The Girlfriends S5/E1: Shark Bait

Summary

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Podcast Summary: The Girlfriends S5/E1—"Shark Bait"

Podcast: The Girlfriends: Trust Me Babe
Episode: Season 5, Episode 1
Host: Anna Sinfield
Production: iHeartPodcasts and Novel
Release Date: April 13, 2026

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Episode Overview

The season premiere introduces the story of Wendy, a vibrant, witty single mom from Maui, who crosses paths with Derek Alldred—a charming yet mysteriously evasive man. Quickly, Wendy’s gut — supported by her sharp instincts and unbreakable sisterly bond — alerts her to cracks in Derek’s impressive facade. The episode explores themes of trust, women’s intuition, and the power of collective action, as Wendy and a growing circle of women begin to reckon with the discovery: Derek is a prolific romance scammer. This first installment sets up the journey from suspicion to investigation, culminating in the resolve to unmask Derek and protect others.

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Key Discussion Points & Insights

1. Setting the Scene: Wendy’s Date with Derek

• [01:57–04:36] Wendy recounts her 2013 date in Hawaii with Derek, who appears to be an ideal match: successful, attentive, with a knack for gripping stories (including a rare whale shark sighting).
  • Quote:
    • Wendy: “He was very charming, very attentive, very, very smart and very engaging.” [03:41]
• Red flag #1: Derek’s scuba story doesn’t match up with Wendy’s local knowledge. Pacific Whale Foundation doesn’t do scuba dives.
  • Quote:
    • Wendy: “He didn’t know this, but my daughter’s best friend’s parents owned Pacific Whale Foundation ... they don’t have scuba diving boats.” [05:34]
• Red flag #2: Derek claims he got the bends and went to a decompression chamber that doesn’t exist on Maui.
  • Quote:
    • Wendy: “... it really sounded a bit fantastical.” [06:30]

2. The Power of Gut Instinct & Sisterhood

• [07:59–13:04]
  • Anna introduces Wendy’s family: especially her sister, Laurie, who serves as Wendy’s “safety net.” The episode weaves in stories of intergenerational female solidarity and dating safety.
  • Laurie on their childhood: “That was a thing even back in the 60s, to keep each other safe, just in case.” [10:14]
  • The sisters establish routines for checking men out—leveraging technology, background searches, and relentless curiosity.
  • Laurie: “Every guy that she went out with, I’m going to see what I can find out about him.” [12:48]

3. Derek’s Shady Patterns: Love Bombing & False Details

• [14:11–15:01]
  • Derek’s affection escalates rapidly: offers to fly Wendy to meet his mother after two days, sends “100 reasons why I love you” (clearly copy-pasted).
  • Quote:
    • Wendy: “He literally didn’t even read it. He just googled 100 reasons to love someone and then just sent it to me.” [14:24]
• [15:51–17:05]
  • Derek tries to draw Wendy into a joint real estate investment within two weeks of meeting, suggesting, “let’s put both our names on it.” [16:41]
• [17:25]
  • Wendy: “Now they call it love bombing, but I didn’t know the term back then.”

4. Digging Deeper: Laurie Goes Detective

• [17:34–20:18]
  • Laurie investigates Derek’s business, discovering a brand-new, generic website, fake testimonials, and a business address that doesn’t exist.
  • Laurie: “I started noticing things that were static. They weren’t clickable.” [18:08]
  • She brings in her college friend, Pat, a private investigator.
  • Memorable moment:
    • PI Pat’s immediate advice: “Tell your sister to run. Tell her to run.” [20:18]

5. Confrontation and Escalation

• [22:48–27:24]
  • Wendy and Laurie review PI Pat’s findings: fake names, bogus business, multiple evictions—though nothing conclusive, it rings alarm bells.
  • Wendy confronts Derek; he dodges questions, spins lies, and even fakes hospital calls to maintain his stories.
  • Laurie: “But it was enough to know he’s not a good guy.” [24:10]
  • Wendy, driven by curiosity (and material for her dating memoir), continues to gather evidence.

6. Gifts, Manipulation, and More Lies

• [27:30–28:01]
  • Derek showers Wendy with extravagant gifts (roses, jewelry, sunglasses, a giant teddy bear), escalating the love bombing.
  • Wendy: “Who in their right mind would spend so much time and effort trying to con someone? It just didn’t make any sense to me.” [28:09]

7. Testing Reality: Lies & Proof

• [28:18–30:47]
  • Derek tries to prove his legitimacy with a staged house video and further emotional manipulation.
  • Sends a fake flight for Wendy’s San Francisco trip; pays for everything during her visit, yet money sources remain opaque.
  • Wendy starts questioning everything: “Does he really have a dog named Max? Is he even from San Francisco?” [28:18]

8. The Girlfriends’ Network: Power in Numbers

• [31:40–33:40]
  • Wendy’s girls’ night: her friends review the "case," share suspicions, and deliver a chilling wake-up call.
  • Girlfriend: “Wendy, he does sound like he is a psychopath. And what if he physically hurts you? What if he hits you? What if he kidnaps you?” [33:19]
  • Wendy: “It really made me open my eyes.” [33:37]
  • The emotional pivot from curiosity to concern for safety.

