Why Dating Feels So Negative Right Now ft. Matchmaker Maria

Summary

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U Up? – Why Dating Feels So Negative Right Now ft. Matchmaker Maria

Podcast Hosts: Jared Freed (in for Jordana Abraham during her maternity leave)
Guest: Matchmaker Maria
Release Date: February 13, 2026

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EPISODE OVERVIEW

In this Valentine’s-themed episode, comedian Jared Freed is joined by renowned dating coach Matchmaker Maria for a lively, candid conversation about the current dating climate and why it feels particularly negative in 2026. They delve into generational dating attitudes, the impact of technology and algorithms, authenticity versus cynicism, and the emotional rollercoaster of Valentine’s Day. The episode is rich with real-world insights, playful banter, and practical advice—plus listener questions about communication, expectations, and setting boundaries in modern relationships.

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KEY DISCUSSION POINTS & INSIGHTS

1. Attitude and Negativity in Dating Today

• Maria’s front-line perspective: Maria shares that more and more singles approach dating assuming people are acting in “bad faith.” The trend of taking quick screenshots for social media validation (e.g., Threads) perpetuates cynicism over curiosity. (04:00)

  "If you're so quick to think that the person who's messaging you is coming out in bad faith... it's just coming in bad faith to the whole experience. And I think the attitude has to shift a little bit. Like, if you're going to do that, just log off."
  —Matchmaker Maria (04:10)

• Jared’s observation: Even those who claim not to post act “as if they’re online,” imitating behaviors and attitudes they see in digital spaces, creating a “weather” of negativity. (04:32)

2. Algorithmic Dating & Siloed Realities

• Maria notes the profound effects of dating apps and social media algorithms, which reinforce personal biases and create “siloed” dating environments:

  "You've engineered your algorithm to only show you this aesthetic, so you have no concept of what you're actually attracted to versus what you think you're attracted to."
  —Matchmaker Maria (02:44)

• Jared likens dating trends to the evolution of drink trends (rose → seltzer → espresso martinis), suggesting that attitudes shift in cycles. (03:22)

3. Generational Differences: Gen Z, Millennials, and Beyond

• Maria compares her experience working with Boomers, Gen X, Millennials, and now Gen Z daters:
  • Gen Z is marked by either feeling immense romantic pressure (“I’m 26, not married, is it over for me?”) or aloofness about commitment (“Can we wait two months to meet? I don’t want kids for 10 years.”). (08:18)
  • Gen Z highly values authenticity over appearance or traditional markers—this is confirmed by studies and her firsthand experience. (12:56)

  "They judge you on authenticity. No other generation has that as their number one factor."
  —Matchmaker Maria (12:56)

4. Valentine’s Day: Myths, Realities & How to Navigate

• Jared calls Valentine’s Day a “shouted down” holiday, with predictable takes each year. He and Maria discuss real expectations for singles and couples:
  • Being single on Valentine’s Day: Acknowledgement (or lack thereof) is a clear social signal of relationship status. No acknowledgment? “Consider yourself single.” (16:30)
  • Suggestions for singles: Go to local bars—they’re the “poppiest” they ever get for meeting fellow singles during this window. (15:23)

  “Today and tomorrow are the sluttiest days for single...The people that are coupled up—they’re not at your local dive bar."
  —Matchmaker Maria (15:50)

  • Coping advice: You control your narrative—embrace it, don’t feel forced into loneliness, and “lean in” to solo plans or spontaneous connections. (16:53)

5. How to Handle Dating Holidays Early On

• Game segment: “What Should Happen on Valentine’s Day?” for relationships at various stages—practical scripts and comfort-level advice.
  • After three dates in a month, someone should bravely, but honestly acknowledge the holiday and set expectations.
  • One-month relationships with a label? Celebrate! Six months, no label? "That's a situationship, maybe a 'you up?' text," jokes Maria. (24:08 – 26:55)

  “You have to set up people for success so that they meet whatever expectation you might have in your head.”
  —Matchmaker Maria (24:29)

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NOTABLE QUOTES & MEMORABLE MOMENTS

• On negative attitude and metacommentary:

  "The general vibe of it wasn’t her own. She’s speaking within the zeitgeist, with the safety of that environment."
  —Jared Freed (05:54)

• On authenticity as a dating value:

  “There was a Match Group study conducted to figure out what Gen Z is valuing, and by far, it was authenticity.”
  —Matchmaker Maria (12:56)

• Valentine’s as a litmus test:

  “When something doesn't get done for you or an acknowledgment of the day, if there's no acknowledgment of the day, then there's no acknowledgment of you. So consider yourself single.”
  —Jared Freed (16:35)

• On healthy vs. unhealthy relationship communication (re: using a shared gift card solo after bf’s refusal to celebrate):

  “Healthy relationships are dependent on these bids to connect. You need lots of happy, positive bids... Instead of telling him ahead of time, you did it to be petty. That’s not healthy.”
  —Matchmaker Maria (38:59)

• On the spirit of compromise and not using ‘morality’ to shut down discussion:

  “Anytime someone tries to bring morality into a discussion, they’re no longer discussing, they’re now trying to win.”
  —Jared Freed (34:40)

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LISTENER Q&A & PRACTICAL ADVICE

How to Communicate Boundaries About Sex, Especially on Holidays (51:24)

• Maria’s 12 date rule: Designed to let people explore compatibility emotionally, not just physically. The rule is not a “goal,” but a framework to clarify feelings and keep perspective.
  • “It’s OK to say, ‘I’d love to come over, but I’m not ready to get to that level of intimacy yet.’ That’s normal.” (52:29)
  • Maria notes that good partners are responsive to honesty—a negative reaction is a red flag, not a failure of your boundaries.

  “If you’re scared that they’re going to be upset you don’t want to have sex, you shouldn’t be going over to their house if you don’t trust that they can handle their emotions.”
  —Matchmaker Maria (51:56)

What If My Partner Refuses to Celebrate Valentine’s Day? (38:33)

• Maria and Jared agree: Celebrating something your partner enjoys is part of being a supportive partner—it’s not about “winning.”
  • Both find the “consumerism” argument a tired excuse for pettiness.
  • Maria: “The moment one of you likes it, you have to celebrate it.” (36:46)
  • If you’re having the same conflict every year, “You’ve outgrown this relationship.” (41:09)

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TIMESTAMPS FOR IMPORTANT SEGMENTS

• [02:44] Algorithms and aesthetic traps in dating
• [04:00] Attitude and bad faith in dating apps
• [08:18] Gen Z attitudes: “No time” vs. “all the time in the world”
• [12:56] Gen Z & authenticity
• [15:23] Where singles should go on Valentine’s Day
• [16:30–16:53] Valentine’s Day authenticity test
• [24:08] Relationship “game”: How to handle Valentine’s at 1/3/6/12 months
• [34:40] Weaponizing “morality” and consumerism as arguments
• [38:33] Petty or Prudent game: Using the spa gift card solo
• [51:24] How to communicate sexual boundaries without “killing the mood”
• [55:25] 12 date rule—don’t use it to dodge difficult truths

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CLOSING THOUGHTS AND CALL TO ACTIONS

• Be intentional, honest, and authentic in your approach to dating.
• Release cynicism and online-inspired snark in favor of genuine curiosity.
• Celebrate your partner's joys, even if you wouldn't have chosen them.
• Communicate your boundaries clearly—you’ll attract the right partners by being upfront.
• Don’t get stuck in patterns or games—relationship health requires flexibility and connection bids, not scorekeeping.

“You either want to be right, or you want to be happy.” —Matchmaker Maria (39:46)

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RESOURCES & FURTHER LISTENING

• Follow Matchmaker Maria on all platforms, check out her “Ask a Matchmaker” podcast and her book.
• Jared Freed’s new book is out, with insider details on ‘the mind of the dater.’
• Find the U Up? podcast, bonus content, and more @u.up.podcast on Instagram and on YouTube.

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Episode captures the reality of 2026 dating—algorithmically fragmented, craving authenticity, and still as emotionally fraught as ever, especially near Valentine’s Day. Full of real advice, laughs, and empathetic truths, it’s a must-listen for singles and couples navigating the modern landscape.

Transcript

[Podcast Host/Announcer]

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[Matchmaker Maria]

The three Gen Z kids at the Today show, it was so humbling for me cuz they're like, like they didn't know who I was. They didn't know I had this is my career. They didn't know anything. And it was just like, are you excited to be on tv? And I'm like, I'm excited for this opportunity, but I've been on live TV before. You have. And I'm like, okay.

[Jared Freed]

It's also demeaning, like, don't talk to me like that. Hello and welcome to the UWA Podcast. I'm Jared Freed.

[Matchmaker Maria]

And I'm Matchmaker Maria.

