U Up? Podcast Summary

Episode: Should I Break Up Before or After the Holidays?
Hosts: Jordana Abraham & Jared Freid
Date: November 28, 2025

Episode Overview

In this Friday Feels edition, Jordana and Jared dive deep into the perennial question: Should you break up before or after the holidays? They address listener dilemmas about sentimental partners, navigating family expectations, and the pros and cons of holiday breakups, all while weaving in their signature mix of humor, personal anecdotes, and relatable dating advice.

Key Discussion Points & Insights

1. Catching Up: Post-Thanksgiving & Black Friday Chatter

Timestamps: 02:28 – 13:00

• Thanksgiving Reflections:

  • Jared and Jordana discuss the aftermath of Thanksgiving and the shift into holiday shopping.
  • Black Friday habits: Jordana is a fan of online Black Friday deals (“Who is going to stores still?"), while Jared admits to impulse buys through Instagram ads—highlighting millennial shopping tendencies.

• Gift-Giving and Watch Talk:

  • Jared shares how watches are "male jewelry," a marker of personal style and sometimes status. Jordana relates this to women’s attachment to engagement rings.
  • On luxury shopping culture: “Can I just give you the money… and you just give me a watch?” – Jordana (06:20)

• Favorite Things Gift Exchange:

  • Jordana explains her “favorite thing” white elephant style party, where guests gift an under-$100 personal favorite item.
  • Skincare is a recurring theme: “I do start to understand the idea of like someone liking their face routine.” – Jared (13:57)

2. Listener Game: "Icky or Picky?"

Timestamps: 20:36 – 29:28

• Listener Dilemma: Sentimental Decor

  • A listener is “icked” by a boyfriend who displays his childhood macaroni art and glitter drawings in his living room after a Thanksgiving visit home.
  • Both hosts empathize with parents offloading childhood memorabilia (“There is an age where your parents think you’re just a storage closet.” – Jared, 21:52).
  • The key issue: Sentimentality vs. Taste. Jordana says displaying a couple of meaningful childhood items is fine, but “framed macaroni art in the living room? That’s weird.” – Jordana (25:20)
  • Jared references a Full House episode as a metaphor for meaningful keepsakes and discusses the line between cute nostalgia and emotional immaturity.

• Consensus:

  • They agree it’s a little picky to break up over this, but playful teasing is fair game:
    “I wouldn’t stop seeing someone because of it, but I would, like, be making fun of it.” – Jordana (28:52)

3. Main Topic: Breaking Up Before or After the Holidays

Timestamps: 30:42 – 36:51

• Listener Email: Six-Year Relationship Ordeal

  • A listener asks if she should break up with her boyfriend of six years before or after the holidays, given their relationship has “no sex” and they’re like “roommates”.

• Hosts’ Advice:

  • Act Quickly, Not Kindly:

    • “The kindest thing you can do for someone in that situation is to break up as soon as you know.” – Jordana (33:15)
    • Delaying a breakup for the holidays may seem polite, but it’s actually less humane. The partner deserves clarity and the ability to spend the holidays with support, rather than facing “the desert of loneliness” in January.
    • Jared’s memorable analogy:
      “Ending it on January 2nd is shoving them out to this cold nothing… Think of Siberia… just swirling wind and snowy ground and nothing.” (34:16)
    • The email itself shows the writer is already emotionally done—they encourage her to treat her happiness as a priority.

  • On Holiday Family Dynamics:

    • It’s preferable to break up before major gatherings than fake it through tense events.
      “There's nothing worse than spending a weekend with a couple that's about to break up.” – Jordana (36:02)

  • Healing Over the Holidays:

    • The holidays offer comfort and a support system, while January is statistically lonely.
      “They can go home, lick their wounds, and come back for the New Year, ready to use the dating apps.” – Jordana (36:48)

4. Notable Quotes & Memorable Moments

• On status symbols:

  • “It is male jewelry… [a watch] is my class, my success.” – Jared (07:04)

• On post-breakup timing:

  • “If you break up with someone January 2nd, that is just looking at the desert of loneliness.” – Jared (34:03)

• On post-breakup family support:

  • “They can go home to their family and be nestled in the bosom of love… food, love, blankets, old sweatpants.” – Jared (33:39)

• On relationship transitions:

  • “To go into a relationship, it has to go from me to we. To get out of a relationship, it has to go from we to me.” – Jared (32:04)

Timestamps for Important Segments

| Segment | Timestamp | |-------------------------------------------------------|------------| | Black Friday habits and gift traditions | 02:28–13:00| | “Icky or Picky” on sentimental childhood decor | 20:36–29:28| | Main topic: Break up before or after the holidays? | 30:42–36:51| | Notable quotes and reflections on family/holidays | Scattered; see above|

Overall Tone & Takeaways

• Conversational, self-deprecating humor: Both hosts balance personal vulnerability with relatable wit.
• Empathy and tough love: Sidestepping sugarcoating, they urge listeners to prioritize their happiness while respecting their partner’s dignity.
• Relatable modern dating insights: From male watches to “favorite things” parties, the episode seamlessly weaves cultural nuance into advice.

Bottom line:
If you’re questioning your relationship, especially leading into the holidays, don’t delay the inevitable. “The kindest thing you can do for someone is to set them free as soon as you know it’s over—no matter what the calendar says.”