9. The Final Confrontations & Bizarre Twists

• [34:36–37:54]
  • Derek engineers one final manipulative gesture at a jewelry store—$4,000 earrings “for you, not my mother,” which Wendy flat rejects.
    • Wendy: “I do think that you are a con artist. And even though I can’t put it all together, I don’t ever want you to contact me again.” [36:06]
  • Derek impersonates his daughter via text after the breakup—Wendy catches on immediately.
    • Wendy: “I knew right away it wasn’t her because it’s texting like adults think teenagers text. No word is written out.” [36:44]

10. Persistence and Closure—But Not Quite

• [39:07–40:26]
  • Derek fakes cancer, sending Wendy a stock image ultrasound in a final bid to elicit sympathy.
  • Wendy: “I did a Google image search. The ultrasound picture that he sent me was one of the first ones that came up.” [39:41]
  • Refusing to be manipulated, Wendy blocks further contact, changing her WiFi password to the triumphant:
    • “Derek sucks my one ass.” [40:18]

11. A New Link in the Chain: The Next Girlfriend

• [40:38–41:07]
  • Weeks later, another woman, Cindy, calls Wendy — revealing that she too dated Derek. Wendy is pulled back in, her resolve to get answers reignited.
  • Wendy: “Baby, I’m gonna figure out what’s going on.” [40:53]

12. Tease for Next Episode

• [41:07–41:44]
  • Multiple voices preview what’s coming:
    • Laurie: “I can tell you neither one of us had any idea what he really was.” [41:22]
    • “We always say that. Trust your girlfriends.” [41:44]

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Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|---------|-------| | 03:41 | Wendy | “He was very charming, very attentive, very, very smart and very engaging.” | | 05:34 | Wendy | “They only do whale watching and snorkeling. They don’t have scuba diving boats.” | | 06:30 | Wendy | “…it really sounded a bit fantastical.” | | 10:14 | Laurie | “That was a thing Even back in the 60s, to keep each other safe, just in case.” | | 12:48 | Laurie | “Every guy that she went out with, I’m going to see what I can find out about him.” | | 14:24 | Wendy | “He just googled 100 reasons to love someone and then just sent it to me.” | | 16:41 | Wendy | “He started saying, you know, I really see this as our house. He’s like, let’s put both our names on it…” | | 18:08 | Laurie | “I started noticing things that were static. They weren’t clickable.” | | 20:18 | PI Pat | “Tell your sister to run. Tell her to run.” | | 24:10 | Laurie | “…it was enough to know he’s not a good guy.” | | 27:24 | Wendy | “The most basic word… and there was a typo in the word checking.” | | 28:09 | Wendy | “Who in their right mind would spend so much time and effort trying to con someone?” | | 33:19 | Girlfriend | “Wendy, he does sound like he is a psychopath. And what if he physically hurts you? What if he kidnaps you?” | | 36:06 | Wendy | “I do think that you are a con artist. And even though I can’t put it all together, I don’t ever want you to contact me again.” | | 39:41 | Wendy | “The ultrasound picture that he sent me was one of the first ones that came up.” | | 40:18 | Wendy | “Derek sucks my one ass.” |

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Structural Highlights

Strong Themes:

• Validation of gut feelings and female solidarity: “Trust your girlfriends.”
• The importance of proactively sharing information and looking out for one another.
• The complex tactics of love bombing and manipulation in romance scams.
• The difficulty—and necessity—of drawing boundaries in the face of persistent deception.

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Key Timestamps

• [01:57] – Anna’s content warning and introduction of Wendy
• [03:41] – Wendy meets Derek and red flags begin
• [07:59] – Wendy’s dating background and family safety strategies
• [12:48] – Laurie’s detective work begins
• [14:11] – Derek’s escalation: love bombing
• [17:34] – Laurie starts investigating Derek seriously
• [20:18] – Private Investigator Pat’s first warning
• [24:10] – “He’s not a good guy.”
• [28:09] – Wendy questions the logic behind Derek’s effort
• [33:19] – Friends vocalize real safety concerns
• [36:06] – Wendy formally confronts and rejects Derek
• [39:41] – Derek’s final failed scam (fake cancer)
• [40:38] – Call from Cindy reveals a network of ex-girlfriends

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Tone & Language

Anna Sinfield’s narration is wry and warm, blending suspense with empathy. Wendy’s reflective, candid, sometimes humorous storytelling, paired with the lively banter of her sister and friends, fosters relatability and keeps the tone engaging—even as it navigates dark or emotionally charged material.

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Summary

In "Shark Bait," the first episode of The Girlfriends: Trust Me Babe, we’re drawn into Wendy’s rollercoaster relationship with Derek, a seemingly perfect match who reveals himself in layers as a master manipulator. Through vigilant sleuthing, familial bonds, and the collective vigilance of women comparing notes, the true threat emerges. The episode is a testament to intuition, the necessity of friendship, and the rise of everyday women as justice-seekers—ready to expose romance scammers when no one else will.

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Transcript

[Anna Sinfield]

This is an I heart podcast. Guaranteed human.

[Liberty Mutual Spokesperson (possibly Doug or partner)]

And Doug, there's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual, even if it means sitting front row at a comedy show.

[Anna Sinfield]

Hey, everyone, check out this guy and his bird.

[Podcast Host or Guest (Serving Pancakes or similar)]

What is this, your first date?

[Charlamagne Tha God]

Oh, no.

[Liberty Mutual Spokesperson (possibly Doug or partner)]

We help people customize and save on car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird.