[Jared Freed]

And it is so good to be back here with you, Matchmaker Maria. And you the listener, the viewer. If you're on YouTube, thank you for watching. If you're just listening, thank you for listening. We are here during our maternity leave era for Jordana Abraham. If you want to hear from Jordana and get updates, sign up for you up with benefits. That's five bucks a month, gets you two extra podcasts A month, no ads a day, early release on the episodes. And again, you're going to hear from Jordana and how she's doing with the whole baby process. And we wish her the best and all the love in the world. But today, Matchmaker Maria, it's so good to have you here.

[Matchmaker Maria]

Thank you for having me. I love that you called it the baby process.

[Jared Freed]

The baby process, yeah. What would I call it? The baby thing. The baby. What would you call it?

[Matchmaker Maria]

Being a mom. Mothering.

[Jared Freed]

Mothering. Mothering sounds so formal. I guess. Baby process.

[Matchmaker Maria]

Human shouldn't be a little formal, I guess.

[Jared Freed]

I don't know. I, I would be like for a baby. I'm like that it.

[Matchmaker Maria]

I'm excited to hear these episodes. As a subscriber, I love, first of all, listening to the podcast without any ads.

[Jared Freed]

Yes.

[Matchmaker Maria]

But also I can't wait to hear about Jordana's experience, because I can relate to it.

[Jared Freed]

Yes, you've done it.

[Matchmaker Maria]

As someone who's been mothering for eight years with.

[Jared Freed]

For two. Two. Two experiences.

[Matchmaker Maria]

Two experiences.

[Jared Freed]

Two children sitting at home, two mouths to feed, having two children.

[Sponsor/Ad Voice]

Yeah.

[Jared Freed]

How does that change your perspective on the dating world? I mean, like, that's something as a single guy, you hear back from people with kids. Nothing's that serious. All your problems are nothing. Which kind of, for some, you know, that's not everybody. You, as a professional, understand not to be like, well, it's nothing. You don't have to, you know, you don't have two kids.

[Matchmaker Maria]

But my meter is way more sensitive since having kids, so I can kind of sniff out when I'm talking to someone who's me, you know, what they're looking for. And I'm like, is this what you really want, or is this what you think you're familiar with? Because you've engineered your algorithm to only show you this aesthetic so you have no concept of what you're actually attracted to versus what you think you're attracted to.

[Jared Freed]

Give me an example of that. Is that mostly men?

[Matchmaker Maria]

Yeah.

[Jared Freed]

Yeah. So men come to you and say, I want this, this, and that. And you're like, have you seen that?

[Matchmaker Maria]

Do you really want. I mean, I'll introduce you to that person if they also want to meet you, but I don't know if that's actually going to work for you.

[Jared Freed]

What's the toughest part about dating right now? What's the thing people are dealing with? It's 2026. What's, like the thing. You know, I think there's like, every year it's like. It's like the new. The new alcoholic drink. You know, we go from rose to spike seltzer to the espresso martini. I think there's. This happens in dating. What, in your. Your ear, to the ground, your front lines?

[Podcast Host/Announcer]

What do you.

[Jared Freed]

What's the thing in dating right now that people are dealing with?

[Matchmaker Maria]

So as someone who talks to 40 single people a week via Zoom or in person for really in depth interviews about what they're looking for, who they want to date, what their dating history looks like. I know that last year when I was on, I said something about, like, algorithms are keeping people single because we all have these very different realities, but I also think that in 2026, it's also about attitude. And I feel like if you're so quick to think that the person who's messaging you is coming out in bad faith. And you're just ready to say something smart so that you can take a screenshot of it, post it to Threads, let the whole algorithm on that platform, you know, support you, or, you know, oh, yeah, you did it. It's just coming in bad faith to the whole experience. And I think the attitude has to shift a little bit. Like, if you're going to do that, just log off.

[Jared Freed]

Well, honestly, you know, to make it even more relatable to, to someone who's like, I would never post on anything. But if you, if your first move is to do what you've seen has been posted, you know, like, it's, it's the environment, it's the weather, the negativity does feel palpable. I mean, you know, we did a you up with benefits episode where we had two Gen Z, a Gen Z couple come on, and they were, they were discussing the time they were spending together. And like, I was, like, I thought the woman in the scenario was being mean. Like, I thought she was being mean to the guy. Like, she was like, it's embarrassing. Her boyfriend is on with us right now. Like, and then you can go listen to the interview and I, I, I give her some feedback that my feelings are my feelings. You can disagree with them. But I'm saying, when I heard her say, like, having a boy, like, who wants to have a boyfriend, like, as he's on the zoom with us, and she's kind of giving to. And I'm like, like, I'm tasting it and I'm going, well, I know the joke she's doing. I know where she learned this is a boyfriend.

[Matchmaker Maria]

Is having a boyfriend embarrassing?

[Jared Freed]

Right? And just the general vibe of it wasn't her own. It was more like, I'm speaking within the zeitgeist. I'm speaking within.

[Matchmaker Maria]

So that's it right there. She's speaking in that environment.

[Jared Freed]

The safety of the zeitgeist in the environment. Right? And I think what you're saying, and.

[Matchmaker Maria]

Men do this too.

[Jared Freed]

Everyone does.

[Matchmaker Maria]

Everyone does it, you know, and it's not, and it's not even. And I don't think it's even limited to a generation. We've all done it. It's just the difference now is that we're no longer in monoculture culture. Like, not all of us are spending Friday nights at home to watch tgif. And what is Steve Urkel going to do today? Like, that's not how I do wonder.

[Jared Freed]

What Steve Urkel is going to do today. What do you think Steve Urkel's doing?

[Matchmaker Maria]

How did he not blow up? Is it J. White?

[Jared Freed]

I mean, he did blow up. If you think about. For one thing, sometimes people only want you to be one.

[Matchmaker Maria]

Like M. Culin, who I think is so talented. I wish I could.

[Jared Freed]

I mean, M. Cin to do to. To lead a whole movie. You ever see like the snl?

[Matchmaker Maria]

Yeah.

[Jared Freed]

Like when he hosted snl, you're like, oh my God, this person.

[Matchmaker Maria]

I mean I've been just seeing him at the Golden Globes last month.

[Jared Freed]

I didn't watch it.

[Matchmaker Maria]

Watch his.

[Jared Freed]

Okay.

[Matchmaker Maria]

Cuz it was such a perfect. I feel like. So when we talk about attitude and like it's like I feel like he did such a perfect like self deprecating joke towards him.

[Jared Freed]

Yeah.

[Matchmaker Maria]

Kind of made everyone feel like, okay, I can relate to this. Right. Like, I think sometimes people go into dating with different attitudes. And you know, for instance, the woman that you, you know, you mentioned just now, her boyfriend might not be aware of what she has consumed or read. So he doesn't know the environment he's dating in.

[Jared Freed]

Well, that, that even more so someone you meet on an app, you don't know, they're coming in with their hot take, hot joke, you know, from a world that allows it. And now you're coming against another person who's in their own algorithm, in their own silo. And they're like, I'm not familiar with that humor. You know, I'm not familiar with that shot you just took at me across the bow, you know?

[Matchmaker Maria]

Yeah. And now. So I've had my business for nearly two decades, so I've been able to. I've had boomers as clients, I've had Gen X.

[Jared Freed]

Sorry to interrupt. I didn't even do this in the. Everyone go follow Matchmaking Maria. You can get, you know, Matchmaking Maria, whether you. The paid unpaid platform, you do it all like she does coaching, you can sign up to be a part of her database where she thinks people up. Matchmaker Maria for single people is like the hub of where you're gonna get like real helpful, like tools as much as you are maybe a match, you know, So I think if they, they need to go follow and she has a great podcast. So go ask a matchmaker. The podcast. Every Wednesday she's taking questions and answering them. Real world, reasonable advice, thoughtful. Matchmaker Maria has been here before, but go follow right now and go listen to her podcast. Okay, so you have every age group.

[Matchmaker Maria]

Yeah. And now we have Gen Z clients.

[Jared Freed]

How is that going?

[Matchmaker Maria]

It's so different. It's so different than for our whole team because it's not just me in the office. I have four senior matchmakers. It's such a different experience. So everything feels like either there's no time, like, oh, my God, I'm 26 and I'm not married yet. Is it over for me?

[Jared Freed]

Right?

[Matchmaker Maria]

Or it's the other extreme where it's like, okay, hey, we have a match for you. You seem really great. I'm so happy we got to meet. I'm so happy at this interview. Let's set it up. When is your availability? This week?

[Jared Freed]

Oo.

[Matchmaker Maria]

This week? Could we wait, like, two months? Do we. Does he. Do they want to have kids? I mean, I don't want to have kids for, like, another 10 years. I don't know.

[Jared Freed]

So is it, like, aloof but on top of it? Like, I. It's weird to be on top of it and reach out to a matchmaker while also being like, oh, not.

[Matchmaker Maria]

And it's both genders.

[Jared Freed]

Yeah.

