Girls Gotta Eat — “Why is Having a Boyfriend Embarrassing Now?” Podcast: Girls Gotta Eat (Dear Media)
Episode Date: November 24, 2025
Hosts: Ashley Hesseltine (A), Rayna Greenberg (B)

Overview

In this episode—recorded during Thanksgiving week—Ashley and Rayna dig into a viral British Vogue opinion piece titled "Is Having a Boyfriend Embarrassing Now?" by Shantae Joseph. They dissect the cultural shift around dating, public perceptions of relationships, and why so many women feel less inclined to flaunt their partners online. With their signature blend of humor and hard-hitting social commentary, the co-hosts reflect on how dating norms have evolved, the impact on women’s identities, and the new status of singlehood. They also field personal updates, discuss prenups, and, in true GGE fashion, close with a rundown of pop culture's most embarrassing fictional boyfriends.

Episode Structure & Key Themes

Thanksgiving Updates & Personal Catch-Up (00:33–08:00)

• The hosts share Thanksgiving plans and travel (Ashley to London/Paris, Rayna to Pittsburgh).
• Discussion of recent projects, including their most intensive episode (“the documentary”) and appreciation for their audience.
• Mention of “Vibes Only”—their sexual wellness brand—and upcoming sales (notable for the recurring tongue-in-cheek line: “We want you guys to go fuck yourselves.” [06:01]).
• Rayna details her foray into solo standup comedy: “I got my heart pretty shattered at the end of last year…I just started writing about it, and I really enjoyed it…I think I have some really solid comedy hour content.” [08:41]

The Prenup Journey & Marriage Realities (22:37–38:52)

• Ashley details why she and her husband chose to sign a prenup, the administrative and emotional realities of marriage, and the case for modernizing prenups.
• She endorses “Hello Prenup,” a tech-forward, cost-effective solution:
  “Their flat one time fee is $599 per couple…with the full package in the $2,000 range rather than $8,000+ via traditional attorneys.” [35:25]
• Points raised: community property laws, why some couples might reconsider marriage, the need for more open conflict style in relationships, and the importance of acknowledging debts and finances pre-marriage.
• Ashley re-centers the conversation: “Marriage in general is just not sexy. It’s paperwork, it’s government paperwork.” [38:54]

Spotlight Segment: “Is Having a Boyfriend Embarrassing Now?” (43:18–1:06:53)

Article Read & Initial Impressions

• Rayna and Ashley read/discuss Shantae Joseph’s British Vogue article, highlighting:
  • The shift from “boyfriend land” (women’s identities revolving around partners) to intentional decentering of men online.
  • The emergence of singlehood as a flex and the increased scrutiny (and even cringe) surrounding “boyfriend content” on social.
  • Quotes:
    • “If someone so much as says ‘my boy’ on social media, they’re muted.” [45:08, Author/Speaker: Shantae Joseph]
    • “Why does a boyfriend feel Republican?” [45:47, reader comment highlighted in article]
    • “Being partnered doesn’t affirm your womanhood anymore. It is no longer considered an achievement. It’s more of a flex to pronounce yourself single.” [46:15]
• The article’s viral impact, striking a nerve for questioning “the end goal” of womanhood and the status attached to being coupled.

Reflections and Cultural Analysis

• Hosts note a massive change in listener emails—now far more about single happiness and leaving unfulfilling relationships.
• Rayna: “Making your entire personality and identity about another person who might not even be worthy of it, that’s what’s embarrassing.” [50:19]
• Ashley on marriage now: “Women don’t need men anymore. Hot take.” [50:24]
• Discussion of “embarrassing” relationships, with Ashley emphasizing how women are waking up to not needing the traditional pathway:
  “If marriage benefited women, they would have taken it away from us by now.” [50:51]
• Both highlight single women’s newfound status, but stress the importance of not simply inverting societal shame: “What’s embarrassing is letting a man become your whole life and abandoning your friendships…” [53:45]

Social Media & Relationship Portrayal

• The hosts unpack Instagram “soft launches,” the decline of influencer couple content, and the evolving nature of public/private relationships.
• Ashley: “We just need to stop policing women—whether you choose to make a partner a big part of your world publicly or not, I support both.” [56:32]
• Both agree: consistent critique and “policing” of women’s choices is the real problem.

Notable Quotes & Moments

• Rayna on the new landscape: “I have never been more single than I am today…I feel more comfortable in my single time and happier than I ever have.” [55:03]
• Ashley recounts seeing TikToks of men speaking out against other men’s bad behavior: “Women are out here saying we're embarrassing. Men are behaving badly. We got to do better.” [62:26]
• Both stress: You should not stay in relationships that make your life worse just to avoid “being single.”

Recapping the Pop Culture Discourse: Most Embarrassing Fictional Boyfriends (70:37–78:55)

• In response to Vogue’s “13 Most Embarrassing Boyfriends in Pop Culture”:
  • Top “embarrassing” boyfriend: Mr. Big from Sex and the City.
    Rayna: “There’s nothing more embarrassing. And I love that we as a society…realizing what a toxic dumpster fire that was.” [71:25]
  • Runners up include Berger, Alexander Petrovsky, Trey McDougal, Warner from Legally Blonde, Ross Geller (Friends), Adam from Girls, and even Disney picks (Prince Eric, The Beast).
  • Ashley: “These worst boyfriends, to me, are not the outright assholes. They are the guys we were supposed to think were decent guys, and now the wool has been pulled back...” [75:00]

Timestamps for Key Segments

| Segment | Timestamp | |-----------------------------------------------|---------------| | Thanksgiving, Updates & Stand-up journey | 00:33–13:45 | | Ashley’s prenup experience | 22:37–38:52 | | Main Theme: Embarrassing Boyfriend Article | 43:18–1:06:53 | | Pop Culture Boyfriends Discourse | 70:37–78:55 |

Memorable Quotes

• On Standup & Audience:
  “Nothing makes me feel less scared than being in front of our audience.” — Rayna, [12:21]
• On Prenups:
  “You should be able to sign a thing that says, ‘I'm fucking leaving with what I came with.’” — Rayna, [31:54]
• On the Article’s Core Question:
  “Being partnered doesn’t affirm your womanhood anymore. It is no longer considered an achievement.” — Ashley, summarizing the article, [46:15]
• On Societal Shift:
  “Women don’t need men anymore. Hot take.” — Ashley, [50:24]
• On Avoiding Bad Relationships:
  “What’s embarrassing is being with someone who makes your life worse...just so you’re not single.” — Ashley, [53:45]
• On Social Pressure:
  “We just need to stop policing women. Whether you choose to make a partner a big part of your world publicly or you choose to decenter them, I support both.” — Ashley, [56:32]
• On the Wedding:
  “It was nice to see that at the wedding…there were single people there looking hot, living their best life.” — Ashley, [66:53]
• On Internet Critiques:
  “Let’s bring reading comprehension back. Yeah, let’s make reading great again.” — Rayna, [69:59]

Overall Tone

The episode is comedic, candid, and empowering, mixing cultural criticism with classic Girls Gotta Eat banter. Ashley and Rayna balance hyper-relatable humor (“We want you guys to go fuck yourselves…so go stuff yourselves” [06:01]) with genuine reflections on relationships, identity, and societal standards. They’re never afraid of self-deprecation, and their insights will resonate with listeners regardless of their relationship status.

For Listeners

This episode sharply encapsulates ongoing debates about gender, relationships, and online representation—delivered with the signature warmth and irreverence that has defined Girls Gotta Eat since 2018. Whether you’re coupled, single, or simply fascinated by shifting cultural norms, this one is essential listening (and laughing).