[Anna Sinfield]

Yeah, the bird looks out of your league.

[Liberty Mutual Spokesperson (possibly Doug or partner)]

Anyways, only pay for what you [e-mail] Liberty.

[Anna Sinfield]

Liberty. Liberty. Liberty.

[Charlamagne Tha God]

Peace to the planet. Charlamagne Tha God here. And listen, we are back. The Black Effect Podcast Festival is back in Atlanta on April 25th at Pullman Yard. Yeah, and the full lineup is nuts. We got the Grits and Eggs podcast, Deontay Kyle and Big Ice Cup Cat. We got Club 520 with Jeff Teague and the gang. Don't call me White Girl. Mona will be there. Keep it positive, sweetie, with Crystal Renee. We got Reality with the King with Carlos King. And yes, Drink champs will be in the plus. You know we gonna have a lot of guests, so you need to join us. And we got the Black Effect Marketplace, the picture podcast, and everything you expect from the Black Effect Podcast Festival. Tickets are on sale right now. Go get [e-mail] podcast festival. Don't play yourself. Okay, pull up.

[Anna Sinfield]

Then she says, have you seen a photo of my son? And I'm like, who is this person?

[Boys and Girls Podcast Host]

Welcome to the Boys and Girls podcast. Arranged marriage is basically a reality show. And auditioning for your soulmate. And who's judging? Only your entire family. I sacrificed myself to this ancient tradition hoping to find love the right way. And instead I found chaos, comedy, and a lot of cringe. Listen to boys and Girls on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast.

[Anna Sinfield]

No. Hey, girlfriends. Anna here. I just wanted to give you a quick heads up about what you'll hear in this season of the Girlfriends. The series touches on themes of coercive control. And there'll obviously be a little bit of swearing here and there too. But the women at the heart of this series are so funny and powerful and vivacious. And there's a great payoff at the end. For the full story, listen all the way through. If any of the themes feel difficult, you'll find links to mental health and support organizations in the episode. Description. Wendy is sitting poolside in a luxury hotel resort, listening to the sounds of waves crashing against the nearby beach. It's 2013 around the end of August and Wendy, the lucky devil, is in Hawaii. Wendy's in her early 40s and a single mom with a busy job. By the time she arrives, the sun has set over the Pacific and it's dark except for the glow of the tiki torches. Wendy's expectations for the evening had been pretty low. She's wearing yoga pants and it was too warm to bother with makeup. But now the balmy night air is alive with the buzz of possibility because Wendy is on a date and it's going well. Sitting across from Wendy is a successful businessman. Derek.

[Wendy]

There was something about him. He was very charming, very attentive, very, very smart and very engaging.

[Anna Sinfield]

He's explaining that he's on Maui for a little while to look at investment properties. He comes over regularly from San Francisco, hence the dating.

[Wendy]

He's in finance and he's a scuba diver and he loves to travel. He sounds like the perfect match for me.

[Anna Sinfield]

Wendy hasn't got the total hots for Derek. Looks wise. He kind of blends into the wash of faces that appear on dating apps. Short brown hair, slightly balding. Through absolutely no fault of Derek's, he is an entirely average middle aged white guy. But the conversation is flowing.

[Wendy]

He was talking about going scuba diving and he saw a whale shark.

[Anna Sinfield]

A whale shark sighting is rare on Maui. Derek is a lucky man. Taking his cue from Wendy's absorbed expression, he continues his story. There he is just off the coast, flapping his flippers on yet another unremarkable dive, when suddenly this gentle, speckled, flat headed sea giant glides past him. It was amazing. Amazing. As the tiki torches flicker around them, Wendy is gripped.

[Wendy]

I would die to see a whale shark.

[Anna Sinfield]

That is until Derek ruins it. He tells Wendy that he was scuba diving that day with a particular whale conservation group, a local, not for profit Pacific Whale Foundation.

[Wendy]

He didn't know this, but my daughter's best friend's parents owned Pacific Whale Foundation. And I said, I'm sure you didn't go on Pacific Whale foundation because they only do whale watching and snorkeling. They don't have scuba diving boats.

[Anna Sinfield]

It's such a small detail.

[Wendy]

And had he said, oh, you know what, I must be confused. It must have just had Pacific in the name. I would not have thought a second thing about it.

[Anna Sinfield]

But he would not let it go.

[Wendy]

No, it was Pacific Whale Foundation. He was adamant. So then he said he kept swimming down to try to spend more time with the whale shark and didn't quite do a safety stop.

[Anna Sinfield]

A safety stop? To release all the nitrogen his body had stored up while diving. Derek, our experienced diver, forgot he ended

[Wendy]

up getting the bins and he had to go to a decompression chamber. The only decompression chamber in Hawaii at the time was on Oahu. They don't have one on Maui, or they didn't at the time. I have not known a single person that ever got the bends or that ever had to go to a decompression chamber. I didn't call him out on that, but I thought, this is kind of weird and I've been scuba diving all over the world. Not to say it couldn't happen, but it really sounded a bit fantastical.

[Anna Sinfield]

Ever get that feeling in your gut like you're being lied to? Wendy has that feeling right now.

[Wendy]

I'm one of those people. I just can't let it go.

[Anna Sinfield]

Whale sharks, the bends, they're such inconsequential things.

[Wendy]

Why would you lie about that?