[Matchmaker Maria]

Like, even my male clients. I have this amazing client right now. I do believe he's going to get married through us. Like, I'm so sure of it. I. If anything, I've ever been sure in my life. He is Indian. He is Muslim. He's currently studying for his residency or, you know, participating in his residency. He's going to be a doctor one day. Well, he is a doctor. Isn't that how it works? He's a doctor. He's a doctor, but he's in residency.

[Jared Freed]

In residency.

[Sponsor/Ad Voice]

That's right.

[Matchmaker Maria]

He's a doctor in residency. So we have been meeting all these incredible matches for him. And, you know, he's been awesome. He's really intentional. And I think most of the women have been also really great, you know, now it's about chemistry, Right? They have to go on the date, see if they like the way each other smell, you know?

[Jared Freed]

Yeah. That's my first move.

[Matchmaker Maria]

It is. I mean.

[Jared Freed]

Okay, nice to meet you.

[Matchmaker Maria]

I really believe you have to like how people smell.

[Jared Freed]

It's all about order. Yeah, we don't. Just don't start with smelling them. I mean, you can get a whiff from.

[Matchmaker Maria]

Do you hug when you go on a first date or do you shake hands?

[Jared Freed]

I. I generally go for a hug. And I. You know what I do on a first date? I go for a hug and I say, good to see you. I don't like to say, good to meet you. And I think a lot of. And I'll have women, they go, nice to meet you, they make a point to say, nice to meet you. I, I kind of go, good to see you. Because we've really met. Like, I'm not like, this isn't. We haven't spoken. We've spoken. I don't know. I always, I, I find it interesting that they.

[Matchmaker Maria]

Do you ask for permission to hug.

[Jared Freed]

Only in a meet and greet line. Generally after a show. I don't, that's. And people ask me permission to hug me. Oh, it goes both ways. So I have people then line, they go, can I hug you? And I absolutely. I'm, I'm gamed. What I appreciate sometimes they're like, I'm a hugger. Get in here. And I'm like, okay. Like, I'm, I'm fine with that. I think they feel they know me in a way, right? On a date, I go for the hug.

[Matchmaker Maria]

So let me tell you what's different about this client, Gen Z. Okay. Because he's had all these conversations with my team about, like, how do you envision the future looking like? And he was telling us about how he'd really like to share his heritage and his faith with his match. So that obviously will narrow the options of who we set him up with. He'll say, you know, here's what I feel like the next three years look like. Here's what I think the next five years look. And we're just talking right now and, you know, what are our hopes and dreams in this experience together? The women we try to. We also have these conversations as well. But it's like their first time going on a date where all of that has already been spoken about ahead of time. It's not this very, you know, cloudy, nebulous, you know, you're going on a.

[Jared Freed]

Date with someone with intention. With intention. The hopes and dreams have been said.

[Matchmaker Maria]

Yeah.

[Jared Freed]

Yeah.

[Matchmaker Maria]

And it's so, hey, you're going out.

[Jared Freed]

With a guy who just said, I am looking be married in the next three years. It's like, yeah.

[Matchmaker Maria]

Especially feedback when they go on dates is so surreal compared to any other generation because first of all, it's so much more fun.

[Jared Freed]

Yeah.

[Matchmaker Maria]

They're thinking, they're like, this is a great date. Here's what I liked about them. I don't know for a long term match because this XYZ doesn't align my future plans and it's not about kids. Like, they're actually thinking in this very, you know, intentional way, which is not unique to me as an elder millennial, because this is how I did. And when I was 28. But it's unique to them because they haven't dated that way.

[Jared Freed]

I think also for, you know, when you're, you know, there in college, like, the idea of us, you know, you and I are the same age. And the idea. There were people that date.

[Matchmaker Maria]

Yeah. To get an Mrs.

[Jared Freed]

Right. That was part of it. That was.

[Matchmaker Maria]

That was a joke.

[Jared Freed]

That was a joke that was going on. But also just, like, the idea of, like, this open idea of casual relationships felt very much their generation.

[Sponsor/Ad Voice]

Yeah.

[Jared Freed]

Like, the idea that. That was to us, I think it was more of a secret. Yeah, it was more. Do you remember when.

[Matchmaker Maria]

Okay, Cupid came out and it was like. Like, I'm taking heroin.

[Jared Freed]

Right. Like, the dating website people are really considered.

[Matchmaker Maria]

Whereas now. Yeah. And then with Gen Z, they're such digital natives.

[Jared Freed]

Yeah.

[Matchmaker Maria]

And they're so incredible about it because they judge you on authenticity. Not. Not no other generation has that as their number one factor. And I'm not saying this like there was a match group study that was conducted to figure out what is Gen Z valuing the most, and it was authenticity, by and large.

[Jared Freed]

Now, speaking of authenticity, that's a good segue to what today we got to talk about. You are dressed ready for Valentine's Day. It is. Look at your shoes. They're wonderful. Everyone go on YouTube. Check out matchmaker Maria shoes.

[Sponsor/Ad Voice]

Oh, God.

[Matchmaker Maria]

This is a workout. These are £50 each.

[Jared Freed]

These are statement makers.

[Podcast Host/Announcer]

These are.

[Jared Freed]

Oh, my God. That chick likes herself some Valentine's Day. If I saw. Like, if I went to an office and there was one woman dressed with these shoes, I would be like, oh, I. Her husband better have done some shit.

[Matchmaker Maria]

Can I just say that the walk over here.

[Jared Freed]

Yeah. You're wearing, like, weighted shoes. Like, it was a moonwalk.

[Matchmaker Maria]

Like, and I don't mean moonwalk like Michael Jackson. I mean, like, Neil Armstrong.

[Jared Freed]

Yeah.

[Matchmaker Maria]

Like, I can't lift my feet now. These are Betsy Johnson.

[Jared Freed]

I think authenticity I like. You know, I wrote some notes for today. Today is Valentine's Day Eve, and I think it's an interesting day because it gets shouted down. Valentine's Day, as you know, we hear from the same people.

[Matchmaker Maria]

This is our third Valentine's Day together in a row.

[Jared Freed]

What do we do? Like, something blue, something new? Do we have. What's the third real. Oh, that you've come on the show.

[Matchmaker Maria]

That you and I spend this week together. Because it was J Train.

[Jared Freed]

Yeah.

[Matchmaker Maria]

Then last year was my podcast.

[Jared Freed]

Yes, yes, yes.

[Matchmaker Maria]

Ask a Matchmaker.

[Jared Freed]

Yeah.

[Matchmaker Maria]

And then this year, it's you up I'm so excited.

[Jared Freed]

This is great. So next year, yearly tradition. We gotta. Well, next year we're gonna do it like, on the Today.

[Matchmaker Maria]

You are literally my most. I don't think I even spend Valentine's Day with my husband because it's such a big media day for me.

[Jared Freed]

Yeah, it's a work.

[Matchmaker Maria]

So for us, it's February 15th, but you are the most consistent Valentine I think I've ever had.

[Jared Freed]

It's great to know. I feel I'm warmed. Well, I. I wanted to bring up Valentine's Day because, you know, you will have people. I will say, as a guy who's like, whatever about Valentine's Day. As a single man, you're single. Single man on Valentine's Day, it's just like, okay. Like, it's like, not a concern.

[Matchmaker Maria]

Yeah.

[Jared Freed]

I'm not, like, at home. I'm not like, get the guys together. Let's have a man, a Valentine's Day. Like, I. There's no societal way for you. It'd be fun to get a bunch of dudes together and do Valentine's Day. You know, go to the bar. I. I've always encouraged men to go to bars on Valentine's Day. I think that tonight's, like, the best.

[Matchmaker Maria]

The dive bars tonight are popping.

[Jared Freed]

Good night to go out. Good night to meet people. Good night to commiserate. Hey, you're single. You know who's single, you know who's not. If they're out on Valentine's Day. Oh, with other women, maybe they're lesbian. Maybe that's their persuasion. But if they're with a big group, you can assume they are single.

[Matchmaker Maria]

Your local watering hole. Today, February 13th, and tomorrow, February 14th.

[Jared Freed]

And it's on the weekend for Friday the 13th. Saturday the 14th. Yeah.

[Matchmaker Maria]

Dude, today and tomorrow are the sluttiest days for single. Like, why Just get off the. You know, don't even think about Valentine's Day. Just know that the people that are coupled up, they're either at home watching some rom com and cooking each other dinner, or they're at a restaurant. They're not at your local dive bar. Right.

[Jared Freed]

They're not dressed down.

[Matchmaker Maria]

No.

[Jared Freed]

You know, they're either dressed all the way down in their PJs or they're dressed up. Lingerie, the middle ground people. You want to be looking for people in jeans tonight. I love this. I actually didn't. You know, I'm. Authenticity. Because that is kind of like the Sesame street magic word. Because when you're out tonight alone, you are single. When you don't do anything for Valentine's Day for someone else. You are single.

[Matchmaker Maria]

Yep.

[Jared Freed]

When something doesn't get done for you or an acknowledgment of the day, if there's no acknowledgment of the day, then there's no acknowledgment of you. So consider yourself single. This is the most authentic. Your partner will be with you. That there's no more authentic day than today.

