U Up? Podcast Episode Summary

Episode: What Are the Rules of an Open Relationship? ft Ashley Gavin
Date: March 20, 2026
Hosts: Jared Freid
Guest: Ashley Gavin

Episode Overview

This episode of U Up? features comedian and podcaster Ashley Gavin as a co-host, joining Jared Freid for a candid, hilarious, and insightful discussion about dating, relationships, and above all, the nuances of open relationships. Ashley shares her personal experience navigating an open relationship, the rules she's established with her partner, and how transparency and communication set the tone. The episode also responds to listener emails about bisexuality and relationship double standards, along with engaging rounds of crowd-favorite dating games like Red Flag or Dealbreaker and Icky or Picky.

Key Discussion Points & Insights

1. Ashley’s Stand-Up, Audience Dynamics, & Identity (01:13–06:00)

• Ashley discusses her stand-up career and the unique community at her live shows, where she regularly invites audience participation and builds an energetic, welcoming environment.
• Notably, Ashley attracts a diverse following, including bisexual women who sometimes experience new realizations about their sexuality at her shows.

Memorable Moment:
Ashley: "It feels like there's a moment in the show where you're like, all right, let me hear from you people ... They bring signs, they bring stories" (03:21).

2. Lesbian/ Straight Male Friendship Dynamics (05:25–07:45)

• Jared and Ashley reflect on the under-discussed friendship between straight men and lesbian women, challenging stereotypes and celebrating platonic relationships across orientations.
• Ashley notes the pride straight women take in gay male friends and wishes the same openness existed for straight men befriending lesbians.

3. Ashley on Open Relationships: Structure & Rationale (07:54–12:22)

• Ashley reveals she's in an open relationship with her girlfriend, who is bisexual. They allow each other to have sexual encounters with others but not romantic relationships.
• She emphasizes clear rules, mutual consent, and regular check-ins as crucial for maintaining trust and preventing complications.
• Ashley also discusses how openness simplifies things, reducing games and ambiguity.
• The couple is transparent about hookups and even has monthly check-ins about their open arrangement.

Notable Quote:
Ashley: "We both can hook up with other people, but we can't do, like, relationships with other people" (08:33).

4. Navigating Jealousy, Boundaries, and Family Planning (11:06–13:13)

• The conversation addresses whether the open relationship can or should continue if they have children, acknowledging the need to consider a child’s understanding and consent (even if indirect).
• Ashley notes that many parents and married people reach out privately to share their own non-monogamous arrangements.

Memorable Quote:
Ashley: "When you have a family, there’s now another person who is not consenting" (11:21).

5. Safety, Gender, and Hookup Culture (14:10–16:07)

• Ashley highlights the difference in safety and stigma for women navigating casual sex: straight women often face judgment and real dangers, while lesbian encounters are generally less risky.
• She recounts a story of asking a hookup to put her knife in the hotel safe, illustrating unique dating hazards.

Quote:
Jared: "You know, you're not inviting a grizzly bear over" (14:25)
Ashley: "It's a fair fight if there's gonna be a fight" (14:27)

6. The Rules and Realities—Transparency in Open Relationships (19:33–21:17)

• Jared asks if fights ever break out about their arrangement. Ashley says she and her girlfriend rarely argue, instead relying on monthly, honesty-driven conversations to address feelings and boundaries.
• They agree it's easier to maintain trust when the rules are clearly defined versus the ambiguity in monogamous relationships.

Notable Quote:
Ashley: "I think it’s easier to cheat when you just don’t have an established idea of what cheating means" (20:15).

7. Listener Email: Bisexuality, Shame, & Partner Insecurity (22:45–28:29)

• A listener asks if her boyfriend’s harsh response to her past same-sex kiss is a red flag or dealbreaker.
• Ashley and Jared dissect the implied shame and double standards, affirming that the listener is valid in her bisexual curiosity and criticizing the boyfriend's lack of empathy.
• The consensus: his behavior is a clear dealbreaker.

Quote:
Ashley: "Dear listener, you are bisexual. Okay, just stop trying to make caveats" (24:00).

Notable Quotes & Memorable Moments

• On Open Relationships & Simplicity:
  Ashley: "When everything’s out, it makes it so easy ... There’s no games." (10:15)

• On Transparency Over Rule-Breaking:
  Ashley: "I would be more upset if you lied about something rather than if you broke the rules and told me." (20:49)

• On Bi-curiosity & Shame:
  Ashley: "There’s so much shame in this, right? ... It is okay for you to be bi. Like, whatever." (24:15)

• On Navigating Adult Life & Roommates:
  Jared: "If you were to say anyone with a roommate is undateable after the age of 35, I would say that you are living by another time’s standards." (38:10)

Timestamps for Key Segments

• Ashley Introduced, Show Energy, Stand-up Comedy: 01:13–04:50
• Audience Stories, Bisexual Realizations, Community Feel: 04:51–06:00
• Straight Men & Lesbian Friendships: 05:25–07:45
• Open Relationships: How They Work, Rules, and Logistics: 07:54–12:22
• Jealousy, Kid Concerns, Secrecy: 11:06–13:13
• On-the-Road Hookups and Safety: 13:27–16:08
• Red Flag/Dealbreaker Game — No Arguments, Monthly Check-Ins: 19:33–21:17
• Listener Email: Bisexual Experience & Boyfriend Reactions: 22:45–28:29
• Best Cities for Meeting Women, Hookup Anecdotes: 29:12–31:09
• Icky or Picky Game — Roommates and Adult Lifestyles: 32:06–39:39

Dating Games & Listener Advice

Red Flag or Dealbreaker:

• Explored transparency, fairness, and emotional maturity in response to relationship dilemmas.

Icky or Picky (32:06–39:39):

• Discussed adult roommates from a non-judgmental, context-driven perspective.
• Stressed the importance of understanding generational differences, economic realities, and personal values over arbitrary age-based standards.

Overall Tone & Takeaways

• The episode is frank, playful, and supportive, peppered with Ashley’s sharp wit and both hosts’ honest insights.
• The conversation champions the necessity of communication, self-awareness, and non-judgment in modern relationships.
• Ashley’s candid sharing of her open relationship offers valuable lessons on boundaries, trust, and individual growth.
• The hosts encourage listeners to be less rigid about norms—whether it’s sexual orientation, relationship models, or lifestyle choices like living with a roommate at 35.

Final Note

Ashley Gavin:
"Just be on the same page as him and his life ... and make sure it's on the same page as your life." (39:54)

Jared Freid:
"We are living under the lens of our parents’ generation ... If you were to say anyone with a roommate is undateable after the age of 35, I would say that you are living by another time’s standards." (38:10)

Follow Ashley Gavin:

• Instagram, TikTok: @ashleygavin
• Podcasts: What's News With You? (with Josh Johnson); We're Having Gay Sex

Follow U Up?

• Instagram: @u.up.podcast
• YouTube: http://youtube.com/betches

For more detailed conversations and dating content, check out the full episode on your favorite podcast app.