie]

Like, wait, you were still gonna go?

[Emily Will]

I was still gonna go. I still had my. Honestly, like, I kind of just wanted to go. And I figured I didn't know I

[Mackenzie]

dumped them before I dumped this asshole. He's taking me to Hong Kong or I'm taking.

[Hannah]

Yeah, you know, whatever.

[Emily Will]

Yeah. And at this point I was like, I'll probably still be refunded from the company. I'll get my own hotel room. He would be working for most of the day anyways. I'd be alone. And I just won't do dinners and stuff with him. I don't know. I was like, I can still have a nice time in Hong Kong, even if it's not a romantic trip. Whatever.

[Mackenzie]

Good for you. You're better than me.

[Emily Will]

Well, we'll see. But so it comes. We packed all of our stuff, we drive to JFK. We had a late night flight at like 10pm or something. So we park the car in parking, we take our bags on the shuttle, get to the terminal, and it's time to check in. And he was always really good with, like, he's very type A and I'm not. So he would handle all of our travel stuff. We get to the check in counter and the lady's asking for the tickets, and he's not doing anything. And I'm just looking at him and I'm like, where the tickets? Like, let's go. And he just stares at me and says nothing. And I'm like, you don't have tickets to Hong Kong, do you? And again, nothing. And I didn't know what to do. Like, I'm not gonna cause a scene in the airport. So we just grabbed our bags, got back on the shuttle, went back to the car, and I'm like, what the fuck?

[Hannah]

Wait, and you even. He had a flight that you were trying to make. Like, he knew the actual flight, he just did not have the tickets.

[Mackenzie]

Wait, didn't the money come off your credit card?

[Emily Will]

Yes, but to be honest, I wasn't looking that closely.

[Mackenzie]

Like, so where did the, where did the money go?

[Emily Will]

I don't know. I eventually did the full audit of my expenses during that time.

[Hannah]

Yeah.

[Emily Will]

And I don't really know, it just

[Mackenzie]

said like, American Airlines. And then it was like, just no tickets ever produced.

[Hannah]

Were produced from that.

[Emily Will]

Yes. My theory is maybe he bought points with it or used it for other flights with other girls or something.

[Mackenzie]

He used flights for them.

[Hannah]

That's the thing. It's like if you have a lot of flights on your statement, I get confused even in my emails sometimes and I don't travel a ton. It's like, which flight is which? And then especially it's not like it's saying like to Hong Kong on your credit card statement. So if you book.

[Emily Will]

Exactly.

[Hannah]

Another flight, you would see it.

[Emily Will]

That's what I thought. And so we get back to the car. He's silent. I was yelling for a second and then I was like, honestly, he was like in some kind of coma. So I was driving and then eventually we got back to the city and I was like, get out the car. He gets out of the car. And then I was having a complete breakdown and I drove upstate and got a hotel and just stayed there for like two days.

[Mackenzie]

So he had no answers? Like, he just said nothing. Like he was just.

[Emily Will]

There was no explanation. There was nothing. And so then I was upstate, but I still.

[Hannah]

I'm sorry, I need. I need a little more. So what are you exactly saying in the car?

[Mackenzie]

Like, are you just like, what the fuck? And he just says like, what?

[Emily Will]

What's happening? And then. And I brought up the cheating and I was like, I know that. Yeah. So like, that's huge. And he just said nothing. He just stared straight ahead and I

[Hannah]

was like, wait, can you tell us if you remember? Can you walk us through that? Like, what did you say?

[Emily Will]

So we were walking back. We were on the shuttles, getting back to the car and everything. And I was asking a bunch of questions. I was like, why didn't you book the flights? Are you ever going to Hong Kong? What is happening with this job? Do you even cover Asia? Do you even work there? And then I was like, how much are you lying about? I know that you're cheating on me. Like, how long is that? Like, nothing. But he was giving me nothing. He was kind of teary eyed and just not saying anything. And I. My blood was just boiling. I don't know. I didn't know what to do. I remember, Yeah, I remember he was walking to the driver's side and I was like, no, I'm driving. And he said nothing, just walked around to the passenger side.

[Hannah]

Got in and just got misty eyed. Oh, boohoo.

[Mackenzie]

Why would he let y' all get all the way to the airport, though? Like, he knew.

[Emily Will]

What did he think that they would, like, magically appear? Like, I have no.

[Hannah]

Did he think you bought them that?

[Emily Will]

No, I have no idea. Like, my theory is that he just is unable to tell the truth and he will take a lie literally, as I'm sure if we could have gotten to Hong Kong and waited outside of a hotel for a reservation that didn't exist, we would have done that too. So thankfully, that doesn't happen to me.

[Mackenzie]

He literally let you go all the way to the ticket counter before saying, oh, so there's my French.

[Emily Will]

It was so embarrassing. I was like, yeah, I was like, why are we standing here in front of this airport ticket counter?

[Hannah]

I just don't understand. I don't understand.

[Emily Will]

I don't understand. To this day, I don't understand. And this was like three years ago.

[Mackenzie]

So you got to the ticket counter, he's looking like a dumb. Like, what's going on? I don't know.

[Hannah]

He's looking like a cardboard cutout just staring at you.

[Emily Will]

His face, that is permanently burned into my brain. When we were at the airport and I was looking at him and he was just had this blank, almost guilty look on his face of like, I have. I've got nothing for us. And my blood was like, I had never been so mad in my life, honestly. So after the airport told him to get out of the car, and I drove upstate to crash out alone for a few days. And that's when I connected with one of the girls he was having an affair with. Just trying to piece more things together and get more information, probably to my own detriment.

[Hannah]

Oh, tell us, tell us, tell us what happened.