[Matchmaker Maria]

Yeah. And I think you get to control your narrative. If you. You know, I don't think anyone should feel lonely this weekend. I understand when people do, because maybe you thought that this year you would have a balance. Right. You would have someone to share it with.

[Jared Freed]

No one's telling you to feel lonely. I hope you know, it would be a very extreme case, but I understand it. You're alone on Valentine's Day. Loser. You know, like, that's not gonna happen. That's the movie version of today.

[Matchmaker Maria]

Yeah.

[Jared Freed]

You know, but the reality is, some.

[Matchmaker Maria]

People do feel down.

[Jared Freed]

Of course.

[Matchmaker Maria]

And I just feel like people feel.

[Jared Freed]

Down on a Tuesday.

[Matchmaker Maria]

But you know what? There's also married people who feel down because they're in lonely marriages.

[Jared Freed]

Yeah.

[Matchmaker Maria]

You're not in that.

[Jared Freed]

Right. Well, we could feel lucky for that. Yeah.

[Matchmaker Maria]

Yeah. And that's. I think you get to control the narrative of how this weekend's experience is. You can. You can close the blinds and.

[Jared Freed]

Right.

[Matchmaker Maria]

You know, put on some video games and, you know, order takeout and just not acknowledge anything pink and red.

[Jared Freed]

Right.

[Matchmaker Maria]

You could do that. That's totally fine. Or you can lean in, get yourself to your local watering hole.

[Jared Freed]

Right.

[Matchmaker Maria]

And have a cocktail and chill out.

[Jared Freed]

You know, sit there, have your phone out.

[Matchmaker Maria]

Yeah.

[Jared Freed]

You know, do the crossword. I did the crossword last night at a beautiful bar. I sat out, had the. I was at Chichis. Checchio's. Catchy's. C E, C C H I, O. I went there before I went to the Cellar.

[Matchmaker Maria]

Yeah.

[Jared Freed]

I had. I sat at the bar, took out the crossword and.

[Matchmaker Maria]

Just take out the crossword. On paper or on your phone?

[Jared Freed]

On my phone. I don't like. See, I don't. Chechies. Beautiful bar. I would suggest it highly as far as vibes are concerned.

[Matchmaker Maria]

I feel like you shouldn't do that.

[Jared Freed]

Why not?

[Matchmaker Maria]

It should be on paper.

[Jared Freed]

On paper. That's a. That's like a statement that I'm not looking to make about myself.

[Matchmaker Maria]

Then bring a Kindle.

[Jared Freed]

That's another statement.

[Matchmaker Maria]

Then it just looks like you're like.

[Jared Freed]

Swiping I'm not swiping. I'm. I'm writing.

[Matchmaker Maria]

I know that.

[Jared Freed]

Yeah. I'm saying the paper. I. I think it would be saying to go back to authent.

[Matchmaker Maria]

Yeah, you're doing.

[Jared Freed]

I'm not buying a paper.

[Matchmaker Maria]

You're doing the crossword puzzle because you want to do the crossword puzzle.

[Jared Freed]

Yeah.

[Matchmaker Maria]

And I'm looking at it as, hey, he's doing the crossword puzzle. Why don't you go talk to him?

[Jared Freed]

Right. I. And like, I have the ability to put down the crossroad puzzle, look around the room and go, oh, maybe I could talk to them or, like, have a conversation. But I. I just think it was a nice bar. I just think for this hypothetical person, the watering hole, you know, might be afraid to go alone.

[Matchmaker Maria]

Everyone's there alone.

[Jared Freed]

Yeah. It's fine.

[Matchmaker Maria]

And it's fine. Like, just go by the bar.

[Jared Freed]

What someone say to someone that they want to talk to on Valentine's Day?

[Matchmaker Maria]

What.

[Jared Freed]

What should someone say? What would a good opening line be?

[Matchmaker Maria]

Do you celebrate this holiday?

[Jared Freed]

You go negative.

[Matchmaker Maria]

No, this. I would say, what is the worst dating advice you've heard this year?

[Jared Freed]

The worst dating advice.

[Matchmaker Maria]

And I know the answer already.

[Jared Freed]

What's the answer?

[Matchmaker Maria]

Oh, they told me to go to Home Depot and look confused. Isn't that ridiculous?

[Jared Freed]

Isn't that like, so anti woman I can't stand it. Like, isn't that like, I'm not even sitting here professing myself to be a hero. Like, I'm just. I'm just saying, like, if I don't, like you're telling an adult woman with a college education, go walk into a place and look confused.

[Matchmaker Maria]

Yeah.

[Jared Freed]

So, Maria. What? I have some questions. Before we get into the question today, I have a little bit of a game.

[Sponsor/Ad Voice]

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[Jared Freed]

H-E-L-P.com UUP okay, I'm gonna give you the relationship status. What should happen on Valentine's Day?

[Matchmaker Maria]

Oh, okay.

[Jared Freed]

Okay.

[Matchmaker Maria]

All right. This is a fun game. Okay.

[Jared Freed]

Okay. So meet on an app. They're one month later. They've gone on three dates over the course of a month. Completely normal, Totally normal. Valentine's Day happened. What should anyone do?

[Matchmaker Maria]

You have to acknowledge it for.

[Jared Freed]

Acknowledge the day.

[Matchmaker Maria]

Yeah. But you have to acknowledge it way before, like, February 14th. Like on the 12th.

[Jared Freed]

Okay.

[Matchmaker Maria]

Which is, hey, Valentine's Day is this Saturday. Are we doing something really? And it could be man or woman.

[Jared Freed]

You have to.

[Matchmaker Maria]

I think you should.

[Jared Freed]

You should.

[Matchmaker Maria]

I feel like these holidays, you have any holiday, you have to set up people for. Set them up for success so that they meet whatever expectation you might have in your head.

[Jared Freed]

I would call that person brave and bold. If they had met someone three dates in a month, totally normal. And then they say, hey, Valentine's Day is coming up. I'd love to spend it with you like that.

[Matchmaker Maria]

To me, I didn't say I'd love to spend it with you. I said, are we doing something?

[Jared Freed]

But that's kind of what you're saying, though. I'm not saying there's anything wrong with it. I'm just saying that is bold. That is brave, because you're going to get an answer. You better. Yeah, I think it is.

[Matchmaker Maria]

After three dates, I think it's you.

[Jared Freed]

Saying, I like you and I'm spending and I'm zoning in on you. That doesn't mean anything.

[Matchmaker Maria]

Sounds like a perfect valentine.

[Jared Freed]

It could be if the person's on the same page. If I got that text and I was dating multiple people because I would say as someone who has been three dates in a month in with someone, I'm generally dating other people at that time.

[Matchmaker Maria]

Oh, you do it. You do multiples. You don't do one by one.

[Jared Freed]

Not really. If I'm like on three dates in. If someone else is like, hey, you want to meet my friend? I would go out with a friend.

[Matchmaker Maria]

Sure.

[Sponsor/Ad Voice]

Okay.

[Jared Freed]

But I'm just saying that's, that's. Both are possible.

[Matchmaker Maria]

Right. So you go get them all together.

[Jared Freed]

We all hang out, little bachelor and we see who wins the date, who gets your rose. But I would, I would send the three dates in. You know, maybe this is mean. I'm willing to accept that feedback that like three dates in Happy Valentine's Day while also having gone on a first date with someone that week.

[Matchmaker Maria]

Week. That's fine. You have to text them.

[Jared Freed]

Yeah, I think you have to text them.

[Matchmaker Maria]

Right.

[Jared Freed]

But I think what you're saying is.

[Matchmaker Maria]

You know, it could, you know, listen, you have nothing you could say, do you want to do something? And you could say, yeah, let's go for it doesn't have to be this. You can go for a walk, you know, a Valentine's Day themed coffee from Dunkin Donuts. I'm sure they'll have like heart shaped, you know, donuts.

[Jared Freed]

Yeah, no, I. Okay, so you're one month in, but there's a label. Label.

[Matchmaker Maria]

Oh, that's. That's your Valentine.

[Jared Freed]

Yeah.

[Matchmaker Maria]

Now for sure. It could be dinner, could be sexy sex. Okay. Yeah, there's definitely champagne popping.

[Jared Freed]

Six months label.

[Matchmaker Maria]

How is this a question?

[Jared Freed]

I think there's a lot of people out there. You could be six months in and have no label and just be seeing each other.

[Matchmaker Maria]

Wait, you said six months with label, without label. Oh, that's not. That's nobody. You need to break up with them. Break up with them today.

[Jared Freed]

End it.

[Matchmaker Maria]

End it. You're done. You have three months.

[Jared Freed]

Six months, no label. But there have been dates. No six months, no label, no dates. It's a situation.

[Matchmaker Maria]

Oh, situationship.

[Jared Freed]

Six month situation.

[Matchmaker Maria]

You know what? Six month situationship. That could be your 10:00pm February 14th. You know, you're a little drunk from the bar and you're like, hey, you up?

