U Up? – "Decoding Weird Boyfriend Habits"
Hosts: Jordana Abraham & Jared Freid
Date: September 3, 2025
Overview
In this lively episode, Jordana Abraham and Jared Freid blend personal catch-ups with sharp, hilarious takes on modern dating dynamics. The main focus: ambiguous boyfriend habits, the "should I stay or should I go" dilemma, and decoding what’s really going on when relationships feel "good enough, but not great." Listeners write in with pressing dating questions, giving the hosts the chance to unpack indecision, attachment, and texting etiquette with their signature candor.
Main Segments & Key Discussions
1. Vacation Recap: Relationship Insights Abroad
[02:03–10:39] Jordana returns from her Euro trip
- Travel Chit-Chat: Jordana dishes on her couples/group getaway with her husband, reflecting on how travel impacts intimacy and conversation.
- “By the end of a trip, the last dinner, we’re like, so what have we not covered?” (Jordana, [04:04])
- Dynamics of Couples vs. Group Trips: Both hosts agree it’s nice to end with a couples trip after a group trip, for prime “debriefing” about friends.
- Authenticity Abroad: A hilarious moment when Jordana realizes the "authentic" restaurant Jared recommended in Lisbon was full of fellow New Yorkers.
- “Of course. You sent us to the basic bitch spot of Lisbon.” (Jordana, [06:35])
- Reflection: Jared ties the vibe of travel to personal growth within relationships, noting how changing environments alter perspectives.
2. Sex and the City Parallels, Modern Dating Media
[10:39–17:14] Jared’s Magazine Fears
- Jared Discusses His Interview: He shares anxieties about an upcoming article about him in The Cut, drawing a parallel to Carrie Bradshaw’s infamous “Single and Fabulous?” cover.
- “Honestly, I’ve been telling people about this article… I’m a little anxious about it. This is my single and fabulous question mark moment.” (Jared, [15:49])
- Broader Media Narratives: Discussion of how articles about “what’s wrong with men” or “single women” tend to spark debate and often feature strong viewpoints designed to go viral.
- Societal Blame: Both hosts dissect the blame-game in dating commentary: are single women “too picky” or are men “not stepping up”? And does the narrative ever really serve singles productively?
3. Cuff It or Cut It Off: "Good Enough" Dilemma
[24:33–43:06] Sponsored by Abercrombie – Listener Advice Column
The Listener's Dilemma:
A 27-year-old man writes in, unsure if he should take things to the next level with a woman who is “funny enough, smart enough, pretty enough,” but not spark-inducing.
- Honest Male Perspective: Jared empathizes deeply, noting he’s been in the same position. Both agree many people—regardless of gender—often wonder if there’s someone “better.”
- Choice Overload & Dating Apps: Jordana reflects on how dating apps foster “grass is greener” thinking and indecision.
- “Shouldn’t I be head-over-heels? Have dating apps and social media messed with my perspective?” (Listener email, [27:04])
- Romance vs. Realism: Discussion references Logan Ury’s “secretary problem” (how long do you interview before hiring?), tying it to dating—when do you stop searching and commit?
- The Male Angst: Jared explains the “selfish” motivation at play: “It’s not about babies or family clocks, it’s about, ‘will I regret missing out on someone better?’” ([40:34])
- Hosts’ Verdict:
- Jared: “Are you excited for the next date? If you’d be just as excited to meet anyone else, end it.” ([37:50])
- Jordana: “If you never had to see them again, would you feel relieved?” ([38:15])
- Consensus: Cut it off if the excitement isn’t there. Better to be honest than string along a partner.
4. Petty or Prudent: Getting Stood Up Online
[46:18–54:36] Dating App Etiquette
- Scenario: A listener waits at a café for a date, only to realize the guy unmatched her on the app right before the meeting.
- Hosts’ Reaction:
- Jordana finds the unmatching strange and acknowledges the safety aspect.