[Mackenzie]

How did you get a hold of

[Emily Will]

the sugar baby, turn her number on his phone? And he owed her money. She had flown to Boston multiple times. They had gone on other trips together.

[Hannah]

Did she know about you?

[Emily Will]

Yes. And her then he owed her money. But what was really crazy about that also is that the phone that I had, like, the second phone that I found, that number she associated with his assistant. And so she would have group chats with him and the phone number that I had for him and then this other phone, and he would pretend to be his own assistant named Amelie.

[Mackenzie]

What?

[Emily Will]

I was like, what?

[Hannah]

So weird.

[Emily Will]

So weird. I'm like, well, I guess that's what he was doing all day. When he wasn't working, he was making up a whole fake World with his assistant, Amelie, and coordination trips. And this girl is so confused. And I was like, this is the situation. This is him, his real number. He also is pretending to be his own assistant. And I am the girlfriend who has just found out about it. She asked me if I could help her in this situation, help her being stranded. And she was talking about how she feels really used from this whole thing, and he's not responding to her anymore, and she doesn't know what to do. And I'm like, girl, I can't. Like, I have nothing left in me right now.

[Hannah]

Just.

[Emily Will]

I'm sorry, but you gotta figure it out. I'm trying to figure it out, too.

[Hannah]

Do you know how much money he, I guess, helped her get out of New York. But do we know how much money she was owed?

[Emily Will]

I don't know exactly how much. I saw other messages with other girls where he owed one two thousand, one, five hundred, but I'm not exactly sure how those played out either. He owed me about 60,000 at the time. Dollars.

[Hannah]

Oh, my God, Emily, I'm so sorry that happened to you. This is, like, major financial dollars.

[Emily Will]

Yes, sadly. And so a day went by, and then we talked on the phone, and I was like, I really need to understand what's happening right now. Like, honestly, I feel like I blacked out for most of this conversation. And that's when he finally admitted that he didn't. He was like, yeah, I need to tell you that I actually don't work at SO and so. And I asked him, I was like, so, where were you going every day? I saw your location at their office. And he just kind of said, like, he would give me some things, but he didn't give me answers to everything. He didn't answer that question again. It was just silence. And I was like, are you ever going to tell me what is fully happening here? And he was like, well, what do you want to know? And then I asked him again, and he was silent again. And I was like, okay. Like, I don't understand. Okay.

[Mackenzie]

Okay.

[Hannah]

So what? Yeah. What did you get from him?

[Emily Will]

Just that he didn't have the job, he didn't have the money to repay me, and that he had cheated on me, but it's not what I think. And I'm like, what do you mean it's not what I think? I found this other phone, and he was like, oh, but that's from so long ago. And I was like, no, it's.

[Hannah]

You know, they have dates on text messages.

[Emily Will]

And when he admitted to not having this job. He did tell me what his job was, which was he worked at this philanthropic organization to help them raise money. This company was based in Cleveland, and I knew that for a while. While he was having his consulting job, he was doing a lot of work in Cleveland. I had gone with him at one point just to hang out for a few days, but come to find out his whole company there thought that he lived in Cleveland. But every time he would go, he would just pay for a hotel out of pocket to work there for the week.

[Mackenzie]

What?

[Hannah]

And this was when he was consulting, not when he got the hedge fund job?

[Emily Will]

This was the job. So he told me he worked in consulting, and that was the job he was burnt out of and wanted to quit. Come to find out, that job never existed. He was working for this other organization who thought he lived in Cleveland, but he was actually just paying probably like $6,000 a month to go to this hotel every week and pretend that he lived there, to work there Monday from

[Hannah]

Chicago through Friday, where he does have a home.

[Emily Will]

We were living in Boston together at the time.

[Mackenzie]

I'm.

[Emily Will]

So he was still going to Cleveland.

[Hannah]

Wait, so what did he. So he never had, when you met him, the job he had?

[Emily Will]

He had never worked in finance, basically.

[Hannah]

Oh, my God.

[Emily Will]

Yeah. Yeah, he never worked in finance. He also told me that he had gone to Northwestern to get his mba. Doesn't have an mba.

[Mackenzie]

Wow.

[Emily Will]

Never went to business school.

[Hannah]

Did anything ever come up when you were with his family where you'd say, like, oh, yeah, north.

[Mackenzie]

Look, there's a north detainer. Like, we're not really.

[Emily Will]

We never really discussed work when we were all together. And looking back on it, I'm like, how has that never really come up? But, like, every time we talked about work, it would just be super casual. How is work going up? Oh, it's good. It's stressful. Or like, I'm traveling a lot. I don't know. It's just very generic.

[Hannah]

Well, he might have been telling them that he had a finance job.

[Emily Will]

Yeah, I don't know exactly what he told them. I don't know exactly what he told his friends. I have no idea. And I also realized this wealth manager wasn't real. He was impersonating this wealth manager.

[Mackenzie]

How did he impersonate the email? How do you do?

[Emily Will]

Oh, my God.

[Hannah]

Yeah, get the email address.

[Emily Will]

Creating a fake email domain. And I have no. He did his research, though, because he was a real person, as verified by online sources. I was emailing with someone who had the UBS bank email address. And it was a real person. I saw them on the company website, but it wasn't him that I was speaking to. And then I wasn't actually speaking to

[Hannah]

him when he interviewed for the job.

[Emily Will]

Yeah, he was just like talking to someone or himself talking to himself for like hours on end. I don't know why he would dedicate an entire weekend to a case study that didn't exist. Or why you would commute four hours a day to get to Manhattan to go to a job you don't have. Just. That's a mind blowing.

[Mackenzie]

That's a lot to follow through with this lie.