[Anna Sinfield]

It'll be five years, many more first dates, a federal investigation spanning states and decades, and a determined group of pissed off girlfriends raising hell before Wendy gets a satisfying answer to that question.

[Wendy]

My name is Wendy and I dated a con artist named Derek and it completely changed my life.

[Anna Sinfield]

I'm Anna Sinfield and from the teams At Novel and iHeart podcasts, you're listening to the Girlfriends. Trust me, babe. Episode 1 shark bait. When Wendy was young, her mum Sherry would share stories with her, tales from her youth about her own dating experiences. It's a Friday night in 1964 on the outskirts of Los Angeles. Sherry and her two housemates are at home in their first floor apartment. The smell of citrus blossom from the surrounding groves floats in the air. They're no older than 20, two recent college grads, and tonight one of them has a date. He's here. On date nights, these three friends have a bit of a routine. One of them tonight, it's Sherry, lets the suitor in, distracts him with aimless conversation while his date pretends to put the finishing touches to her hair. The third friend, with a bag full of trash from the kitchen, sneaks out the door and notes down the make, model and license plate of their guest's car. Safety protocol complete, the friend on the date leaves glammed up to the nines. Her two friends watch her cruise into the sunset with a stranger, safe in the knowledge that while they're probably just going to Shakey's for some dark beer and warm pizza, if, God forbid, something bad were to happen, they're prepared.

[Laurie (Wendy's sister)]

That was a thing Even back in the 60s, to keep each other safe, just in case.

[Anna Sinfield]

That's Laurie. She heard this story growing up, too.

[Laurie (Wendy's sister)]

We couldn't stand each other because, you know, sisters.

[Anna Sinfield]

Laurie is Wendy's older sister.

[Laurie (Wendy's sister)]

Our dad told us, one of these days, you girls are gonna be best friends. And we would gag and ew, gross. He was right. He was so right. Wendy always called me her safety net. And I love that. I love being her safety net.

[Anna Sinfield]

Wendy got married young to her college sweetheart, and they did the whole nine yards. Had a kid, got the white picket fence, and it was a great marriage, but it ran its course. By 35, Wendy is newly single and making a home for herself on Maui with her daughter. Everything feels new, especially dating.

[Wendy]

I'd never even been to a bar to have a guy buy me a drink. I didn't know about online dating. I didn't know about match.com.

[Anna Sinfield]

will you regale me with one of your dating stories?

[Wendy]

Ooh, I have so many Broke Bone Bobby and Jailbird Ryan and the Cuticle Picker, and I just have so many, right? Like, it's insane.

[Anna Sinfield]

As Wendy dives into the dating game headfirst, she tells her big sister Lori all about it over long phone calls. Wendy in Hawaii, Lori in Texas.

[Wendy]

He did not look like his photos at all. He was trying to take pictures of the sunset, and he kept using his flash. I get a letter from the county jail asking me to come visit him. I never told anyone that I was remotely interested in seeing a dick pic. Hordes of them. So many of them.

[Laurie (Wendy's sister)]

That's when I started realizing she needs a little backup.

[Anna Sinfield]

So in steps big sister Lori.

[Laurie (Wendy's sister)]

She allowed me to have her location on Google.

[Anna Sinfield]

At first, it doesn't all run as smoothly as their mother's trash run reconnaissance strategy.

[Laurie (Wendy's sister)]

I had to call her one time and say, your W is out in a lake.

[Anna Sinfield]

Wendy's Google Maps icon is surrounded by water.

[Laurie (Wendy's sister)]

I'm sorry, I forgot to tell you. It's a houseboat.

[Anna Sinfield]

The more Wendy dates, the more the sisters fall into a kind of rhythm.

[Laurie (Wendy's sister)]

Every guy that she went out with, I'm going to see what I can find out about him.

[Wendy]

I told him, I said, I'm okay to come to your home, but I'm having my sister look you up. And he goes, oh, try it. She's not going to find anything.

[Laurie (Wendy's sister)]

Challenge accepted.

[Wendy]

Here's the picture of his house. He's got these two kids, and it looks like he flies back and forth for these two cities.

[Anna Sinfield]

Oh, my God. Eight years and hundreds of first Dates later, Wendy has perfected her own strategies and is even planning to turn her bizarre dating stories into a book. It's the end of summer 2013, and it's been just two days since her first date with Derek the whale shark guy. And while she's still none the wiser as to why he'd lie about scuba diving, she's also kinda into him. He's successful, adventurous, and attentive, perhaps too attentive. He's been a prolific texter and emailer. Just two days after their first date, Derek offers to fly Wendy to San Francisco to meet his mother. He signs off his message, love you more than this morning with two exclamation marks.

[Wendy]

I said, you couldn't even name ten facts about me. And he then sent me an email, 100 reasons why I love you. Parts of it were, I love that you have to have a coffee first thing in the morning. I don't drink coffee. He literally didn't even read it. He just googled 100 reasons to love someone and then just sent it to me.

[Anna Sinfield]

Derek is a little carried away with his feelings, sure, but Wendy thinks maybe he's just kind of clumsy with it. We've all been a little cringy when we've had a crush.

[Wendy]

I was excited to meet someone that was very interested in me and was very open to me. That was very refreshing. Something just didn't feel completely right. But I wanted to like him.

[Anna Sinfield]

And so Wendy picks up the phone and makes a call to her sister in Texas.