[Jared Freed]

Okay, let's have a little. Oh, wait, that's the show. One year with a label. What's the, what's the. What's the plan you're making for your significant other?

[Matchmaker Maria]

Dinner, drinks, sexy sex.

[Jared Freed]

Nothing more, nothing less.

[Matchmaker Maria]

Yeah, I don't think you should. I don't think it's funny. Because I got proposed to on February 10th.

[Jared Freed]

Okay.

[Matchmaker Maria]

At. Can I tell you something? Do you know what? Me and my husband have an ongoing. Not fight, but like, our joke to each other for 10 years, 11 years. He proposed to me at a singles event I was hosting.

[Jared Freed]

Okay. In front of everybody.

[Matchmaker Maria]

In front of a bunch of strangers. I don't know.

[Jared Freed]

Yeah.

[Matchmaker Maria]

And he didn't. He neglected to tell someone he was about to propose. I have no photos.

[Jared Freed]

I feel like setting up the camera guy. You know, it's funny, I think, like, from the male side, the straight male side, this stuff gets, like, delivered to you. Like, maybe there's a lag. Like. Like the. The have a photographer thing. Like, my brother had a photographer waiting when he proposed.

[Matchmaker Maria]

Okay. But the irony.

[Jared Freed]

Hiding in the bushes.

[Matchmaker Maria]

But the irony here is that as someone who has gotten, what, 3,000 people engaged at this point? Every day I get a DM of someone's engagement and I have literally over 3,000 photos. Like, that's half of my memory of my iPhone.

[Jared Freed]

But you're the reason.

[Matchmaker Maria]

Those are my rings.

[Jared Freed]

Because of you.

[Matchmaker Maria]

My ring photos.

[Jared Freed]

But that because of you. Those guys know there was no you to tell your guy.

[Matchmaker Maria]

Yeah.

[Jared Freed]

To have the photographer ready, like, make sure the nails are done. Like, these are things I know. With no girlfriend.

[Sponsor/Ad Voice]

Right.

[Jared Freed]

You know, like I'm saying, like, there's a lagging drip of information that gets to the stream.

[Matchmaker Maria]

Was a different time.

[Jared Freed]

All right, let's do the emails. We have some really good emails. These are Valentine's Day, you know, drenched. These are flavored in Valentine's Day themes. We want you to send your emails uup betches.com I also want you to come to a show tonight. Tonight. Tonight I'm going to be in Times Square. Where. That's right, New York City Town hall. I have two shows tonight. I hope by this time they're both sold out. The early one, sold out. But we're taping this early because of the maternity leave of it all. And then I'm going to be in Toronto. I think there might be tickets left there. Toronto, Vancouver, Tempe. Where else? Do I have anything else on that list? I think. Oh, la la la land. Salt Lake City, Utah. Would love to see in Salt Lake City, Utah, at the end of March. Merch jaredfree.com for all the tickets. Watch on YouTube. Subscribe, comment if you're enjoying this show, if you enjoy Matchmaker Maria. And also, most important or not, most importantly, I have more dates coming. But also the book. I have a book. Matchmaker Maria you have a book. Everyone should go buy your book.

[Matchmaker Maria]

Everyone should buy my book. But I read your book.

[Jared Freed]

You read it?

[Matchmaker Maria]

Yeah. I forgot you said the book.

[Jared Freed]

Well, I sent you the book thinking. Because I wanted a blurb from you.

[Matchmaker Maria]

Yeah.

[Jared Freed]

Yeah.

[Matchmaker Maria]

And I actually originally copy pasted the blurb you gave on my book.

[Jared Freed]

Yeah. Yeah.

[Matchmaker Maria]

And I was like, oh, you can use your blurb back.

[Jared Freed]

Yeah.

[Matchmaker Maria]

But no, I was like, oh, no, no, let me read it.

[Jared Freed]

Like, I. I was like, thank you.

[Matchmaker Maria]

You know, it's funny. I really like your book.

[Jared Freed]

Thank you.

[Matchmaker Maria]

Like, I look at the end of the day, you know, you're a comedian.

[Jared Freed]

Yeah.

[Matchmaker Maria]

And I. First of all, I have to say one thing about your book. I'm obsessed with the COVID Thank you. I think the COVID is perfect.

[Jared Freed]

It's the one thing I didn't do.

[Matchmaker Maria]

Can I tell you why I love your cover?

[Jared Freed]

Yeah. Why is that?

[Matchmaker Maria]

Because, first of all, it doesn't look like your typical dating book cover.

[Jared Freed]

Yeah.

[Matchmaker Maria]

But I'm in my mind, I'm like, well, yeah, because Jared is not a dating expert. He is a dater who happens to also be a comedian. So his. His perspective is, first of all, very unique. But also, I feel like this is. When I looked at the COVID I thought, oh, this is a cover of someone's first book.

[Jared Freed]

Yeah.

[Matchmaker Maria]

In the sense that there's going to be more books that come with this and it's going to follow the theme.

[Jared Freed]

I don't know if I could handle it.

[Matchmaker Maria]

I.

[Jared Freed]

It was a tough process.

[Matchmaker Maria]

I'm really proud of you, Z.

[Jared Freed]

Thank you.

[Matchmaker Maria]

And you should totally. Is that what you're about to say?

[Jared Freed]

Yeah. Pre order it. No, thank you. I mean, the goal with the book. And you can say, you can say whether you agree with this, my perspective on the book or whatever, it's first, it's funny. And it's also personal. There's personal stories in there that tell you kind of like what's going on in the mind of me, which is probably what's going on in the mind of a lot of men.

[Matchmaker Maria]

Very validating for any woman to read it.

[Jared Freed]

I think that's what. That's how it's meant to be is, is this, hey, I've had these questions. Why did it go this way? Why did things go down in the way they went down? And I think it's gonna, like, make you feel kind of like those questions could be answered.

[Matchmaker Maria]

I also want to say, and I didn't include this in the blurb, but I do want to say that for a Lot of comedians who have been in that space to write these kinds of books. I feel like you as the writer actually like women.

[Jared Freed]

I hope that shows through.

[Matchmaker Maria]

Look that I.

[Jared Freed]

No, I think like the fear I. I had this kind of. When I would talk about dating, I would always get like.

[Matchmaker Maria]

Like, you respect them is what I'm trying to say. And I. I've read books in the past where, you know, I don't want to mention names, but you know them. And I'm like, I don't think you really. It, like, you. It's almost like a borderline misogyny, right?

[Jared Freed]

No. And they think that they can do it because they're speaking with women.

[Matchmaker Maria]

Right.

[Jared Freed]

And it's like, no, you're kind of speaking at them, like.

[Sponsor/Ad Voice]

Exactly.

[Jared Freed]

And again, I think that's where like a lot listen. I talk about my regrets in dating and like, living and learning. And I think that that's the thing that has to be. There's honest stories. My other. My. My good friend's wife read it and she's like. She was like. He. He was like. She was like, you're going to be like, hearing from people.

[Sponsor/Ad Voice]

Yeah.

[Jared Freed]

Like, you're going to be like, are.

[Matchmaker Maria]

You recording the audiobook?

[Jared Freed]

Yeah, I'm going to do the audiobook. Good.

[Matchmaker Maria]

It's nothing like a podcast.

[Jared Freed]

I know. I can't. I know.

[Matchmaker Maria]

It was as exhausting. You will learn what it's like to be pregnant. That's how. That's what it felt like.

[Jared Freed]

That's what I going to say when. When I have a wife that gets pregnant. I'm going to go, I've done this. I've done this. This is easy. This is. I get it.

[Matchmaker Maria]

It.

[Jared Freed]

All right, let's do some emails. You ready? Dot com. Petty or prudent? So we play this game here on the podcast. You know, you're dating someone, you end it, you do something after it's ended. Have you acted petty or was it prudent? It had needed to be done. J and J and Eminem. I got a petty or prudent for you that I hope gets to you just in time.

[Podcast Host/Announcer]

It did.

[Jared Freed]

I'm 28, female, and I love Valentine's Day. Ever since I was a little girl, my favorite holiday was Valentine's Day. Writing cards, giving flowers to my mom from my siblings, and more.

[Matchmaker Maria]

More.

[Jared Freed]

Call me cliche, but I love a holiday that's centered around showing love and spreading Joy. My boyfriend, 33, is firmly anti Valentine's Day. He thinks it's dumb. Says love shouldn't Be boiled down to one day. He feels like unnecessary pressure fueled by consumerism and that the expectations around gifts and grand gestures make it feel more stressful than meaningful to him.

[Matchmaker Maria]

I can't breathe.

[Jared Freed]

It's like the most exhausting human I've ever met. That fine in theory, but in practice, he won't even say happy Valentine's Day, and it somehow always turns into a fight.

[Matchmaker Maria]

Can I interrupt?

[Jared Freed]

Please?

[Matchmaker Maria]

You know what I would say to this man?