[Emily Will]

Yes, agreed. Which is why every time I would have some kind of. Of anxious, I always just cracked it up to my anxiety. Because I was like, well, no one go this far to lie, but they do.

[Hannah]

So for three years he didn't ask for any money and he is acting like he has a finance job and is paying for everything. Where do we think he got that money?

[Emily Will]

I have another idea on the hook.

[Mackenzie]

Oh, my God.

[Emily Will]

I wondering, like, I'm like, was I the sugar baby to someone else's.

[Mackenzie]

Oh, my God.

[Emily Will]

I have no idea. I have no idea. Because I did see his accounts at various points and it had money and we did a lot of things together that cost money and I wasn't paying for them.

[Hannah]

So.

[Mackenzie]

So some. He had money at some point for something.

[Emily Will]

Yes. But the job that I found out that he had, there's no way that he could afford that off of what he was making. So I don't know.

[Mackenzie]

So it's a big fat mystery.

[Emily Will]

Yes.

[Hannah]

Oh, my gosh.

[Emily Will]

And then I also brought up, it seems like you owe a lot of other people money. He's like, that's all been sorted out. And I'm like, so did you cheat on me and pay them or did you cheat on me and never pay? Either way, like it is.

[Hannah]

If you're gonna cheat on me, at least pay them.

[Emily Will]

Right.

[Hannah]

You promised it. But then whose money are you paying them with?

[Emily Will]

Exactly? And I'm like, so why don't you have. Well, presumably you have no money to repay me because you've used it all on paying them or not paying them or, or whatever. And then eventually I was just like, I can't. I feel like I got the answers that I needed, which were he's lied to me about so many things and he can't repay me. And I was like, okay, I need to. I need to go. There's really nothing more to talk about. Like the cheating Honestly was, like, the least of my concern at this point. I was just like, I need to get an apartment. I need to, like, get all. You gotta figure out what you're gonna

[Mackenzie]

do for your life.

[Emily Will]

Yes, exactly.

[Mackenzie]

You guys, I have to tell you about my undies. My undies from Skims are amazing. So I lost £175 over the last couple years. And so my body is a little softer than maybe it was before. I've also had a baby. And what I love about Skims is I love their cotton fabrics because they don't squeeze the softness in my body so it doesn't make me feel like a busted can of biscuits. They are so comfortable and they feel really good on my skin. I love their bras. I love their undies. I love literally everything about them. The waistband, the fabric, all of it. I know. Hannah, you like skims too.

[Hannah]

I really do. I'm quite picky about undergarments and clothes in general. Like, if something's not comfortable, I am. I just can't. I really can't do it. Skims is truly the most comfortable underwear. And also, can I shout out there, they have a cotton jersey, straight leg pantry.

[Mackenzie]

Yes.

[Hannah]

I live in, like, change my standards for loungewear. Unbelievably soft, Stretchy, but not too stretchy. Somehow cozy, but also, like flattering. Like, they're just the best. Their pajamas are the best. But I. I know a lot of people who are very wide range of sizes and have a really hard time finding that perfect fit or also even color range.

[Mackenzie]

Yeah.

[Hannah]

And I like that Skims has both.

[Mackenzie]

Shop skims, cotton and all of our favorite [e-mail] after you place your order, be sure to let them know we sent you select podcast in the survey and be sure to select our show in the dropdown menu that follows. This episode is sponsored by Better Help. The stigma of mental health gets in the way of people actually getting the support that they need. Even though we talk more now about mental health than we have in the past, asking for help can still feel really hard. And actually, Better Help's latest research confirms that. BetterHelp's 2026 State of Stigma surveyed 2,000Americans and revealed that 85% of Americans believe that getting support is wise, but 74% say that society discourages people from doing so. Believing in mental health support and actually seeking it is something that we could really work to close the gap on. I know for me personally, I have a lot of anxiety and I suffer from all kinds of overwhelming thoughts, but sometimes things in just regular life feel really overwhelming. So I like Better Help because they give me the tools and resources that I need to help work through that. With over 30,000 therapists, better help is the world's largest online therapy platform. They've served over 6 million people globally. They have an average rating of 4.9 out of 5 for a live session, and they have a strict code of conduct and are fully licensed in the U.S. i really appreciate that they narrow down the therapist that they recommend based on the questionnaire that I fill out, and then I can switch my therapist at any time as it's comfortable for me. Don't let stigma stand in the way of support. Start therapy with Better Help. Sign up and get 10% [e-mail] TDD that's betterhelp.com TDD

[Emily Will]

then I remember I was staying with a friend for two weeks. Thankfully, I was a disaster. I would not have survived this period without my friends.

[Hannah]

And are you still working at this Boston job, or are you trying to get a new job in New York?

[Emily Will]

So I actually had just gotten a

[Hannah]

new job, of course, to make it easier.

[Emily Will]

Yes. I was fully remote, so I was going to be in New York, and I was just starting it, like, June of that year or something. It was like the last part of our time in the Hamptons. And then for most of July, I was staying with a friend, kind of figuring all this stuff out. I signed a lease in New York, and then I needed to get all of our stuff from storage. So I call the moving company, and I'm like, hey, I need you to deliver these items to New York. And they're like, well, we can't do that because we were actually never paid for moving you out of your Boston department. I'm like, what do you need? Because I specifically remember sending him money for the move. And I'm like, well, where did that go? So then I had to pay for the move again and then pay for everything to be moved to New York. And I was like, honestly, I'm just moving all of his stuff too. I'm just gonna take it and I'm gonna put it in storage and, like, sell this. Maybe I can get, like, some money back by, like, selling his bed, selling his couch, whatever. But he keeps calling me and texting me, and he's like, I need my stuff. And he's like, I don't know. I guess he also was trying to get some of his stuff back at this time. Like, I don't know how you were gonna get it. Back, but you also have to pay them again. But then he was, like, talking about him needing his stuff back, and I was like, I just consider this me buying you out. I just had to pay to move all of this stuff. Go figure it out.