[Wendy]

Can you check out Derek?

[Anna Sinfield]

Wendy and Laurie have been in the game for a while now.

[Wendy]

I had so many details. His name, how old he was.

[Laurie (Wendy's sister)]

She said, oh, he has a daughter, same age as my daughter.

[Wendy]

How long he said he'd been divorced,

[Laurie (Wendy's sister)]

the college that he went to, what year he graduated. She did get the name of the company he was working for.

[Wendy]

I don't even know that much information about some of my close friends.

[Anna Sinfield]

While Laurie gets to work online sleuthing, Wendy and Derek keep seeing each other. And one of those dates is in an upscale neighborhood where Derek is viewing a luxury condo.

[Wendy]

He had told me he's on Maui because he's looking for investments.

[Anna Sinfield]

It's been less than two weeks since they met.

[Wendy]

He said, do you want to go with me to look at some of these properties? So I'm like, yes, absolutely.

[Anna Sinfield]

They're walking through a place Derek is considering investing in. It's a three bed property with all the amenities, Ocean views, built in, lighting fixtures, for hanging your own art collection. It's classy. Wendy's realtor friend is showing them around.

[Wendy]

Oh, wow. He seems like such a great, successful, nice guy.

[Anna Sinfield]

But before long, Derek fumbles into weirdo behavior again.

[Wendy]

He started acting like, oh, this could be our home.

[Anna Sinfield]

Our home.

[Wendy]

And I'm like, I thought this was a real estate investment thing. He started saying, you know, I really see this as our house. He's like, let's put our both our names on it. I'm like, what? He goes, I want to make sure you and your daughter are taking care of him. Like, well, then put me in your will. I'm never signing anything with you.

[Anna Sinfield]

This is the moment at which Wendy's interest in Derek as a possible boyfriend really takes a turn. Whatever his charms, he is coming on too strong. It's not just the real estate business. He's sending shared calendar invites for upcoming family visits.

[Wendy]

Now they call it love bombing, but I didn't know the term back then.

[Anna Sinfield]

Wendy's big sister, Lori, is starting to question Derek, too. In a small, narrow room of her bedroom, Lori is at a cluttered desk. She's sitting on one of those ergonomic backless chairs where you rest your weight on your knees. She's looking at the website for Derek Allred's real estate investment company, the one he sent Wendy. Scrolling to the bottom of the page, she notices the site was only created that year. Could be something, could be nothing.

[Laurie (Wendy's sister)]

I started noticing things that were static. They weren't clickable.

[Anna Sinfield]

It's full of testimonials, generic stock images, but the links are dead. Are these real people? For that matter, is a business real? Laurie finds the company's address on the website.

[Laurie (Wendy's sister)]

I went to Google Earth and I went down to street level, and in that building, you could see the directory of what companies were in that building.

[Anna Sinfield]

Derek's supposed company wasn't there. Other than the stuff Derek's provided to Wendy himself, Laurie can't find any detail whatsoever on the guy.

[Laurie (Wendy's sister)]

This puzzle was missing a lot of pieces. I just was not finding the normal things that I could find.

[Wendy]

Why am I stuck?

[Laurie (Wendy's sister)]

Why can't I find more on this guy?

[Anna Sinfield]

As she sits alone at her desk, a new thought occurs to Laurie. Maybe the lack of information, the very existence of so many strange gaps, is the enormous, frantically waving red flag she's been looking for. Laurie decides it's time to call in a little backup of her own. She looks up a name and number that she hasn't thought about for years, gives him a call.

[Laurie (Wendy's sister)]

I recognize that voice immediately.

[Anna Sinfield]

Laurie's old College pal Pat is now a private investigator. Private investigator Pat, he said, of course

[Laurie (Wendy's sister)]

I will do this. Of course I will do this for you, PI.

[Anna Sinfield]

Pat gets to work right away, pulling off his own research tools while the two old friends sit on the phone. And in almost no time at all, the computer spits back some results.

[Laurie (Wendy's sister)]

He said, just from looking at this report. Tell your sister to run. Tell her to run.

[Liberty Mutual Spokesperson (possibly Doug or partner)]

And Doug, there's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual. Even if it means sitting front row at a comedy show.

[Podcast Host or Guest (Serving Pancakes or similar)]

Hey, everyone.

[Anna Sinfield]

Hey, everyone. Check out this guy and his bird.

[Podcast Host or Guest (Serving Pancakes or similar)]

What is this, your first date?

[Charlamagne Tha God]

Oh, no.

[Liberty Mutual Spokesperson (possibly Doug or partner)]

We help people customize and save on car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird.

[Anna Sinfield]

Yeah, the bird looks out of your league anyways.

[Liberty Mutual Spokesperson (possibly Doug or partner)]

Only pay for what you [e-mail] Liberty.

[Anna Sinfield]

Liberty. Liberty. Liberty.

[Podcast Host or Guest (Serving Pancakes or similar)]

On the Serving Pancakes podcast, conversations about volleyball go beyond the court. Today we have a little best friend compatibility test. Okay, and how long have we been best friends for? Since the day we met. As the League1 volleyball season heads towards its final stretch, there's no better time to tune in. We really are like yin and yang, vodka and tequila. You'll hear unfiltered analysis, behind the scenes stories and conversations with leaders making an impact across the sport. Today we have Logan Lednecki. I feel like our fan base in general is very connected. It's like a comforting feeling getting to play at home. Whether you're following the final push of love season or just love the game, serving pancakes brings you closer to the action and the people shaping the future of volleyball. Jordan Thompson had that microphone out. God forbid we make mistakes or cuss at our coach. Like when talking. Open your free iHeartradio app, search serving pancakes and listen. Now, this has been serving pancakes. And we'll catch you on the flip side.

