U Up? Podcast – Episode Summary

Episode Title: How to Date Your Roommate
Date: September 24, 2025
Hosts: Jordana Abraham & Jared Freid
Podcast: U Up? by Betches Media

Brief Overview

In this episode, Jordana and Jared dive into the complexities of living and dating in the modern world—from funny personal stories and pop culture tangents to thought-provoking listener dilemmas. The central theme explores the awkward reality of falling for a roommate, the boundaries of friendship versus romance, and the often-messy navigation of housemate hookups. The pair also field listener questions about dating app mishaps, communication styles, red flags, and “icky or picky” scenarios, all colored with their characteristic mix of sharp humor and genuine empathy.

Key Discussion Points & Insights

1. Catching Up: Birthdays, McFingers & Vanity Plates

• Birthday Recap: Jordana shares details of her birthday, following Jared’s “birthday routine” of self-care and relaxation, complete with a 90-minute home massage.
  • “There's only so many times you can poop in all the bathrooms of the house.” – Jared (02:26)
• Meet ‘McFingers’: Jordana describes her quirky masseuse, Mary Jo, with pink hair and a license plate reading “McFingers,” spurring a hilarious sidebar on inappropriate vanity plate possibilities (05:17).
  • “If only a woman could be McFingers... if she was a man McFinger, you'd have a restraining order.” – Jared (05:42)
• Vanity Plate Brainstorming: The hosts suggest possible plates for Jared, riffing on old sports nicknames like “TD Freed,” and sharing their embarrassing AIM screen names from their youth.
  • “Fat Athletes of America Forever. That was my AOL screen name.” – Jared (09:44)
  • “Curl Girl 97, because I had curly hair... Not, like, playground curls!” – Jordana (10:16)

2. Travel Tales: Winnipeg, Providence, and Gifts with Genitals

• Winnipeg Adventures: Jared recounts visiting Winnipeg, golfing with a fan’s husband, and being delightfully surprised by Canadian hospitality and humility.
  • “No one would ever do their bachelorette party in Winnipeg… You would if you lived there.” – Jared (17:58)
• Souvenirs & Studio Decor: Between listener gifts and staff travels, the studio adds a Winnipeg Jets shot glass and an Italian espresso cup adorned with a statue of David’s phallus—garnering raucous commentary.
  • “No matter where in the world you go you can find an oddly placed genital gift.” – Jared (24:38)
• Jared’s Standup Tour: Jared plugs upcoming tour dates, stressing the value of buying tickets early—a transactional way of “supporting” comedians (27:00).

3. Main Dating Discussion: First Email – The Accidental ‘Unmatch’?

• The Dilemma: A listener (“John”) is unmatched after a seemingly successful first Hinge date and wonders if it was a UI mistake or a purposeful rejection (32:40).
  • Jared and Jordana debate the merits of reaching out off-app:
    • Jordana: “There's no harm in finding her Instagram and DMing, as long as you give her an easy out—say if it was on purpose, she doesn’t have to reply.” (41:13)
    • Jared: “Let them off the hook… you get one shot, but don’t let yourself become a problem for them.” (48:11)
  • Cultural Reflection: The two riff on how our minds always search for exceptions (“maybe it was a mistake!”), but most of the time, unmatching is intentional, and we have to accept the 9/10 reality (44:33).

4. Icky or Picky: “Have a Good Day” Guy

• Scenario: A woman delays setting up a date due to a friend visiting, only to receive a string of increasingly angsty messages from her match, culminating in indignation and condescension over basic texting etiquette (54:00).
  • “What the **** am I supposed to do with ‘have a great day’?!” (55:45)
  • Hosts agree: this is textbook ick—red flag, and major bullet dodged.
  • Jared cautions: “People who say ‘let’s cut the bullshit’ and go to the date are usually the worst…you’re not cutting through anything. You’re just being an asshole.” (59:04)
  • Jordana: “This is someone who could be dangerous…It’s great when people can tell you who they are before you even meet.” (59:18)