[Hannah]

And none of his outreach is about trying to get back together, sort of.

[Emily Will]

He would text me and be like, we really need to talk all this stuff. And I'm like, no, there's really nothing more to talk about. He would call and FaceTime me all the time, and I wouldn't answer unless it was a specific logistical thing that I needed. But then he. And I don't know how he found out where I lived, but he would start showing up outside of my apartment. I remember I was coming home from lunch or something one day with my friend, and we see him sitting on the stoop of my apartment, and I'm like, what? What are you doing here? And we didn't go. We kept walking down the other street, and I was like, what is happening? What is happening? And then I finally went back and he was still there. And I wouldn't let him into the building. It was just a huge mess. And then he was in Chicago and he had to go to the hospital. For some reason, he was send me hospital photos. And he was like, I feel so terrible. I really just need to talk to you. And I'm like, I don't care. I don't care. For a second.

[Hannah]

I think he stubbed his toe and made a thing of it so he could send you sob story pictures.

[Emily Will]

It was insane.

[Hannah]

Like, is he telling any of your mutual friends anything about your breakup?

[Emily Will]

No. So I told. I mean, it was really embarrassing. So my closest, closest friends knew the details, and then I just told everyone else we broke up. I really, really appreciate it if you don't continue to update him on my life. And preferably you kind of cut ties. But I also had never been the person who was like, oh, we broke up and you can never speak to them again. But I was also like, this is a situation that I want everyone to be as far away from as possible at some point.

[Hannah]

It's like, if he did this to you, he would do this to someone else totally.

[Emily Will]

And then I also never reached out to his friends or anything. Eventually, months later, because my credit is now fucked, for lack of a better word, because I put all of this stuff on my card that I can't really afford on top of paying for my whole life. I remember actually I had gotten approved for an apartment, and I felt so Lucky because it was a week before I was about to get my next credit statement. It was right before my credit score took a pretty big hit because I wouldn't have paid back this amount of money. And I was like, thank God I got approved while I still had good credit. So eventually, a few months later, my friends were like, you need to reach out to his parents, ask them for money. So I worked up the nerve to send. I put him, his mom and his dad in a group chat and I just.

[Mackenzie]

And you had already met them by this point, right? Didn't you say you met them?

[Emily Will]

Yeah, we'd gone on vacation with them, but they didn't really say anything. They didn't reply to the message. And then separately he texted me and he was like, my parents aren't going to be responsible for the situation. I'm like, okay, whatever. I was kind of shocked. I mean, I guess as a parent I wouldn't want to take on responsibility for my kids mistakes.

[Mackenzie]

But also I'd feel bad for the person that he hurt.

[Emily Will]

Yeah. And I would probably wouldn't continue to support him. I knew that he was living with them. I don't know. I. I don't know.

[Hannah]

I feel like you go get a job and pay that girl back.

[Emily Will]

Right? Yeah, yeah. I don't know.

[Mackenzie]

It's not like dumb, like, it's not like he doesn't have the experience to get a job that pays well. Right. Like he educated, well educated dude. Like there's nothing stopping him. Yeah.

[Hannah]

He could be a model scout.

[Emily Will]

There you go.

[Hannah]

Goodness gracious. Okay, so you're not getting anything from him.

[Emily Will]

No. And I tried to look down the paths of suing him, but unfortunately I can't sue for legal expenses. And I've been advised depending on how long it drags out, it could rack up.

[Mackenzie]

It would cost you more money than anything.

[Emily Will]

Yeah, about as much as he owes me.

[Hannah]

Is there any con. I guess we've talked about this a little bit in previous episodes. So even though you consented to giving him this money, he didn't use it for what he said he was going

[Mackenzie]

to, which is a crime.

[Emily Will]

Yes. And we had very basic contracts or whatever, but I did want it in writing that I would be repaid.

[Hannah]

Oh my God. You had it in writing? And he was like, yeah, totally, no problem.

[Emily Will]

Yeah, yeah. So if anyone knows a pro bono attorney let me know. But yes, that's currently where we stand. I haven't been repaid.

[Hannah]

When did this, when was this?

[Emily Will]

2023.

[Mackenzie]

2023 in New York So you're looking for a pro bono attorney in New York who's willing to take this on and help you.

[Emily Will]

Chicago, I guess, because that's where he's based. I don't really know the jurisdiction that it would need to be in. I mean, it happened across Massachusetts, New York, and Illinois.

[Hannah]

So when you got into your new apartment, talk about trying to get back to yourself financially and emotionally.

[Emily Will]

Yeah, I definitely carried a lot of trust issues with me to every relationship, whether it was a friendship or dating,

[Mackenzie]

because you can't now. You're like, everybody's lying because I trusted him, and now everybody can just lie to me.

[Hannah]

He was all the green flags.

[Mackenzie]

You one. It takes one person for you to see how easily people can lie to your face.

[Emily Will]

Yes. And that's what was so shocking. I was like, I know people can lie, but I think the extent to which that he would take the lies, like going all the way to the airport, pretending to be in an office all day. Like, I don't. Was he just sharing locations from another device, or would he literally just sit outside of an office is for eight hours a day? I have no idea.

[Hannah]

Why do we. I mean, you said you're not. Obviously, I get wanting to cut ties, but do we see anything on social media, LinkedIn?

[Emily Will]

I have blocked him on everything. I would still get random texts and facetimes from him all the way up until. I didn't block him on text until summer of last year, and I would still get, like, random texts and facetimes that I never answered. I think part of me was just hoping that one day I'd get an Apple pay for like $10,000 if he'd start.

