Can I Spend Valentine’s Day With My Situationship? (Lightning Round Special) - U Up?

Transcript

A (0:00)

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B (1:04)

Batches the most honest hookup night of the year. How about that?

A (1:09)

I love it.

B (1:10)

What a rebrand of Valentine's Day.

A (1:14)

Hello and welcome back to the UF podcast special Valentine's Day episode. I'm Jordana Abraham.

B (1:20)

And I am Jared Cupid Fried. Here to make all your love dreams come true. Ho ho ho. Merry Valentine's Day. Is that what. I don't even know if Cupid has a voice.

A (1:35)

Cupid's a baby. You should get a diaper.

B (1:37)

I would have worn a diaper. I wore my. My onesie. Here. I'm back in shorts.

A (1:42)

Back in shorts.

B (1:43)

For any of the women that enjoyed my my camel toe from dinner and a show. Yeah, from the earlier episode. How are you? What's going on Friday feels Happy Valentine's Day to you.

A (1:54)

Valentine's Day. We are back with another Valentine's Day.

B (1:58)

Listen, if you're listening to us, it may be someone was like, this will get you in a better mood. You know, I, I think this is like, if you're a listener of the podcast, what a perfect thing to send to your friend who's like upset on Valentine's Day. Maybe like is thinking about it. Maybe they're alone. Maybe they're wondering what's going on with their partner. This is A great episode to send them.

Summary

U Up? Podcast Summary

Episode: Can I Spend Valentine’s Day With My Situationship? (Lightning Round Special)
Hosts: Jordana Abraham & Jared Freid
Date: February 14, 2025

Overview

This special Valentine’s Day episode of U Up? is lively, funny, and filled with candid reflections on the none-too-simple emotions and rules of Valentine’s Day in modern dating. Hosts Jordana and Jared, in true form, laugh through the ups and downs of relationships, situationships, office flirtations, and everything in between. The centerpiece is a “lightning round” of listener questions (“Bogo or No Go”)—real-life conundrums around dating, love, and what you “should” do on the most loaded romantic holiday of the year.

Main Themes

Navigating Valentine’s Day—single, dating, or in a ‘situationship’
Who “owns” the holiday—Is it a couple’s, women’s, or everyone’s day?
Honest advice on boundaries, expectations, and self-worth in relationships
Empowerment to lean into your desires rather than dreading Valentine’s Day
Real listener dilemmas and success stories

Key Discussion Points & Insights

1. Rebranding Valentine’s Day (01:04–04:00)

The hosts joke about Valentine's as "the most honest hookup night of the year," with Jared donned as Cupid.
Jared: “What a rebrand of Valentine’s Day.” (02:14)
Both express that while it may feel like a women’s/couple’s holiday, it’s tough for singles—often serving as an uncomfortable, reflective day.

2. Is Valentine's Day a Gendered or Couple's Holiday? (02:39–06:25)

Traditionally seen as a women's holiday, but Jordana and Jared push back. They say it’s a couple's/romantic-love holiday, not for singles.
Jared on parents sending daughters flowers: “It sounds like sending flowers to a family who lost a loved one... It’s a Shiva call type of move.” (03:07)
Single people (esp. men) don't typically feel “left out” unless their social circle makes them feel bad.

3. Emotions and Expectations for Long-term vs. New Couples (06:25–08:15)

“If you are a real long-term, long-standing couple, you don’t give a shit about Valentine’s Day.” – Jordana (06:25)
New couples are more into the “fanfare”, with story of early excitement—flowers at work, cheesy gestures.

4. Cooking for Valentine’s (07:11–12:32)

Jordana and her boyfriend Mike are staying in this year for the first time—Mike cooking as a romantic gesture.
Culinary family anecdotes (Jared’s grandfather the butcher, family dinners).
“I think the acknowledgment, even if you’re in an older couple, just the like... even just saying Happy Valentine’s Day—isn’t that cute?” – Jared (06:36)

5. Lightning Round: “Bogo or No Go” Sponsored by Shake Shack (17:18–43:30)

Situationship Dilemma (18:57–27:39)

Listener in a new situationship, older woman/younger man; he seems hurt when she wants to keep it casual.
“Once someone has said they want more, is it enjoyable to the person on the other end to keep hanging out?... There’s a tension.” – Jordana (21:30)
“You’re getting what you want and they’re losing out on what they want. And that is seen as the more, you know, noble quest.” – Jared (22:23)
Advice: If you know you’re not on the same page and the other person wants more, it’s mature to end things to prevent further hurt.

The Point of Situationships (23:23–24:53)

Situationships are never intentional; one person always wants more. “No one goes looking for a situationship.” – Jordana
They typically waste time and emotionally block you from finding the right match.

Age gap (24:55–27:05)

Hosts’ take: If everyone’s consenting and legal, age gap is not an issue—unless it is for you. “You're so caught up in what other people think that you can't even enjoy your own life... When you find the right person, none of that will matter.” – Jared (25:39)
Both stress honesty about what you truly want.

