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

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.

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)

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)

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)

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

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)

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.

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.