[Mackenzie]

Pay would be nice.

[Emily Will]

Yeah.

[Hannah]

What was he saying in these texts?

[Emily Will]

He would just be like, hi, or hey. Or I'd look at my phone and see a missed FaceTime call. And then I started dating someone else. Yeah, that's crazy. Crazy. I'm like, what do you even think I would respond to that? Like.

[Mackenzie]

Like, oh, hey, what's up?

[Hannah]

Good to see you.

[Emily Will]

Insane. I have no idea. So eventually I just blocked him completely, and I. I have no idea where he is or what he's doing in his life or anything.

[Mackenzie]

Was there any point after you found this out that you looked back and you were like, oh, my God. That was a red flag. Because hindsight's always 20 20, kind of.

[Emily Will]

I mean, there was one time where he was coming home from a work trip and I was at the office and I left the office early to surprise him and I thought we could spend the afternoon together and just hang out because we hadn't seen each other all week. And he was so angry at me for coming home and not telling him. But that was because he had just flown someone in, and he was planning to go meet them at the hotel, per the texts that I found.

[Mackenzie]

My God.

[Emily Will]

And I couldn't figure out, like, why he was so angry.

[Mackenzie]

Because you ruined his date with his sugar baby.

[Emily Will]

Yes. Yes.

[Hannah]

Oh, my gosh. And if you are gonna surprise him, he's like, how can I have girls over at random hours if I don't know when she's gonna come in?

[Mackenzie]

Yeah, how can I cheat if you're gonna come home early? That's stupid, Emily.

[Hannah]

How dare you?

[Emily Will]

I know. And then there was another time. Summer of 2021, I was on a work trip in New York, but we were going to the Hamptons with some friends. So he was going to meet us from Boston in the Hamptons, and I was going to travel there with my friends from the city. And he was running really late. He said that he had some issues at the bank that he had to take care of, and he ended up being, like, six hours late to the Hamptons. And I was like, what are you doing at the bank that takes so long to sort out? Out? And he was talking about how he had the margin call on his investments, meaning, like, borrow against his stock portfolio, but it dropped in the markets, and so his loan needed to be readjusted. Whatever. I was like, I don't know. I was like, this is not my problem, and I don't really want to think about it. And we weren't combining finances at the time. And I was like, that's your issue,

[Mackenzie]

but you're a finance girl. Did what he was saying make sense? Like, he, like.

[Emily Will]

You were like, oh, yeah, yeah, he definitely did. And a lot of my friends also work in finance. One of them worked at a competing hedge fund. And I remember them talking a lot about this new job that he was starting. He fit right in.

[Mackenzie]

Oh, my God.

[Hannah]

This is so bizarre. It's very, like, talented Mr. Ripley. He really fit the part, so he

[Mackenzie]

knew what he was talking about. Although he didn't go to school for it, he still knew a lot about finance.

[Emily Will]

Yes. Except for. I remember while we were dating, I was applying for other jobs and stuff, and a lot of what I needed to do for the interview processes were case studies and financial models. And I would ask him for help with things. And I remember sometimes he would talk with me through these Things and it wouldn't really make sense as to what I would do, but I just kind of trusted him because he had been working in banking far longer than I had, and I was like, oh, that must be correct. And so I kind of.

[Mackenzie]

And you trust this guy? Yeah.

[Emily Will]

Yeah. And so I don't even wanna think about how many jobs I didn't get just because I was like, oh, he must have been right.

[Mackenzie]

Oh, my God.

[Hannah]

Wait, that's crazy.

[Mackenzie]

That's insane.

[Hannah]

Oh, my God. Wow. So you're a couple years out and you did eventually wanna share on TikTok the story. So how's that been? What got you to that point?

[Emily Will]

For a while, I couldn't even talk about it without just feeling completely re. Traumatized again. I didn't wanna think about it. Even when I was looking into suing him. I couldn't really focus on it for more than 30 minutes without getting completely overwhelmed by this point. I've gone through other relationships that I felt were, like, somewhat healing. I've had a long time to process and I don't feel as ashamed of it anymore. Yeah, people in my life, it's so embarrassing. It's so embarrassing because everyone's gonna think, oh, that was stupid of you. But I'm like, honestly, I hope in the future still that two, three years into a relationship with someone and I trust them enough to. I don't know that well, that far

[Mackenzie]

into a relationship, that's a pretty good time. It's not like you're two weeks in and you're trusting him. This is someone that you've built a life with, like, what the hell?

[Emily Will]

Exactly. And people have brought up the point about AI now. Think about all of the other things he can face now because of this. And also, I don't know if he's still doing the same thing, trying to date other people.

[Mackenzie]

Of course he is.

[Emily Will]

And then also, the more that you talk about it, like, maybe I will find someone who can help me figure this situation out. Or like, I don't know. I'm just so tired of carrying, like, all of the consequences of this while he's probably gotten none.

[Mackenzie]

So he's just getting laid in stairwells. It's fine.

[Hannah]

Yeah, good for him. Anybody in the comments ever say, like, I think I know who this is?

[Emily Will]

Yes, some people have. I haven't, like, fully been able to verify it. Those groups on Facebook. Are we dating the same guy? I've thought about posting in there and I would really like to, like, I had honestly to, like, completely dissociate from it. Even when I was talking about it on TikTok. Like, I have an old whole album on my phone still of, like, all the screenshots and stuff that I found at the time. And I was going through it and the whole airport thing, I forgot that happened until I found messages of me talking about that. And I was like, oh, my God, I forgot about that. And I forgot about talking to this girl until I was going through it again. And I was like, wow, I really dissociated hard for, like, the last three years. Maybe that's why I'm okay now. Because even when I was going looking at stuff again, I was like, wow. Yeah, that was insane. I think I just spent so much time trying to make new memories and forget about him and forget that all of that happened, even though the financial piece still affects me. So that's the part that I remember most, but I think the multiple layers of the cheating and the lying and how far he took things and all of that, I tried to just kind of sweep under the rug to have any sort of healthy relationship with friends, family, other boys, like, because, I don't know, I just couldn't carry all of that with me. And, like, I think part of what helped my healing journey is trying to remember that this. While it's not like an isolated incident and people do lie and are insane, not everyone is like that. And just trying to remain open to. That's the hardest part.