- Jared: “When I unmatch, I want someone out of my life… It’s kind of a f*** off.” ([48:54])
- Takeaway: The listener’s decision not to go in is prudent, not petty. “Trust your instincts. That’s not petty—that’s protective.” (Jordana, [52:59])
5. Rapid-Fire Relationship Dilemmas (“Red Flag or Deal Breaker”)
[72:11–93:39] Hilarious Hot Takes
Weird Night Habits
- Scenario: A boyfriend secretly watches gaming live streams to fall asleep.
- Jordana: Not a deal breaker; in fact, “almost a green flag” that he’s slightly embarrassed—he cares what you think.
- Jared: “Anyone with a ‘sleep strategy’ is a little embarrassed… whatever works!” ([75:17])
“The Five-Year Engagement”
- Listener: Boyfriend keeps stalling on proposing after four years, citing residency, stress, and lack of money.
- Hosts: He’s avoiding the real conversation. Jordana: “When you have four excuses, you have none.” ([86:28])
- Real advice: Demand clarity. Don’t negotiate against yourself.
“The Bad Texter”
- Listener: After six dates, boyfriend takes days to reply, despite having already discussed it.
- Jared: “I feel let down… If you’re dating someone, you want to feel prioritized.” ([91:56])
- Jordana: “Stop saying it makes you feel weird. Replace ‘weird’ with ‘de-prioritized’ or ‘turned off.’” ([91:08])
- Verdict: Raise the real issue or walk away if your needs aren’t being met.
6. Interlude: Audience Email—Should She Stay or Go?
[57:14–67:31] The "Timing" Problem
- Listener Note: Met a great guy right after moving out from her last relationship; things escalated quickly but she panics, longing for more single time.
- Jared & Jordana: This mirrors the “good enough” dilemma from earlier: timing is its own problem. If you’re already questioning, you’re usually not ready.
- Jordana: “Passing a note that says ‘please help’ while you’re at a show with your date? That’s telling. You don’t want to lose someone if you’re doing that.” ([69:22])
- Consensus: Be honest and let him go if your heart’s not in it.
Noteworthy Quotes & Moments
- “This could be me from the past writing [this email].” – Jared, on the "good enough" question ([28:34])
- “Trust your instincts. That’s not petty—that’s protective.” – Jordana, on skipping a date after being unmatched ([52:59])
- “When you have four excuses, you have none.” – Jordana, on proposal delays ([86:28])
- “If someone wants to make you a weirdo, it’s very easy to do that!” – Jared, on embarrassing personal habits ([76:21])
Episode Timestamps (Highlights)
- 02:03 - Jordana’s Euro trip recap & couples’ vacation dynamics
- 10:39 - The Cut article, Sex and the City parallels
- 24:33 - "Cuff It or Cut It Off" advice segment: When is ‘good enough,’ enough?
- 46:18 - Petty or Prudent: The case of the vanishing date
- 54:39 - Passing notes at a comedy show: ‘Is timing the problem—or is it him?’
- 72:11 - Red Flag or Deal Breaker rapid-fire
- 91:56 - “The Bad Texter and the Meaning of Priority in Dating”
Tone & Style
Conversational, hilarious, and unfiltered, Jordana and Jared blend deeply sympathetic advice with on-point social commentary and frequent self-deprecating humor. The show feels like both a late-night therapy session and a group chat—refreshing, affirming, and a little bit “did they just say that?”
Best for:
Listeners struggling with ambiguous dating situations, confused by 'the spark,' sick of bad texters, or just wanting to laugh at the absurdity of millennial dating.
Listen for:
Sharp takes on emotional risk, vulnerability, decision-making, and why sometimes, cutting it off for honest reasons is the most loving thing—for everyone.
For more on listener questions, bonus episodes, and hilarious dating commentary, follow @u.up.podcast on Instagram or subscribe for early releases and exclusives.