U Up? Podcast Episode Summary

Episode Title: 30 Taylor Swift Shows Later… Red Flag?

Date: October 1, 2025
Hosts: Jordana Abraham & Jared Freid

Main Theme / Overview

In this lively, banter-filled episode, Jordana and Jared tackle a variety of questions and scenarios about modern dating—everything from funny anecdotes about hotel upgrades to whether attending 30 Taylor Swift concerts is a red flag. The episode explores topics like dealbreakers, nuanced red flags, profile honesty, food quirks, and the complexities of dating app interactions, all through the signature comedic and honest lens that defines “U Up?”. The hosts provide personal stories, listener advice, and plenty of memorable asides on dating standards, boundaries, and the ever-present role of technology in relationships.

Key Discussion Points & Insights

1. NYC Hotel Adventure & The Power of Serendipity

• [03:01-10:50] Jared shares his recent hotel drama: after being priced out of his NYC hotel, a random encounter with the GM of Moxie hotel (who thought he was someone named Josh) landed him a heavily discounted room.
  • "That should be illegal, right?" — Jordana [04:29]
  • Casts light on how odd connections and luck can benefit you, even if they stem from misunderstandings.
  • Both hosts joke about fan encounters and the New York lifestyle ("You support me and the thing I care about the most. You can call me Patty, I don't give a—" — Jared [11:14]).

2. Nostalgia & Dating Analogies

• [13:02-14:43] Conversation about the movie “You’ve Got Mail” and the rising costs of NYC life turns into a reflection on time, dating, and youth.
  • "Like, a decaf grande macchiato is now like 8.50, probably." — Jordana [13:38]
  • This chat mirrors the dating world: the past always feels closer than it is, and perceptions change with time.

3. The Taylor Swift 30-Concert Dilemma: Red Flag or Dealbreaker?

• [14:46-16:12] The hosts present the main topic: Is attending 30 Taylor Swift concerts a relationship red flag?
  • Both agree it’s less about Taylor Swift, more about obsession: “Anyone who goes to 30 concerts of one band... that’s a groupie.” — Jared [15:43]
  • Jordana: “I want to say I don't think it's a dealbreaker, but it is a red flag.” [15:37]
  • They note that this signals a deeper identity issue—dating someone with such a dominating hobby means signing up for their whole world.
  • Memorable Moment: “Unless they’ve been to 30 J Train standup shows... even for you, you lose it.” — Jordana [16:18]

4. Dating Profile Dilemmas—Clarifying Desires About Kids

• [27:00-36:59] A listener asks for advice: she doesn’t want kids, but keeps getting likes from men who do.
  • Jordana hypothesizes men often swipe for “hotness” over substance: “Men are on these apps... open, let’s see, who knows?" — Jared [30:02]
  • Both agree: It’s fine to filter aggressively; do not feel guilt.
  • Jared highlights the open-endedness of many men’s intentions ("The penis does the picking” — Jordana [35:28]).
  • Advice: If it’s a dealbreaker for you, treat it as such. Talk about these issues early!
  • Discussion concludes that apps allow unprecedented control in filtering for true compatibility.

5. Icky or Picky: The Chef Who Eats Only PB&Js

• [37:01-39:38] A woman is weirded out that her chef boyfriend almost exclusively eats PB&Js.
  • Hosts find her criticism more off-putting than his eating habits.
  • Jordana: “If I'm a chef, I could totally see wanting to come home and be like, I want something extremely simple.” [39:07]
  • Jared sympathizes: doing a creative or physical job can foster a desire for simple routines.
  • Both agree: trying to force a habit change this early on is a red flag from the complainer, not the chef.
  • Memorable Quote: “I’d dump her immediately.” — Jared [38:50]