[Mackenzie]

Yeah.

[Emily Will]

And if you can only do so much healing on your own, you need to have new experiences that reinforce that things are okay. You can have a healthy relationship and not everyone lies. And so I feel like I spent a lot of time isolating myself, but until I had more relationships with people that were healthier and they didn't lie to me and they didn't scam me out of money, it's really hard. And I feel like everyone, a lot of people, especially after I shared on TikTok, were like, commenting like, I would never be in a relationship again, blah, blah, blah.

[Mackenzie]

But you would have such a hard time. Yeah, yeah, yeah.

[Emily Will]

But it's so isolating. And the thing that helped me most to heal was to remain open and still careful and things.

[Mackenzie]

But that's so brave of you.

[Emily Will]

Be open to the new experiences because, like, you have to retrain yourself to know that this is.

[Mackenzie]

And also, what are the chances that something like that happens again?

[Emily Will]

Happens again. Yeah, exactly. I'm like, statistically, I don't think it will happen again.

[Hannah]

Hopefully.

[Emily Will]

Fingers crossed. Yeah.

[Hannah]

How has dating Been, if you want to tell.

[Emily Will]

Yeah, I. Well, you know, dating in New York is interesting in itself, but I've had situationships with people. I was in a relationship last year that was pretty healthy. We're not together anymore. But it had nothing to do with him.

[Hannah]

He had a job and it was his job.

[Emily Will]

Yes, that's another funny thing. He was also very kind of successful. More successful than most people his age. And I remember my friends were like, okay, well, we have to google him. We have to verify this. Like, we have to like, really dig

[Mackenzie]

into trust in all willy nilly.

[Hannah]

Trust, but verify.

[Emily Will]

Yes, exactly. So it's definitely been interesting. Like, I'm just. Yeah, it's just so humiliating and disgusting and violating and like, I was so uncomfortable in my own skin. And I even had like. Sometimes, like. I want to say it was almost like ptsd. Like, even when I was like working or just going about my day, I would see the messages in my head again and flinch because I'm like, oh. Like, I'd see. Just. I can't get it out of my head. And I had a visceral reaction to seeing these things. And I remember one time I was at brunch with my friends and I was like. And I flinched and I was like, no. And they were like, what? Are you okay? And I'm like, yeah, I'm just having flashbacks of all the stuff I saw on this phone. And that happened months, randomly.

[Mackenzie]

Wow.

[Emily Will]

It was exhausting. I was like, why am I having, like, PTSD from, like, text messages? But it was just truly so vile. Like, it impacted you so greatly. Yeah, I think it was also because, like, I trusted him so much.

[Mackenzie]

Like, but then it's like, you. You almost. I don't know if you're like most people. Most people feel like they blame theirselves because how did I not see it? Why did. How did. And then you feel stupid because now it's like I can't even trust myself to protect myself.

[Emily Will]

Yes, totally. There was a long period of me not feeling like I didn't want to make any kind of decision because I felt like I couldn't trust my own decision.

[Mackenzie]

Yeah, I'm stup. I can't make my own decisions. I made this big one and this was very bad. And now you can't trust yourself. And if you can't trust yourself, who can you trust? It's a spiral.

[Emily Will]

Yeah, it was really, really tough. And I think that's why I just tried so hard to forget about so many things because I didn't know how to really handle it. Yeah.

[Hannah]

Nor should you have to know how to handle that. You're definitely not an idiot. And thank you for telling us the story because you are a very good example of somebody who's not an idiot, who protected themselves, who's a hard working person. And it can happen to you, too, like it can happen to anyone. And it is very valuable to hear women like you share your story because you. You will make a lot of people feel less alone in theirs. So thank you for sharing on TikTok and then coming to talk to us.

[Emily Will]

Yeah, thank you for having me. Another comment I saw was like, I don't know, something about just, like, trusting people. But it's like, no matter, like, how much you look into something, like someone who has staked their whole life on a lie, like, they're lying for their life, they're always going to have a reason. They're always going to have an excuse. No matter how much you check, they will have something that checks out until you get to the airport and realize there's no flight. So.

[Hannah]

And that's why we go to therapy, y', all, because we just have to learn to accept the maybe of life.

[Mackenzie]

And.

[Hannah]

And that's tough.

[Emily Will]

That's tough to do.

[Hannah]

Let's do it together.

[Emily Will]

Yes.

[Mackenzie]

Oh, my God. That this guy. And it feels like there's no resolution. You still are out that money. You're still suffering the consequences of this.

[Emily Will]

And that's the most frustrating part. Now I feel I have healed mostly from the emotional part of it, but it's still tangibly impacting my life. Like, my credit.

[Mackenzie]

Your ruined credit is like a tangible sign. Yeah.

[Emily Will]

Yes. And I've had to pay for things that I didn't want to because, like, why did I pay to move our stuff twice? And it's frustrating also. All the things that I could have been doing this whole time had I not had this hanging over me. And also knowing that I don't know, like, I don't know what he's doing. He was, like, living with his parents, but, like, I assume he's gotten some kind of job in the last three years and he's probably now has a new apartment and continuing his life as if, like, he doesn't owe someone $60,000. So that's frustrating.