[Jared Freed]

What would you say?

[Matchmaker Maria]

Your mother.

[Jared Freed]

What? You are from New Jersey. Your mother. What do you mean?

[Matchmaker Maria]

This is how he feels about Mother's Day. I'm not gonna text my mom or call my mom and say, happy Mother's Day. I can love my mom any day of the year.

[Jared Freed]

That's a good. That's a good.

[Matchmaker Maria]

Your mother. I am so from New Jersey. God, Microaggression.

[Jared Freed]

No, I think you're right. I think if you wanted to, like, joust with this person, that's a great way to joust with them. I think it's, like, not even worth.

[Matchmaker Maria]

We can keep reading.

[Jared Freed]

Yeah, we keep reading. But I. I think anytime someone tries to bring morality into a discussion, they're no longer discussing, they're now trying to win.

[Matchmaker Maria]

Yeah.

[Jared Freed]

So does he want to discuss or does he want to win? Win. So when you say the consumerism thing, like, that's an eye roll from both of us. We're both sitting here because we've heard that before. That is like the. That's the pull the cord. Because no one can deny that. But when you bring in morality, now I have to bring it to everything you do. Just like Mother's Day, you have to go, well, consumerism. So do you, like, who's to say what's too much consumerism? What's too little? We all consume. So for now, he has to. And he'll never get called out on that. You can't be like, aha, I just bought that V. You know, that. That VCR. I almost went back to 1982. You know, you bought that thing you don't need.

[Matchmaker Maria]

You know, like, I just know a guy like this.

[Jared Freed]

Who you. You know a guy like this?

[Matchmaker Maria]

Yes, I do. You know who they are? I could tell you exactly who they are. Have you ever met a friend who's married with kids and it's Mother's Day, and he does nothing for his wife on Mother's Day?

[Jared Freed]

Yeah.

[Matchmaker Maria]

Yeah, that's the guy.

[Jared Freed]

That's a similar. Well, they're doing the morality play.

[Sponsor/Ad Voice]

Play.

[Jared Freed]

She's not my mother. That's What? That. I mean, that's okay.

[Matchmaker Maria]

I'm sorry. Your child is four.

[Jared Freed]

I'm just saying. That's the eye roll. That's them using the technicality. The small in the small. I'm not agreeing with them. You're looking at me like I'm agreeing with them.

[Matchmaker Maria]

I'm saying, no, just call them a piece of.

[Jared Freed]

Yeah, they're a piece of. But I'm saying that's like the move. Like.

[Matchmaker Maria]

Yeah, that's the moment move.

[Jared Freed]

I think anytime you go, you. Anytime you go. Well, I'm not. They're not my mother.

[Matchmaker Maria]

You.

[Jared Freed]

Anytime you go to the small writing to make someone feel bad. Dad, you're not engaging with them. Like, this woman, whether she loved Valentine's Day or Furies, it wouldn't matter. She loves it. It's your. It's your girlfriend. So are you gonna tell her she's stupid for liking Furbies, or are you gonna go? This is the woman I've signed up for with Furby, and Without fur, she's.

[Matchmaker Maria]

28, so I don't know if she knows what a Furby is.

[Jared Freed]

Just.

[Podcast Host/Announcer]

I'm.

[Matchmaker Maria]

I'm trying to connect to you, but I wanna. I wanna.

[Sponsor/Ad Voice]

What?

[Matchmaker Maria]

I. I. First of all, I 100 agree with you. And I think that comes down to the. And we haven't even read the whole question, but this is the answer, which is the moment one of you likes it, you have to celebrate it, right? That's it. Like.

[Jared Freed]

Or at least acknowledge it, like in your own way. Like one day here. To me, it's like such a nothing thing, but. Okay, we'll keep going.

[Matchmaker Maria]

All right.

[Jared Freed]

This will be our third Valentine's Day together, just like us. And I finally decided that if my man refuses to do things, things I want on Valentine's Day, I'll do them myself.

[Matchmaker Maria]

Queen.

[Jared Freed]

Last year, we received a gift card from friends to a very bougie spa in town. They specifically said it was for us and that there was enough on it for a couple's massage. We've never used it. After our most recent Valentine's Day fight, I booked myself a massage, facial, pedicure using the whole gift card. The next week, when we were talking about our plans for weekend Valentine's Day weekend, I mentioned that I was busy Saturday treating myself at the spa. And time down, he asked what I meant and when I told him, he did a double take and said, did you use some of the credit we were saving for a special occasion?

[Matchmaker Maria]

Saving? It was a gift.

[Jared Freed]

I said I used it all. It's Valentine's Day. And since you're protesting something so small, I'm letting you technically treat me anyway. He's upset because he was looking forward to enjoying the spa together. I told him he had 364 other days to plan that and to pay for it.

[Sponsor/Ad Voice]

It.

[Jared Freed]

Well, they had the gift card.

[Matchmaker Maria]

Yeah, yeah. I'm saying he can plan another one and pay for it.

[Jared Freed]

He could if he wanted to. And if Valentine's Day was too stupid to acknowledge, then I'd happily go solo and enjoy every minute. So petty or prudent? If your boyfriend protests Valentine's Day so hard, is it fair to celebrate yourself? Even if it means there will be no shared spa day? Gifting yourself the entire shared gift. Thanks. A soon to be well moisturized batch. What do you think? Is it petty or prudent?

[Matchmaker Maria]

I mean, it's petty, but I don't think that's a bad thing.

[Jared Freed]

Okay.

[Matchmaker Maria]

Like, she could have had that spa day.

[Jared Freed]

Yeah.

[Matchmaker Maria]

Any other day as well. By herself.

[Jared Freed]

Right.

[Matchmaker Maria]

Like, you know, you shouldn't have to wait for a holiday to give yourself happy treatment.

[Jared Freed]

Right.

[Sponsor/Ad Voice]

Right.

[Matchmaker Maria]

And like, wellness. She's petty because she chose that specific day. And, you know, look at the day. Healthy relationships.

[Jared Freed]

Would you call this a healthy relationship?

[Matchmaker Maria]

No. No, because healthy relationships are dependent on these bids to connect.

[Jared Freed]

Right.

[Matchmaker Maria]

And you need lots of happy, positive bids. Like, you know, and what I mean by that is being able to acknowledge each other, being able to respect each other. And instead of telling them ahead of time, hey, since you don't want to celebrate Valentine's Day, I've decided I really want to celebrate Valentine's Day. So I'm going to use that gift card that was gifted to both of us on myself that day. How do you feel about that? And he could have said, you know what? I don't usually celebrate Valentine's Day, but I would love to do that on Saturday with you do. Let's do it together.

[Jared Freed]

I. That's the healthiest way this could have gone. What you just said is exactly correct.

[Guest/Additional Host]

And.

[Jared Freed]

And it's the way everyone puts down their knives. Like, that's the way everyone puts. Puts their gun on the.

[Matchmaker Maria]

You either want to be right or you want to be happy.

[Jared Freed]

That's the point is like, he, He.

[Sponsor/Ad Voice]

If.

[Jared Freed]

If it acted out that way, she would be so, like, happy, enthused. And if she wasn't and wrote into us, can you believe it took me to do that? We go, you're asking for too much. You're trying to push a string. You Got what you want. He saw the error of his ways. He saw an opportunity to appease you on a day that you liked. It did take you making a move, but you got there. Let's. Let's be happy.

[Matchmaker Maria]

And then it becomes an annual tradition.

[Jared Freed]

Right. How this is the way we do it. And now you don't. You like it? And you go, I do like it. I. But I think in this scenario, she's being petty.

[Podcast Host/Announcer]

I agree.

[Jared Freed]

If I'm, if I'm forced to give an answer, it's your game. Of course I'm forcing myself to give an answer. It's petty. I, I, I think petty. Matching petty. Because he's petty too.

[Matchmaker Maria]

Yeah.

[Jared Freed]

His, his inability to, like, budge on Valentine's Day is a petty maneuver. To say it's about consumerism is literally the definition of petty to me.

[Matchmaker Maria]

Like, to be like, every holiday is consumerism.

[Jared Freed]

Right. Everything is consumerism in a certain way. You know, that's like saying, you know, oh, you use a phone, it's made by little kids. And then just making someone have to deal with that. Like, you, like, there's a huge issue in this relationship.

[Matchmaker Maria]

Yeah.

[Jared Freed]

Like, whether she wants to admit it or not. Not like, this is three years. Three years. And he won't even. Like, you're having the same fight about Valentine's Day, about. And then consumerism is brought up.

[Matchmaker Maria]

She also sucks, too. I don't want. I'm not. Dear listener, I say this respectfully. You've outgrown this relationship, and instead you're doing stuff like this instead of just, you know, participating in a relationship and compromising and learning how to work together where your needs are met and his needs are met.

[Jared Freed]

She's caught up on this game that she's not admitting isn't a game game.

[Sponsor/Ad Voice]

Yeah.