[Anna Sinfield]

Okay.

[Wendy]

Presented by Capital One, founding partner of iHeart.

[Silk Protein Advertiser]

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[Anna Sinfield]

Laurie's just got off the phone with PI Pat, who has told her in no uncertain terms to get her sister the hell out of her weird dance with Derek Allred. With Pat's report sitting in her inbox, Lori reaches for the phone again. In her panic to tell Wendy the news, she nearly falls off her chair.

[Wendy]

I was really disappointed that there wasn't more information about this. There wasn't anything really big. And I kind of my shoulders dropped.

[Anna Sinfield]

You see, the report PI Pat sent over didn't really answer Wendy's questions. It just gave her more. Firstly, Derek had been lying to Wendy about the spelling of his name. Derek Allred was Derek Alldred. That's how Pipat had found him. Secondly, Derek Alldred had a long list of previous addresses. Oddly long. And across states as well as that a larger than average number of evictions. And that's pretty much it.

[Wendy]

I thought for sure we're going to find out there's something going on here.

[Anna Sinfield]

For Wendy, it doesn't seem like much. For PI Pat and Laurie, reading between the lines, it says a lot. There were no felonies, but PI Pat can explain that.

[Laurie (Wendy's sister)]

He said I can't see certain reports because states don't share the information. But it was enough to know he's not a good guy.

[Anna Sinfield]

But Wendy's moved beyond wanting to date Derek. She has other ambitions.

[Laurie (Wendy's sister)]

She has this thing. She considers herself a karma warrior. Okay, Meaning in her mind, this is a guy that needs to be put in his place. The toxic masculinity guys go for it. Wendy, say what you need to say, do what you need to do. This guy was totally different. Attractive, friendly, helpful. All these things, those are the ones that, you know, scare me. And I think she thought, eh, I'm just gonna play with them a little bit just because she could.

[Anna Sinfield]

Wendy, with a penchant for poking the bear and the final chapter of a book about online dating to write, sets out to find the truth. Wendy meets up with Derek armed with evidence from PI Pat and Deputy PI Laurie. It doesn't really go according to plan because Derek cops to none of it. The long list of previous addresses.

[Wendy]

Oh, I'm in real estate investment. Those are properties I've owned and rented.

[Anna Sinfield]

The eviction notices I've had to evict other people. Derek even calls Maui Memorial Hospital while Wendy is on speakerphone beside him to prove he really was in hospital around the time of his story about getting the bends.

[Wendy]

He did not own up to anything that was remotely off. He had an answer for everything.

[Anna Sinfield]

Without cold hard proof, all she has is gut instinct. And in the face of Derek's confident self assuredness, it's not the satisfying confrontation she had hoped for. Wendy just has more questions.

[Wendy]

Why is he coming after me? I kept thinking maybe there's something to do with buying a house. But I don't have a lot of extra cash sitting around. It's not like I was super wealthy or anything.

[Anna Sinfield]

It's only been a couple of weeks. But Wendy is clear on one thing. Derek is not investing in the Maui property market.

[Wendy]

That whole deal fell through because he didn't have money. My friend was the realtor. She's like, there's no money in that account. I'm a super curious person. So I kept agreeing to meet with him now and then I would go with him to look at condos and he would talk about how much money he had. One time he said, I know you don't believe me. And he had pulled up an investment account, like 1.2 million. First of all, it looks like a PDF. And then I also noticed that there was a typo in the word checking. The most basic word.

[Anna Sinfield]

And yet all the while, he's lavishing her with attention and more.

[Wendy]

One, two, three dozen roses, Sherry's berries, Tiffany jewelry, prescription sunglasses, a giant teddy bear.

[Anna Sinfield]

To give you a sense of scale, I'm 4 foot 11 and I'd call this bear Daddy.

[Wendy]

If he would have been just any other person, I would have stopped. But because I had already started writing a book about online dating, I kept going with it.

[Anna Sinfield]

She doesn't just want Derek to admit that he's a liar. She wants him to explain why he's lying.

[Wendy]

Who in their right mind would spend so much time and effort trying to con someone? It just didn't make any sense to me.

[Anna Sinfield]

Wendy is starting to doubt whether anything Derek says is true. Does he really have a dog named Max? Is he even from San Francisco? And if so, where does he actually live? In response to Wendy's questions, Derek sends Wendy a video tour, padding around the inside of a home. We start off in a living room and there's some red walls. He walks through a doorway into a kitchen. Lots of pictures, a nicely made up bed. There's a dog bed in the living room, and the name on the back says Maxwell. But what does a random video really tell you? It's like if someone said to me, anna, you're not really a vegan. And to prove to them that I am, I send them a video of a salad. Everyone eats salads. Who's to say it's even my salad? Who's to say I even took the video? But whenever Wendy Pushes too hard with questions or challenges about Derek's metaphorical salad. He seems to find ways to derail things in his favor.