[Mackenzie]

Insane.

[Hannah]

I hope karma catches up.

[Emily Will]

Me too.

[Mackenzie]

That's insane. I can't. With this fella. I cannot, like, wait, wait, where. I want to know where he is. I want to know what he's doing.

[Emily Will]

Man.

[Hannah]

I am moving to New York And I have a lot of friends in New York and we joke about, like, oh, the finance bros. Red flag. But it's like, at least most of them are actually finance bros.

[Mackenzie]

I know, right? I can't believe that someone went to the length of. Well, first of all, why go so long? Just you spend all this time, like, not. Not doing anything that we know of, and then all of a sudden now you're a jackass and you're like, I don't get it. I don't. What was the I don't get this time? I don't understand any of it. I don't get it.

[Hannah]

Well, I can understand building a foundation with her. Like, I, you know, he. I think he could have feelings for her that are genuine in his way. I don't think they're like normal person feelings, but.

[Mackenzie]

And then.

[Hannah]

Right. And then you get security out of sharing an apartment with her, which is like, okay, he locked that down. He's got his home base. He can live his high life now. Like, I understand the motivation as much as it is abysmal. But then. Yeah, I think you were onto something when you said maybe he realized she found out because why else would it just blow up randomly? Why else would he just stand there at that, that airport counter.

[Mackenzie]

Yeah. And say nothing? He was frozen. It was like he was frozen in fear. And I feel like, like there was no indication based on her story that she was going to be some kind of cash cow. Like.

[Hannah]

Right.

[Mackenzie]

I just, I don't understand where he thought she was going to. It was like, all of a sudden he just said, hey, can you put this on your credit? And little by little, just started using her credit. And I don't think she had a bunch of cash. Like, I.

[Hannah]

No, she didn't have 60k in cash.

[Mackenzie]

Of course. I think she was using her. Her credit and ruining her credit, shall we say?

[Hannah]

It was a good warning sign to me because I am the person that's like, oh, put it on my card. I want the points.

[Mackenzie]

I want points.

[Hannah]

And I've gotten more into that recently. And not that it's a bad thing, but I just gotta remember, you know, you're in your third card when you cannot pay back.

[Emily Will]

As you become a grown up, you

[Mackenzie]

start to see that the points are actually so much fun.

[Hannah]

They're so fun. However, they're too fun when you can't actually pay the credit card back. And I think it's the same thing. You know, we always say, don't loan anybody money if you can't Live without it coming back.

[Mackenzie]

Just be ready to give it to you.

[Hannah]

Let's think of credit cards the same way.

[Mackenzie]

Yeah.

[Hannah]

It's a good reminder.

[Mackenzie]

I feel like a little bit of. I don't want to speak for Emily, but it seems like she was in shock. Like, she couldn't confront it right away just because of the sheer shock of everything. Isn't that what it seems like to you? Like, you find this out, but there's been no red flags or any indication whatsoever that this person is a skeezeball. And all of a sudden, sudden it slaps you in the face. Besides the fact that she hadn't been feeling very great, she was feeling. It was manifesting physically, but other than that, she didn't have any indication that this guy was a jerk face.

[Hannah]

And I've been there in my way. I haven't been there, and I'm very grateful for that. But where you have so many other areas of your life that could be the source of your anxiety, so it's very easy to write off.

[Mackenzie]

So how do you say, like, oh, this is him for sure. Like, you don't.

[Hannah]

She's like, I just got a new job. I moved. Moving. Of course I'm anxious.

[Mackenzie]

Yeah.

[Hannah]

Also, I'm glad the like she described blocking those memories, disassociating afterwards, almost blacking out in some of those conversations.

[Mackenzie]

Yes.

[Hannah]

And I know it's hard to understand. I have never experienced that. So we have to acknowledge that and just be like, I don't. I cannot speak to what she went through. And I also can't deny it at all because I think everyone handles it differently. Some people are like. Like, you know, fight or flight or freeze. And some people are fight. Some people are flight. Some people are free. Some people are a different one on a different day. And it's not anybody's fault the way they respond. We're not wired to respond to this.

[Mackenzie]

Well, yeah. And it's a. To. To forget or not to remember, whatever is. It's a. It's a trauma response. And I just, for example, I have. Have a little bit of a traumatic childhood, and I don't remember much of it. And so I'm learning more about it as I get. And my brain is allowing me to process those thoughts through therapy and everything. But I have totally disassociated from my childhood because of how traumatic it was for me. And I can only imagine someone like her going through this. And I'm sure she was thinking about a future with this person. Like, you're thinking of your whole life, and then all of a sudden, it's ripped out from under you. I could totally see why she disassociated from it.

[Hannah]

Oh, my God. And then I'm glad you, like, used the. Or she. One of you said it seemed like they had, like, cheating kink.

[Emily Will]

Kink.

[Mackenzie]

Yeah, that's what she said that they had. And I think that's a real thing too.

[Hannah]

Okay, so we are obviously sex positive here at the Dating Detectives, and we are not kink shaming. But I will happily kink shame if your kink hurts people.

[Mackenzie]

Yeah.

[Hannah]

Like that is the line.

[Mackenzie]

Because there's no consent. So kink is a thing. Right. But it's safe, sane, and consensual. When we talk about BDSM or kink or anything like that, the. The rule is, is safe, safe, sane, and consensual. But this person was. She was not consenting. So that takes away that part of the triangle that you need to have a vic. Like, that takes. That takes that away.

[Hannah]

I would also argue the sane part is not there. But I guess that's just me, right?

[Emily Will]

No, it's true.

[Mackenzie]

And so you take away safe, sane, and consensual, and you no longer have a kink. Now you're just cheating. Like, it's not okay.