5. The Roommate Romance Deep Dive

• Email: The episode’s titular dilemma—“I have a crush on my roommate, but he’s pining for someone else. Should I shoot my shot or risk our friendship/living situation?” (60:51)
  • The hosts explore the layers of this messy situation:
    • Jared: “He wants to be this guy for a woman who won’t commit to him. Just because you’re there doesn’t mean he wants to be that guy for you.” (63:49)
    • Jordana outlines possible scenarios:
      • He’s attracted but doesn’t want to risk the home harmony.
      • He’s not interested but enjoys the ego boost.
      • If he truly wanted to date her, he likely would have made a move.
    • Advice roadmap:
      • Step 1: “Get away from the apartment—see whether he makes time for you as a friend outside.” (69:25)
      • If yes: After a successful hangout, express your feelings with a no-pressure text and let him know you’ll need some space if he’s not interested.
      • If no: Accept and move on.
    • On physical intimacy: Jordana recommends withholding sex until the relationship is defined, referencing Hannah Brown’s “Fantasy Suite” approach in The Bachelorette.
      - “If you need the sex to make your decision, you’re not the person for me.” – Jared via Hannah Brown (76:09)
  • Honest, nuanced look at roommate dating, cautioning against prioritizing fantasy over reality and advocating for clear communication.

6. Rapid-Fire Listener Q&A – “Red Flag or Deal Breaker?”

• Venmo-ing for Sushi Before Dinner (81:04)
  • Both agree: Tacky to demand payment pre-sushi, but expecting him to pay for everyone may be unrealistic. “It rings unfuckable, but it’s a red flag, not a deal breaker.” – Jared (85:38)
• Using a Groupon on the First Date (87:24)
  • Both: Multiple behaviors combine to a deal breaker; one-off savings is acceptable, but compounding frugal signals (“whatever’s cheapest”, Groupon) shows a mismatched money philosophy.
• No Communication Guy + Prefrontal Cortex Excuses (91:46)
  • A listener is confused by a man who never texts but puts effort into in-person dates, then blames forgetfulness on “underdeveloped prefrontal cortex.”
    • “If he can’t remember anything about you after that many dates, it’s because he’s not really invested… If someone has bad communication, it’s usually not because of the prefrontal cortex.” – Jordana (98:06)

Notable Quotes & Memorable Moments

• “There’s lore here… I want to interview McFingers.” – Jared (07:09)
• On Winnipeg pride vs. stereotype:
  “You get there and they’re like, ‘We suck, we’re trash.’ … but honestly, it was great!” – Jared (16:00)
• “I think losing tackle football is a bad thing for society.” – Jared, after discussing his Fat Athletes of America Forever AIM name (35:30)
• “I think this is someone who would be verbally abusive… he has an anger problem. Go to anger management.” – Jordana (59:18)
• “He’s not going ‘What? Jessica wants me?’, it’s not how it’s promoted in the romcoms!” – Jared, on roommate romance (65:29)
• “Life is choosing which uncomfortable you want.” – Jared, discussing whether to confess feelings or suppress them (75:10)
• “Cheapness and boobs and ass… it’s all personal taste. Cheapness, you can’t see on somebody.” – Jared (87:53)
• “If you have to blame an underdeveloped prefrontal cortex for not responding, we’re in trouble.” – Jordana (98:06)

Timestamps for Major Segments (MM:SS)

• [04:45] – Jordana’s birthday stories & McFingers
• [16:00] – Winnipeg travel tales & souvenirs
• [32:38] – Listener email: The accidental dating app unmatch?
• [54:00] – Icky or picky: The “Have a great day” match goes off the rails
• [60:51] – Main topic: Should you date your roommate?
• [81:04] – Red flag or deal breaker: Venmo and sushi
• [87:24] – Red flag or deal breaker: Groupon on a date
• [91:46] – Red flag or deal breaker: Prefrontal cortex excuses

Tone and Language

True to the “U Up?” brand, the tone of the episode is honest, irreverent, and playful, mixing warmth with light roasting. The hosts riff on their own dating lives as much as those of the listeners, striking a balance between empathy for dating frustrations and a refusal to indulge in delusion. The dialogue is peppered with comedic banter (“TD Freed”, “McFingers”, “the titty shot glass saga”) but anchored by insights about communication styles, self-awareness, and the realities of modern romance.

Takeaways

• Be real about dating app mishaps. Unmatching is rarely accidental—and even if it was, a single polite, non-pressuring follow-up is the most you should ever do.
• Boundaries are necessary when crushing on a roommate. Test your dynamic outside the home; only advance if you’re ready for all outcomes (and consequences).
• Financial compatibility matters—just as much as chemistry. Frugality, generous gestures, and timing of money talk can reveal deep differences.
• Don’t romanticize red flags. Early warning signs (anger, control, blame-shifting) should not be overlooked.
• Lead with communication and self-respect. Whether dealing with dating uncertainty or a homefront crush, expressing yourself honestly (and giving the other person space to respond or not) is always best.

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