[Jared Freed]

Like, the whole Valentine's Day, she's like, there's some people that have these arguments, and they go, well, it's about Valentine's Day. We are sitting here going, no, it's not. Here's the thing. I'll be personal about a Saturday.

[Matchmaker Maria]

Right?

[Jared Freed]

This is about a Saturday. This is about how you bend for your partner. I'll be personal. There have been relationships I have bowed out of because I'm like, if I'm not excited to do this thing, I'd rather not be in a thing. And I think what this guy's doing is he's trying to have his cake and eat it, too. He's like, like, no, I'm gonna not budge on this one thing that is really important. To my. The way she wrote it. Based on what she wrote, I am gonna do this. Ever since a kid, I've been Valentine's Day my whole life. And he's like, he won't budge here. Then why is he in a relationship? Because he feels lonely.

[Matchmaker Maria]

Right.

[Jared Freed]

So it's like he's having it all.

[Matchmaker Maria]

Right.

[Jared Freed]

And he's dealing with a fight every year where he ends up winning.

[Matchmaker Maria]

Can I ask you a personal question? It's about sex.

[Jared Freed]

Sex, sure.

[Matchmaker Maria]

Do you like. First off, do you like.

[Jared Freed]

Yes, I do. Like a blonde.

[Matchmaker Maria]

Do you like lingerie?

[Jared Freed]

I. I kind of.

[Matchmaker Maria]

Okay.

[Jared Freed]

I. I go lingerie. It's nice that they feel sexy. I like that they're more confident.

[Matchmaker Maria]

Yeah, perfect answer.

[Jared Freed]

Okay.

[Matchmaker Maria]

Wow.

[Jared Freed]

I nailed it.

[Matchmaker Maria]

Wow. Nailed it. Okay, so you know how around this time, lingerie being sold in, like, red and pink? I always wonder about the people who don't like to celebrate Valentine's Day. It's like, so if your girlfriend showed up wearing, like. Like, a red lacy number, you should be like, this is too consumerism. Put on the black number.

[Jared Freed]

Right. Of you crazy. Yeah. I don't know.

[Matchmaker Maria]

Like, where does the consumerism line end?

[Jared Freed]

That's my point about bringing up morality in an argument.

[Matchmaker Maria]

Because you gave such a good answer, it's like, what a safe answer.

[Jared Freed]

What do you mean? Is it safe?

[Matchmaker Maria]

Yeah, like, I love that you made it about her. Like, well, if you look, you feel good.

[Jared Freed]

I'm just saying. Well, listen, I just think Lingre has been over I. Considering how much porn is out there.

[Matchmaker Maria]

Yeah, it's, like, sensitive.

[Jared Freed]

We're just sensitive. Like, maybe at one point that was, like, a thing. Yeah, I do. I mean, I want in a sexual situation for a woman to have, like, to be, like, bold and. And, like, a little bit outside of herself. And I think sometimes lingerie can put you in that mood. Like, that would be my preference. Yeah, lingerie. But now we know that now that we've gotten personal. Buy the lingerie later.

[Sponsor/Ad Voice]

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[Guest/Additional Host]

Dearest gentle reader, this is Lady Alison Hammond, host of the official Bridgerton Podcast. I'll be sitting down for high tea and fancy bonbons with my favorite members of the Bridgerton cast like Luke Thompson and Yerin Ha, AKA Benedict and Sophie, Claudia, Jessie and Hannah Dodd, who play our beloved Bridgerton sisters Eloise and Francesca. I'll even be holding court with Queen Charlotte herself, Golda Rocha, Val and Mama Bridgerton Ruth Gemmel. I'll also be checking to some of the brilliant minds who bring the ton to life, such as showrunner Jess Brownau and TV legend Shonda Rhimes. You'll be able to watch our video episodes on Netflix right away. Meanwhile, audio episodes will debut weekly on Spotify, Apple and wherever you get your podcasts. So gentle reader, don your finest attire and ready your heart for the official Bridgerton Podcast.

[Matchmaker Maria]

If the Featherington carriage is a rocking.

[Jared Freed]

Do not go a knocking.

[Guest/Additional Host]

It's a gala ball and you're all invited ta.

[Jared Freed]

Oh, could this vintage store be any cuter?

[Sponsor/Ad Voice]

Right?

[Matchmaker Maria]

And the best part? They accept Discover. Except Discover in a little place like this? I don't think so.

[Sponsor/Ad Voice]

Jennifer.

[Guest/Additional Host]

Oh yeah, huh.

[Matchmaker Maria]

Discover is accepted where I like to shop. Come on baby, get with the time times.

[Jared Freed]

Right, so we shouldn't get the parachute pants.

[Matchmaker Maria]

These are making a comeback, I think.

[Jared Freed]

Discover is accepted at 99 of places that take credit cards nationwide, based on the February 2025 Nielsen report. So let's do an email. You ready? Uuppages.com magic and Ria, I. I'm gonna let you read the email. I'll let you do the honors.

[Matchmaker Maria]

All right. Hey, J. And J and Eminem. I love that, by the way.

[Jared Freed]

Yeah, we. We get you involved.

[Matchmaker Maria]

Involved. Love the pod and loving the latest benefits episode. Congratulations, Jordana.

[Jared Freed]

Oh, thank. I'll take the. Thank you. I'll give you. Thank you.

[Matchmaker Maria]

I have a question that I need some insight on and how to say no and how to keep dating. I, 24, have been dating this guy, 27, since the beginning of the year. Let's call him T. T and I have had really awesome dates. Fun cocktail bars, movie nights, and we even went to see Jared at the comedy seller. Jared, you're so hilarious.

[Jared Freed]

Thank you.

[Matchmaker Maria]

I've learned a lot about tea the last seven dates, and I feel we align in a lot of ways and values. Now, these dates always end in heavy makeouts. I love that.

[Jared Freed]

Love a heavy makeup. And I know he love an hmo.

[Matchmaker Maria]

Yeah.

[Jared Freed]

Stupid.

[Matchmaker Maria]

It's funny.

[Jared Freed]

You should be a comedian. Thank you. Matchmaker is going to talk about HMOs and how they're praying off the weak and. And we're going to go in a health care discussion, but. Okay, go ahead.

[Matchmaker Maria]

All right. I know he wants to go further, but I want to take things slow. I haven't dated much, and after you had Matchmaker Marie on the podcast, this is so meta. I Learned about her 12 date rule, and I felt that it really resonated with me. I want to wait 12 days to have sex with T. For sure. Now for my question, T started asking about Valentine's Day and that he wants. Wants to have me over for dinner, cook for me, and have wine. I can't help that he's going to want more. Of course. I really don't know how to communicate with him that I'm attracted to him. But we should wait to have sex after a few dates. I don't want to be a mood killer and think that I'm not attracted to him. I know that is the point of the rule, but I think I need help with language that isn't just snow and ruin our first Valentine's together. What do you think? How do I tell the guy I want to wait? Oh, my God, I have so many thoughts. Thoughts.

[Jared Freed]

Well, give us some.

[Matchmaker Maria]

So for anyone who's a new listener or a new watcher, if you're watching this on YouTube, and if you are watching this on YouTube, don't forget to leave a comment and say hi. I do monitor the comments.

[Jared Freed]

We read it all I do.

[Matchmaker Maria]

Oh, I like it.

[Jared Freed]

Yeah, it's fun, it's cute.

[Matchmaker Maria]

I like to be on the understand.

[Jared Freed]

Well, I like to hear what people like. I like to hear what people laughed at. Oh my God. This part is. I'm dying. Like that's always great.

[Matchmaker Maria]

Yeah. Hmo.

[Jared Freed]

Hmo.

[Matchmaker Maria]

All right, so if this is your first introduction to me. Hi. I came up with the 12 date rule method. And it's a really popular method for people to discover if they are compatible with someone from an emotional perspective without the distraction of physical intimacy. That's not to say that you can't do other stuff. And that's all. There's also this like matchmaker Maria math. So the first a date counts if it's a minimum of 20 minutes, maximum three hours. And it could be a phone call, a video date or an in person date. And three of the 12 must be in person. So reading this, I'm kind of looking at the math. She has had seven dates. There has had to been phone calls or video calls between these two dates. Especially since what, January, like in six weeks.

[Jared Freed]

Right.

[Matchmaker Maria]

Typically the 12 date rule historically is completed if you're still at 12. Like if you actually get to 12. Cuz the point is to not get to 12 with everybody. It's to break up with them.

[Jared Freed]

Yeah. Or they break up with you.

[Matchmaker Maria]

Oh right. For sure. It takes about two and a half, three weeks.

[Jared Freed]

Okay.

[Matchmaker Maria]

Okay. So we're already. I feel like she's way past the 12 date. I don't want someone using this method as an excuse to say like well I'm not attracted to him either. Like if you're not attracted to them, you should break up with them at this point.

[Jared Freed]

Right. Well I guess that would be the problem if I were you, you know, and someone was like I use the 12 day rule and I guess I have to them now.