[Hannah]

I've been thinking a lot about our episode with other Emily.

[Mackenzie]

Yeah. Last week and the week before. Yeah.

[Hannah]

We got a lot of Emily's. But how we talked about the way that her parent and then her dogfish was able to shape her experience because she was so young and groomed that experience. So say like, oh, this. What is abuse? I can define as love to you.

[Mackenzie]

Yes.

[Hannah]

And I. I think sex is very much that way for young people.

[Mackenzie]

Sure.

[Hannah]

Where the first experience you have could be with someone older that tells you, oh, you're shaming me if you're saying my cheating kink is bad. You know what I mean? So it's like, even though it seems kind of obvious at times, I think it's important to talk about how. Yeah. Anybody that's doing anything safe, staying consensual.

[Mackenzie]

Yeah.

[Hannah]

And I love how she talked about healing open to.

[Emily Will]

Yeah, yeah.

[Hannah]

Healing happened when she. She maintain openness and kindness and desire to connect, trust, but verify. Google the crap out of every single person. And I don't even care if their LinkedIn is right now. I. At this point, I. I imagine her going on a date and being like, if we're not going to your company holiday party, and I'm face to face with all of your co workers. We're not doing it. Like, I would be in the office delivering lunch, but good for her, because

[Mackenzie]

I was thinking the whole time, I'm like, man, I wish I was like her. Because if you hurt me, I'm gonna be closed off. Like, I'm like, well, I don't trust nobody ever again. Never. Just don't, don't. And I, to this day, I refuse. Like, I don't trust nothing to nobody. And I'm 42 years old who's had some experiences, and I refuse. But she's very, she's very adamant about keeping her heart and her mind open and there's something to be good for. That's, that deserves an applause because it's not. What are the chances that it happens again? Which it could, obviously, but she's saying, no, I really still believe in this. And I think that's incredible.

[Hannah]

I love how you talked about how her trust in herself eroded after, and she validated that, saying how hard it was to make big decisions afterwards.

[Mackenzie]

Well, because if you can't even trust yourself, what a shitty feeling that is to know that you like she. Okay, so this guy ruined her trust, right? Sure. It's his fault. It's not her fault fault, but she thinks in her head now, she, now her head is like, God, I can't even trust myself to make these decisions. That's a horrible place to be in. And you're like, I can't even live my life. I can't even trust myself. That is a shitty feeling. I, I, I get it. And I think a lot of us have been there, and that's where that stupidity, that feeling of stupidity comes in. Like, how could we let ourselves feel that way? And of course, it's never our fault, but we do feel like that we take the blame and it can hold us back. So the fact that she's just willing to stay open is just so incredible. I think it's something to learn from for sure.

[Hannah]

Absolutely. I mean, there's, this is a tough one she did. Not to say that. We never want to make it seem like, oh, she did everything right. So, like, it's not that anybody in the past has ever done anything wrong. It's just that this guy really showed no signs. Unless I'm curious if anybody's been in a similar situation. I hope not. But are there parallels to your experience, behavior that you recognized before all hell broke loose that you've seen before that we can learn from? I mean, I hate having to. But if you have had somebody that's been taking your credit card and spending it on seeking arrangements or similar financial fraud. Sugar baby. And just the funny. It's so funny how many sugar daddies are probably. It just deadbeat.

[Mackenzie]

Yeah. And to be fair, to be fair, nobody's kink shaming the whole sugar baby. Sugar daddy. I don't shame sex work like sex work is. Nobody's shaming. I don't. Whatever.

[Emily Will]

I don't.

[Hannah]

What do you say? Safe, sane and consensual.

[Mackenzie]

Well, it has to be legal, too. But that's. That's not. But you know what I mean. Like, I. I don't. I'm not going to shame anybody for it. Like, that's your life. Do whatever you got to do. Sex work is work. I don't care. But there's. There's a line that you draw when it's like, hurt people. Yeah.

[Hannah]

You. You're.

[Mackenzie]

You know about this other person and you're not. How safe is this? How safe Is this with STDs? How safe is this with maybe a physical position that now she's going to be in? What liabilities do we have if she finds out and she confronts him? Is he going to get violent? Like, there's way too many. There's way too much liability. It's scary.

[Hannah]

It's so scary.

[Mackenzie]

But nobody thinks about that. We.

[Hannah]

We will pass on any messages to Emily if you have experienced something or if her story spoke to you or you just want to send support. There's a comment section on Spotify. I know wherever you're listening. Might have one. But we're always on social media at Dating Detectives Podcast, TikTok, Instagram, Facebook, YouTube shorts. We've been posting more YouTube shorts. Thank you very much. I love that. I've been doing that.

[Mackenzie]

And. And if you have a story that you want to share with us, please be patient as we read them because we do get a lot of. But we welcome your story. We would love to be an ear or a platform for you. Our email address is Investigate the dating detectives podcast.com and again, thank you so much for an incredible show in Chicago. We cannot wait to see all of you who are coming to Orlando and Tampa. I know there's going to be a couple that come to every single show because we have some die hards and you guys are insane. And we love you.

[Hannah]

We love you. And if you have a story in Orlando or Tampa and you're like down to come on stage and share it with us, yes. You can send us an email at that address. As well.

[Emily Will]

Yay.

[Hannah]

Let's chat. If you've ever, like, needed to hear us in person, be like, what? That's crazy. It's not your fault. Like, this is your chance.

[Mackenzie]

And thanks again to Emily. We will make sure to send your nice message. Our audience is so amazing. You guys always send the best messages, so thank you. And as always, trust your Fentanyl wishing.

[Hannah]

I hope that's in your head, too. Love you.

[Mackenzie]

It.