U Up? — “Is a Boudoir Shoot As Christmas Present a Good Gift?”

Hosts: Jordana Abraham & Jared Freid

Date: December 19, 2025

Episode Overview

In this festive episode, Jordana and Jared dive into the intricacies of holiday dating, the unique social energy of the season, and, most centrally, the question of whether a boudoir photo shoot makes for a good Christmas present. Using their trademark blend of honesty, humor, and lived experience, they tackle dating etiquette, gift-giving expectations, and the nuances of communicating in relationships—especially when it comes to sexual intimacy and personalization of gifts.

Main Themes and Purpose

• Navigating holiday dating and the romantic potential of the season
• Evaluating intimate or creative gifts, especially the boudoir photo shoot
• Communication around sex, intimacy, and expectations in new and established relationships
• The importance of self-confidence and self-motivation in dating and relationships

Key Discussion Points & Insights

1. Holiday Spirit and Social Dynamics

(00:53 - 04:44)

• The holidays are seen as prime time not just for romance, but also as an opportunity to make social connections and “PR” yourself—be upfront about being single and open to setups.
• Jared: “This time of year is the best time of year to be your best PR agent. ...You can't hide you're singled up.”
• Jordana: Advocates the power of manifesting, but in a grounded, practical way—being present and open with your intentions.

2. Personal Updates & Social Rituals

(05:02 - 11:16)

• Jordana shares she's hosting mahjong night, highlighting the social evolution from wild nights out to more mature, home-based gatherings.
• Jordana: “That's how I know I'm getting into, like, a weird age bracket.”
• Jared: Jokes about suburban life and contrasts it with his stand-up gigs, adding levity.

3. Jared’s New Book: “Walking Red Flag”

(15:26 - 24:02)

• Jared’s forthcoming dating advice book is officially in pre-order, prompting a discussion on the significance of pre-orders and the vulnerability required to write honestly about personal dating missteps.
• Book is a memoir/advice blend, following the arc from getting dumped, navigating apps, ‘first date to breakup’—with a focus on stories and mistakes:
  • Jared: “If you’ve ever wondered what’s going on through the mind of a man that you're dating, you are going to find a very vulnerable and true take.”
• Discussion on gift-giving, the discomfort of ‘support’ language, and the tension between selling art and asking for favors.

4. “Icky or Picky” Segment: Sex, Edging, and Communication

(26:50 - 32:39)

• Listener letter describes her boyfriend’s sexual practice of ‘edging’ (delaying ejaculation), which she only discovers mid-act, making her feel confused and put-upon.
  • Jared: “This isn’t all for you. You have to be cognizant that someone is doing something nice for you—like, they’re going down on you, they want you to feel good.”
  • Both agree there are time limits to certain acts and that mutual communication is key—no one wants to accidentally become part of someone’s kink without knowing it.
• Jared: “Don’t let me find out that I’m in on a kink I had no idea I was doing.” (32:28)

5. Boudoir Photo Shoots as Gifts: Good or Gimmick?

(32:41 - 41:16)

• Listener asks if giving her boyfriend an album of boudoir photos is a good holiday gift—she considered it both for him and to boost her own confidence.
  • Jared: “I would like this… but I’d have to be in a relationship.” (33:23)
  • He worries about his reaction not living up to her hopes; is unsure what men are supposed to do with such a gift (“Do I bring it with me on the road?”).
  • Both discuss that gifts like this often mean more to the giver than the receiver, especially since men tend to be “simple visual creatures.”
  • Jordana: “You have to know your audience…Manage your expectations around whatever his personality type is.”
  • Jared compares it to the uncertainty of how to behave at concerts—sometimes people just don’t know how to appropriately react, but it doesn’t mean they don’t appreciate the gesture.
• Discussion of whether a man doing a boudoir shoot for a woman would have the same effect (spoiler: it would not—Jordana finds authenticity more attractive than a man trying to look sexy).
  • Jordana: “Something about a man trying really hard to look hot makes it less hot.” (41:39)
• The advice: if you do a boudoir shoot, do it mainly for yourself and don't attach your self-worth to the recipient’s reaction.

6. Memorable Quotes & Banter

• Jared: “They don't make a lot of romcoms about dating in February, right?” (04:44)
• On the book:
  • Jared: “Every chapter of the book takes you from being dumped to then dumping someone again. So it takes you through all the life cycle, the life cycle of a relationship, which is all I know.”
• On blow jobs as labor:
  • Jared: “They don’t call it blow fun.” (29:44)
• On boudoir gifts:
  • Jared: “I think the sexiest part is that she did it. …The confidence, the sexuality—knowing a woman, like, I think for a lot of men, for me, hearing a woman talk about what she likes and what makes her feel turned on—you kind of rarely hear that.” (40:01)

Segment Timestamps

• [00:34] – Holiday party season & the best time for being open about being single
• [05:12] – Suburban mahjong, adult hobbies, and friendship rituals
• [15:26] – Pre-order panic and the process of writing “Walking Red Flag”
• [26:50] – “Icky or Picky” segment: Edging, sexual communication, and unintentional kinks
• [32:41] – Boudoir shoot debate: For you, for them, and for your confidence
• [41:00+] – What makes a man sexy (hint: not a boudoir shoot)
• [42:24] – Episode close, next week’s Christmas episode teaser

Key Takeaways

• Holiday season is prime time to be social and honest about your relationship status.
• Don’t be afraid to do or receive unconventional gifts, but manage your expectations—especially in how others react.
• Sexual communication—like any other aspect of relationships—is best done openly, not as a surprise maneuver.
• Boudoir shoots can be empowering and fun for the giver, but don’t hinge the recipient’s reaction to your self-worth.
• Self-knowledge and realistic expectations make for better gifts and better relationships.
• Above all: Humor, vulnerability, and communication are the heart of modern dating.

Notable Quotes with Timestamps

• “This time of year is the best time of year to be your best PR agent… You can't hide you're singled up.” — Jared (01:05)
• “Don't let me find out that I'm in on a kink that I had no idea I was doing.” — Jared (32:28)
• “Something about a man trying really hard to look hot makes it less hot.” — Jordana (41:39)
• “The sexiest part is that she did it right. Like, that to me, makes me drool… the confidence, the sexuality.” — Jared (40:01)
• “You have to know your audience…Manage your expectations around whatever his personality type is.” — Jordana (35:56)

This episode provides signature U Up? wisdom: sharp, self-aware, honest, and a little self-deprecating. Whether you’re considering a sultry photo shoot or just want to feel less weird about your suburban game night, Jordana and Jared help you laugh and learn about what makes relationships—and the holidays—so complicated, awkward, and special.