[Matchmaker Maria]

Yeah.

[Jared Freed]

Like you're like you've kind of misinterpreted the rule.

[Matchmaker Maria]

Right?

[Jared Freed]

What I would. And that would frustrate me because it's like I don't know if I can explain it better than I did.

[Sponsor/Ad Voice]

Right.

[Jared Freed]

You know, like because what you're saying, 12 dates, you're basically saying get that out of your head. Now you have one less thing to worry about.

[Sponsor/Ad Voice]

Right.

[Jared Freed]

Since you've already decided that I don't get to that level of intimacy until 12 dates. This is my understanding, the rule. Maybe I'm wrong that you get it out of your head so that you can concentrate on all the other things.

[Matchmaker Maria]

How do they treat you?

[Jared Freed]

How they treat you whether they like you. And then what you're saying to the other person is, they, you, you're. Without saying it, you're saying you gotta do some work here.

[Matchmaker Maria]

If they miss that mark, you might not get 212. You're like, okay, it's been eight dates according to matchmaker Maria Math. Maybe those were two physical dates and like, you know, four Zooms or whatever. I'm not feeling it. I gotta break up.

[Jared Freed]

Right? Well that, that's the whole point that sometimes I would assume people miss.

[Sponsor/Ad Voice]

Yeah.

[Jared Freed]

This isn't something you have to get to.

[Sponsor/Ad Voice]

Right.

[Jared Freed]

This is something to help you kind of like judge it out.

[Matchmaker Maria]

Yeah. And I also. It's okay to tell someone. Forget the 12D rule for a second. It's okay to tell someone. I would love to spend bal Valentine's Day with you. I think coming over your house sounds like a really great and intimate idea. Let's see. Let's have a makeout session. Like you can say no. Like if you're scared that they're going to be upset that you don't want to have sex, you shouldn't be going over their house if you don't trust that they can handle their emotions.

[Jared Freed]

Like, this is like, let me give a. Well, let me give a more normal other side of the equation. The other side of the equation. If someone said to me, hey, hey, I've been having a lot of fun, I want to come over for dinner. I'm just letting you know, like we are moving towards like something here. I'm getting to know you. I'm having a great time. I'm just making sure I let you know before I come over. Like the level of intimacy probably not going to like grow isn't going to happen. Like I don't want to be in a scenario where you think something's going to happen that won't happen. I'm just letting you know I'm coming over to have fun, but I'm not going to sleep over. I'm not looking for that. That yet.

[Matchmaker Maria]

Okay.

[Jared Freed]

If so. Cuz that seems like a normal.

[Matchmaker Maria]

If you heard that as a man.

[Jared Freed]

If I heard that as a man, it would be to like, if I was like into this person and dating them, I would go, that's no problem. Of course, yeah, I'm excited for you to come over. Come over. I'm cooking dinner. That's not even on my mind. It's on my mind, but it's not. That's not even like, okay, I'll take it off the table.

[Matchmaker Maria]

Right.

[Jared Freed]

If I didn't want, if I didn't see a few, now it's forcing me. And I think this is like the power of the 12 day rule and this is forcing me. Jared, who might not think he needs the 12 dates to be intimate.

[Matchmaker Maria]

No man does.

[Jared Freed]

Well, I'm being kind by saying, that's me. That's me. Yeah, okay. I would go, okay, well now that this person's looking at me seriously and I need to make sure that if I have them over, I'm taking this seriously. Yeah, it makes me zone in. So that's like a normal human response. Not, not what the. I don't think, I think that's an extreme version of a person to go, well, if you're not me, don't come over. Like, I don't think that's what's, I think what's going to happen is you're letting the guy know I'm going to, I'm taking this seriously. He, I think most people don't want to be bad people. They go, oh, okay, okay, sounds good. That's the page you're on. I better catch up to that page or I better end this.

[Matchmaker Maria]

I mean, I just don't see the difference between her saying, you know, whatever you just said, I think is great.

[Jared Freed]

Yeah.

[Matchmaker Maria]

But also she could also be ready and she's like, oh, I have my period. I don't like having sex on my period.

[Jared Freed]

She could do that.

[Matchmaker Maria]

And what's he going to do?

[Sponsor/Ad Voice]

Cry?

[Jared Freed]

Like, you know, I would say again.

[Matchmaker Maria]

I think in here's a few more chocolates. You know, I don't know.

[Jared Freed]

Right. Well, I mean, but I think in normal dating the guy goes, oh yeah, totally. I guess like you would hope again again. Like sometimes we're forced to like other.

[Matchmaker Maria]

Reaction other than, yeah, okay, right. You don't date that man. The 12 day rule worked.

[Jared Freed]

Right.

[Matchmaker Maria]

You're not dating the wrong person.

[Jared Freed]

Or you know, don't date that guy. But also like be awake. Listen, you know, like I, I, there's a little self responsibility there. Someone can go, oh, well, he reacted bad. Like, you know, we, he have these emails, this woman with the Valentine's Day, well, we get in a fight about Valentine's Day every year. It's like, listen, yeah, there's a fight here that's real, you know, so like, like you, you know, the 12 day rule isn't meant to like make it so you don't have critical thought.

[Matchmaker Maria]

I, I also tell people, like, just because you got the 12, if you're not ready, you don't have sex. And also, if that opportunity doesn't come up, you don't have sex. I think for me, my husband was like, 16 dates in, like, just because we didn't have time. We were never alone to do that, you know?

[Jared Freed]

And I will say also, men don't count as much as women in the beginning.

[Matchmaker Maria]

Yeah.

[Jared Freed]

You know, they. We don't do that. Just generally, like, when a woman.

[Matchmaker Maria]

I didn't tell my husband I was doing this to him. Sure.

[Jared Freed]

You as. Who cares?

[Matchmaker Maria]

Like, I'll tell you when I'm ready.

[Jared Freed]

Right. I'm just not there yet.

[Matchmaker Maria]

I'm not there yet.

[Jared Freed]

That's always the explanation you need.

[Matchmaker Maria]

But I'm saying I'm really good in bed, though.

[Jared Freed]

They go three.

[Matchmaker Maria]

I did say that.

[Jared Freed]

Just so you know, when it happens, you will be wowed.

[Matchmaker Maria]

I said that to him. I said, I'm not. That is exact. Put a Greek accent on it.

[Jared Freed]

Yo, yo, yo, yo, yo, yo, yo. Is that the Greek version?

[Matchmaker Maria]

Perfect, Perfect. No, that's. Yeah. I said to him, I really love getting to know you. I really like love. I really like getting to know you. I. You know, when I'm ready to take it to that level, I'm gonna let you know, I like you. I'm great in bed. I got rid of all the hesitations, like, oh, maybe she doesn't like me, or maybe she's a prude or whatever, you know?

[Jared Freed]

Like. Right.

[Matchmaker Maria]

And then there was it. We just moved on. I did not do this naked. I did not do this at home. I did this while we were walking, like, on the sidewalk.

[Jared Freed]

Okay.

[Matchmaker Maria]

Somewhere in Chelsea, as one does.

[Jared Freed]

That's like the speech that Liam Neeson gives to Pamela Anderson. No. Over the phone. That he gives to the taken guy. I have a very special set of skills. They will not happen tonight, but they will happen in the future if you do the right thing.

[Matchmaker Maria]

Yeah. My husband used that monologue to ask me out on a third date. I'm not kidding.

[Jared Freed]

I have a special set of skills. If you've.

[Matchmaker Maria]

Yeah, I have. I have the letter where he wrote it on a letter.

[Jared Freed]

A letter. Matchmaker Maria, thank you for coming on. We solved dating.

[Matchmaker Maria]

We did. We're done.

[Jared Freed]

Everyone go follow Matchmaker Maria Ask a Matchmaker podcast. Go. Listen, go subscribe. Also, Matchmaker Maria's book. Go, go, go. Ask a matchmaker that. It's all name the same thing. So these are all easy things to find on Spotify. It's on Spotify.

[Matchmaker Maria]

Did you know that Spotify has audiobooks.

[Jared Freed]

I didn't know that.

[Matchmaker Maria]

Yeah, I mean, so while you're on Spotify, you subscribe to Badges, you subscribe to Ask a Matchmaker podcast, you pre order Jared's audiobook, you purchase my audiobook, you can have the true parasocial relationship you deserve.

[Jared Freed]

That's right. So we'll be back next week. Happy Valentine's Day. Boom.

[Matchmaker Maria]

Happy Valentine's Day.

[Podcast Host/Announcer]

Thanks again to Courier on Uber for sponsoring this episode. Whether you're looking to send a Valentine's surprise, a homemade treat or something else meaningful across town, Courier can help deliver it. Courier is an on demand delivery service inside the Uber app that helps deliver what you already have stress free, like forgotten items, package returns or that niche gift you left at home that says I really know you because when love gets busy, there's courier. Just open the Uber app, slide over to the Courier tab, select your delivery type and let Courier help deliver what matters.