6. Red Flag or Dealbreaker Games

• Key Scenarios & Opinions:
  • Bringing Your Own Food to a Ball Game ([57:20-64:38])
    • Scenario: A date brings their own sandwich to a game but doesn’t offer to bring any for their companion.
    • Both find it icky and a dealbreaker—basic consideration is expected.
    • "It is ballsy to eat two sandwiches in front of someone and not offer them one." — Jordana [64:22]
  • Secret Finsta Account ([64:40-69:14])
    • A listener finds out his girlfriend has a private Instagram account she won’t let him see.
    • Both lean toward red flag—less about privacy, more about maturity and transparency: "If you can't look at your partner and go, 'Yeah, it's so embarrassing,' and then show them..." — Jared [67:48]
  • Public Following of “Softcore” Accounts ([73:02-84:47])
    • Questions about a boyfriend who publicly follows an influencer with revealing photos.
    • Jordana and Jared agree: It’s not the content, it’s the public nature and “why bother?” that make it questionable.
    • "If you're in a relationship, why do you need to like this? That's unnecessary." — Jordana [83:13]
    • Advice: It's okay to ask for discretion or private consumption if it makes you uncomfortable.

7. Confessing Feelings to a Friend—Honesty Rejection Debrief

• [45:05-54:58] Listener update: she confessed her feelings to a male friend and was gently but firmly turned down (he gave multiple vague excuses).
  • Jared: “He’s not going to date you. You need to move on.” [50:55]
  • Jordana applauds the courage, noting you win by getting clarity—even if you don't get the outcome you want.

Notable Quotes & Moments (with Timestamps)

• On luck and mistaken identity:
  "You support me and the thing that I care about the most. You can call me Patty, I don't give a—" — Jared [11:14]
• Red flag for groupies:
  "Anyone who goes to 30 concerts of one band... that’s a groupie." — Jared [15:43]
• PB&J debate:
  "I’d dump her immediately." — Jared [38:50]
• On dating apps:
  “Men are on these apps... open, let’s see, who knows?" — Jared [30:02]
• On why you should filter aggressively:
  "Like, who has ever had that ability in the history of dating to be like, I don't want to see your f**ing face if you don't like this one thing..."* — Jordana [33:42]
• On relationship transparency:
  “If you can't look at your partner and go, ‘Yeah, it's so embarrassing,’ and then show them..." — Jared [67:48]

Major Takeaways & Listener Advice

• Be clear about your dealbreakers (especially serious things like kids).
• Don't overthink how others might judge your preferences—apps allow you to filter for yourself, not your friends.
• Obsession in any form—whether music fandom or dietary habits—should prompt deeper questions about lifestyle compatibility.
• A little weirdness is OK, but lack of basic consideration (like not offering to share a sandwich) isn't.
• Bravery in expressing feelings is admirable, even if it ends in rejection.
• Privacy in a relationship is okay, but complete secrecy often signals deeper immaturity or disconnect.
• Everyone has quirks online (old Finstas, followers), but it's how openly they're addressed with a partner that matters.

Additional Notes & Final Thoughts

• The episode is packed with the hosts' trademark humor, sarcasm, and open acknowledgment of their biases.
• Listeners are encouraged to write in with their own red flag/dealbreaker scenarios, relationship questions, and feedback.
• Several in-pod promotions for the “U Up? with Benefits” subscription content and bonus podcast segments.
• The show ends with reminders to catch bonus episodes, submit questions, and the classic—“We did it! Solve dat(ing)!” [85:25]

Timestamps for Key Segments

• 03:01-10:50 — Jared’s Moxie hotel story
• 14:46-16:12 — Taylor Swift concert red flag
• 27:00-36:59 — Dating apps and children discussion
• 37:01-39:38 — PB&J chef: Icky or picky?
• 45:05-54:58 — Confessing feelings to a friend (listener story)
• 57:20-64:38 — Red Flag Game (Baseball game date food scenario)
• 64:40-69:14 — Secret Finsta account in relationships
• 73:02-84:47 — Public following of “softcore” accounts while in a relationship

For Listeners Who Haven’t Tuned In:

This episode delivers relatable dating scenarios, textured advice, and plenty of laughs—essential listening for anyone navigating the modern dating world with an eye for honesty, boundaries, and a good story.