[Wendy]

There was always some tragic thing that was happening. One time he told me his dog died. He would have drama in his life. He just wouldn't let it go. He still kept trying.

[Anna Sinfield]

Wow. He just would not quit.

[Wendy]

Right?

[Anna Sinfield]

Did he like it? You know, the rejection?

[Wendy]

I don't know, Wendy. I've been nothing but transparent with you, and I love you. And it really is so hurt that you're saying these things about me. Once I knew he was a pathological liar, I really just wanted to catch him in a way that he couldn't get out of.

[Anna Sinfield]

Isn't until mid October that Wendy gets her next opportunity to try and figure out what Derek's really up to. And this time it's on his home turf. Wendy has to travel to San Francisco for a biopsy following a breast cancer scare. When Derek hears about it in classic Derek style, he makes a big fuss, offering to buy Wendy's plane ticket. And then sending details for a flight that doesn't exist. Didn't he think you'd find out about the flight?

[Wendy]

You would think so. I have no idea why he would do some things and not others.

[Anna Sinfield]

She gets there anyway, under her own steam. The biopsy results come back negative within a couple of days, and Wendy's feeling good. Then Derek pops up again. He invites her to dinner. Wendy can't resist the opportunity to do a bit of sleuthing on Derek's patch. They go for the dinner, and not only does he rock up in a BMW, he actually pays for everything. He even takes Wendy to a Bryan Adams concert. Merch drinks, all paid for by this strange man.

[Wendy]

I'm sitting there going, well, he looks like what he told me he was. I was trying to figure out, like, where did he come into money?

[Anna Sinfield]

Wendy looks at the man beside her and asks herself for maybe the hundredth time, what kind of con is this? It's a Tuesday evening in the very middle of October. Wendy is back on Maui and the Prosecco is flowing. A medley of dance pop albums play in the background. Brittany, Madonna, Lady Gaga. There are potluck snacks on Wendy's living room table. It's been a month and a half since Wendy's first date with Derek. And it's girls night. There are eight women crammed into Wendy's small living room, gawping at the giant TV on the wall. The show Wendy's Love Life. She's hooked the TV up to her phone and is doing a full class report of her latest dates with supplementary screenshots and selfies.

[Wendy]

All my girlfriends were getting the reports about what was going on, and they were all invested.

[Anna Sinfield]

There's nothing quite as intoxicating as being the headline act at girls night. And the last few weeks have given Wendy a lot of material to work with. As she regales them with her latest tales, the girls speculate about Derek's motives.

[Wendy]

What is this guy's deal? What is he after?

[Anna Sinfield]

Until finally, one of Wendy's girlfriends says the thing we've all been thinking,

[Wendy]

Wendy, he does sound like he is a psychopath. And what if he physically hurts you? What if he hits you? What if he kidnaps you? Up until she said that, it had never crossed my mind.

[Anna Sinfield]

It's the same worry Wendy's sister had quietly all those weeks earlier.

[Wendy]

It really made me open my eyes.

[Anna Sinfield]

It's been two months of exchanges with Derek, and despite all the evidence, all the difficult questions, Wendy is no closer to learning the truth about who this man actually is. But now she realizes, really realizes,

[Wendy]

this is clearly an unhinged person, and maybe I'm not safe. I'm just never going to figure this out. I need to get him out of my life before he does do something really crazy to me.

[Anna Sinfield]

It's only been a couple of days since Wendy's girls told her gently to leave Derek well alone. When he reaches out again, wanting to meet up, Wendy does decide to go. Maybe this is her chance to end it in person.

[Wendy]

He asked me to come meet him because he wanted to get his mother a birthday gift.

[Anna Sinfield]

Wendy meets Derek at the jewelry store in a busy shopping center, and at first she browses solo while Derek does his own thing.

[Wendy]

And then he's like, oh, hey, I think I found the gift for my mom.

[Anna Sinfield]

Derek shows her a pair of diamond stud earrings, $4,000.

[Wendy]

And he goes, would you try them on? They're just diamond studs. Everybody knows what they look like on ears, but I put them on. And then he goes, well, let's look out in the light. And he was trying to pull me outside of the store.

[Anna Sinfield]

Wendy looks over at the salesperson for help, but they just nod. I imagine with the patience of all underpaid retail workers who are unwillingly roped into romantic gestures. Gestures. Outside the jewelry store, under the bright lights of the shopping mall, Derek makes his reveal.

[Wendy]

I've already paid for them. They're for you, not my mother. I want to do it to show you that I'm committed to this relationship.

[Anna Sinfield]

She comes in here to end it, and now he's throwing earrings at her.

[Wendy]

And I'm thinking, where is this coming from? I gave him back those earrings. I said, I do think that you are a con artist. And even though I can't put it all together, I don't ever want you to contact me again.

[Anna Sinfield]

A few weeks later, Wendy gets a text.

[Wendy]

Hi, Wendy, I'm on island. My dad doesn't want me to contact you, blah, blah, blah.

[Anna Sinfield]

It's from an unknown number and the text that claims to be not Derek, but Derek's daughter.

[Wendy]

I started laughing. I knew right away it wasn't her because it's texting like adults think. Teenagers text. No word is written out.

[Anna Sinfield]

Wendy even shows them to her own daughter.

[Wendy]

Do you think this is actually from a teenager? Oh, gosh, no. We don't really text like that.