Office Flirting (27:41–31:38)

Listener wonders if her office rapport with a coworker could lead to dating.
Advice: “Office relationships have to go very slowly. You have to bridge the office connection to the real world… Ask him to get drinks off-site and see if the vibe remains.” – Jared (29:49)

Relationship Commitment Anxiety (31:52–35:16)

Listener whose situationship turned official now worries “when is the other shoe going to drop?”
“I think she is totally right to be on edge here.” – Jordana (32:41)
Both advise: Go with it, but be honest about trust issues and communicate openly; “Lean into the relationship but say what you feel.”

Listener Success Story (39:42–45:10)

Touching letter from a listener who left a situationship after hearing the show’s advice, found her self-worth, and got engaged to a loving new partner.
“We are our own best things, and working on ourselves makes us the best partner to someone else.” (Email, 43:15)
Jared: “When you find the right person, none of that [social rules] will matter.”

6. The Lightning Questions (46:26–70:44)

When to Acknowledge Valentine's Day (46:26–53:34)

Acknowledging Valentine’s Day means a relationship is moving forward.
“If you’re talking to someone, acknowledgment of the day means that you are in a stronger relationship than you were before Valentine’s Day.” – Jared (46:51)
Non-acknowledgment or a text with no plan post-multiple dates = red flag.

Remote Valentine's Ideas (54:37–55:26)

Sex toy with app, cooking same recipe, starting a movie at the same time—“No one has better ideas for a relationship than a single guy who’s never had to do any of it.” – Jared (55:34)

“Valentine’s Day is Everyday” Excuse (55:59–58:24)

“This is the highest form of bullshittery.” – Jared (56:18)
Be direct: “Part of a relationship is doing things for other people because it makes them happy.” – Jordana (58:07)

How to Ask to Spend Valentine’s Together (59:16–61:54)

Go on offense: If you want something, ask for it directly. “If you don’t get what you want, there’s your argument.” – Jared (51:52)
“If you’re waking up the morning of Valentine’s Day, it’s already over.” – Jared (62:18)

Is Valentine’s Just for Women? Should Men Expect Gifts? (62:32–64:08)

“It’s a couple’s holiday... Men don’t expect gifts, but thoughtful gestures are nice.”

Lingerie—Yes or Gimmick? (64:23–66:09)

Lingerie is always appreciated for the effort, especially in a longer-term relationship.

Not Into Valentine’s—How to Tell Your Partner? (66:04–67:20)

Be honest about why, with vulnerability; it brings couples closer.

Giftless Boyfriend—Is it a Bad Sign? (67:21–68:08)

Depends on expectations and context—if he knew you expected a gift and didn’t deliver, it’s not great.

Spending Valentine’s on Date #2 or Alone (68:22–70:15)

It can be fun; just don’t overinterpret the meaning.
“It’s the most honest hookup night of the year… If you’re out, everyone else at the bar is single.” (69:38–70:08)

Host Story: Jordana’s parents met at a Valentine’s party with different dates, but ended up together. (70:15–70:44)

Notable Quotes & Memorable Moments

“No one goes looking for a situationship.” – Jordana (23:40)
“You’re getting what you want and they’re losing out on what they want. And that is seen as the more noble quest.” – Jared (22:23)
“Make Valentine’s Day your friend, not your foe... It’s time to say ‘I want what I want’.” – Jared (51:07)
“Feelings are valid. You want what you want; your needs are your needs.” – Jordana (52:03)
“This is the most honest dating day. There is no day that you’re going to get an answer like Valentine’s Day.” – Jared (49:10)
“All you’re doing is saying, I’m on this page. Today is a day where pages are announced.” – Jared (64:08)

Segment Timestamps

01:04 – Rebranding Valentine’s Day, holiday framing
02:39 – Is Valentine’s for women or couples?
06:25 – Long-term couples vs. new couples and the Valentine’s effect
17:18 – Bogo or No Go: Lightning Round begins
18:57 – Should I call off a situationship if he wants more?
27:41 – Office crushes: how to move from chit chat to dating
31:52 – Relationship anxiety post-situationship
39:42 – Listener writes in with engagement story (success story)
46:26 – Lightning round of Valentine's FAQ
51:07 – Empowerment: making Valentine’s Day “your friend, not your foe”
64:23 – Is lingerie still “worth it” on Valentine’s?
70:15 – Going out alone or third date on Valentine’s

Episode Tone & Language

Authentic, irreverent, comedic, and full of both empathy and straight-talk. The hosts are quick with a joke but also insist on emotional honesty and self-reflection, always reminding listeners to do what actually feels right for them, not what’s “expected.”

Summary Takeaways

Valentine’s Day exposes the realities and expectations in any romantic situation—use it to your benefit by asking for what you want and viewing it as a relationship stress-test.
Situationships rarely work for both parties; self-awareness and kindness require knowing when to end them.
There’s no universal timeline or standard for Valentine’s Day—communication and clarity are key.
Self-worth and honesty are non-negotiable, and it’s okay to lean into your desires, even (especially!) on Valentine’s Day.

Best for:
Whether single, dating, or “it’s complicated,” this episode offers laugh-out-loud moments, relatable confessions, and truly practical advice for surviving—and thriving—on Valentine’s Day.