[Anna Sinfield]

The unknown number sends a follow up.

[Wendy]

Oh, my dad would be upset if he knew I was reaching out to you, but he's in the hospital.

[Anna Sinfield]

Wendy resolutely broke up with Derek, but this is too good of an opportunity to pass up.

[Wendy]

I call the hospital, he is registered as the patient. I'm like, what?

[Anna Sinfield]

Wendy's own daughter wants answers now too.

[Wendy]

She goes, you gotta go down there. You can catch him because you know his daughter's not there. I drive to the hospital and I go in the room and I see him and I'm thinking, where's your daughter? Oh, my friend on island took her. They went to Starbucks. And I'm like, oh, Starbucks closes in like 20 minutes. It's Maui. Everything closes by 9pm if not earlier.

[Anna Sinfield]

Derek has taken off to get a scan. Wendy sits in his room waiting. 20 minutes go by.

[Wendy]

Starbucks is closed. Where's your daughter? He just kept saying, oh, well, they must be doing this or that or whatever. And she just didn't come. And so I'm like, okay, you know what? Whatever. I gotta go home.

[Anna Sinfield]

Wendy doesn't go home because it's time for a good old fashioned stakeout.

[Wendy]

I went and I parked my car across the street.

[Anna Sinfield]

Wendy sits in her car in the dark, eyes trained on the bright fluorescent lights of the hospital main entrance, and waits.

[Wendy]

He got discharged and I saw him come out of the hospital in plain clothes and then just started walking down the street. He didn't have a vehicle, he didn't have anything. There was nobody to pick him up.

[Anna Sinfield]

Wendy was right. Derek's daughter is nowhere to be seen. But as she watches him retreat into the distance, she's no closer to finding out the truth.

[Wendy]

It really was a bummer because nothing made sense. It killed me to not have answers and to just say that I'm never going to have correspondence with him again.

[Anna Sinfield]

Back in San Francisco, Derek takes a little longer to drop it. He keeps sending emails, which Wendy doesn't reply to. He even tries one last sympathy play, telling her that he in fact has cancer, that she's the love of his life, that he loves her forever. Attaching copies of his ultrasounds as proof.

[Wendy]

I did a Google image search. The ultrasound picture that he sent me was one of the first ones that came up.

[Anna Sinfield]

Oh, wow. So he didn't even try hard.

[Wendy]

He wasn't trying hard. He wasn't putting in the effort like he used to. I just felt like that was his attempt to lure me back in. And I didn't take the bait.

[Anna Sinfield]

Instead, she resolves not to respond to Derek ever again, to close the chapter without answers, she sits down at her computer and changes her WI fi password

[Wendy]

to the immortal words, Derek sucks my one ass.

[Anna Sinfield]

Wendy is done. Months later, Wendy is walking down Maui's busiest street when her phone rings.

[Wendy]

Hi, Wendy. You don't know me, but my name's Cindy and we both dated. Derek and I was like.

[Anna Sinfield]

And just like that, Wendy's back in.

[Wendy]

Baby, I'm gonna figure out what's going on.

[Anna Sinfield]

Coming up on the Girlfriends. Trust me, babe,

[Podcast Host or Guest (Serving Pancakes or similar)]

Something's off about this whole thing. Something's fishy.

[Wendy]

She was relentless. He is not gonna get away with this. It sounds so familiar. She kept saying, can you text her and see if you can get a picture of him? And she did.

[Laurie (Wendy's sister)]

I can tell you neither one of us had any idea what he really was.

[Anna Sinfield]

A terrible, middle aged, nearly balding boyfriend pops up in Minnesota. Bad news.

[Podcast Host or Guest (Serving Pancakes or similar)]

We don't like him.

[Wendy]

He kind of gave me creepy vibes

[Anna Sinfield]

and runs into a group of no nonsense, pocky loving nurses.

[Podcast Host or Guest (Serving Pancakes or similar)]

We still talk about it.

[Anna Sinfield]

We always say that.

[Podcast Host or Guest (Serving Pancakes or similar)]

Trust your girlfriends.

[Anna Sinfield]

You. I got you. I got you. The Girlfriend's Trust Me Babe is produced by novel for iHeart podcasts. For more from Novel, visit Novel Audio. The series is hosted by me, Anna Sinfield. It's produced by Leona Hamid. Our assistant producer is Valeria Rocker. Our editor is Jo Wheeler. Production management from Cherie Houston, Joe Savage and Charlotte Wolf. Fact checking by Dania Suleiman. Sound design, mixing and scoring by Daniel Kempson and Nicholas Alexander. The Girlfriend's theme was composed by Daniel Kempson and Louisa Gerstein and performed by Daniel Kempson with vocals by Louisa Gerstein. Music supervision from Daniel Kempson and Anna Sinfield. The series artwork was designed by Christina Lehmkul, story development by Susie Baker and Olivia Smart. Novel's director of development is Selena Mehta, Max o' Brien is the executive producer for Novel, Katrina Norvell and Nikki Etor are the executive producers for iHeart podcasts, and the marketing lead is Alison Cantor. Special thanks to Carrie Lieberman and Will Pearson at iHeart podcast. Julie Sensulo, Ann Langston, Carolyn Shirlevin, Katie Gillis, Kelly Hunt, Rachel Munro, Tom Oldag, and Tad Vesna. This is an I heart podcast. Guaranteed human.