Girls Gotta Eat: "Location Sharing and Big D*ck Problems" with Anna Roisman
Release Date: December 8, 2025
Hosts: Ashley Hesseltine (A), Rayna Greenberg (C)
Guest: Anna Roisman (B)
Episode Overview
This episode dives deep into modern relationship dynamics with Girls Gotta Eat’s signature humor—unpacking everything from uncomfortable wardrobe choices and location sharing to unforgettable stories about sex, dating, and awkward family encounters. Special guest Anna Roisman, comedian and impressionist, joins with hilarious insights, tales from her long-term relationship, and a Kris Jenner impression that steals the show. The team also tackles listener questions about hygiene dealbreakers, insecurity-induced icks, and—yes—what to do about a boyfriend with a penis that’s just too big.
Key Discussion Points & Insights
1. Bodysuit Trauma and Dressing Discomfort
[00:24–02:22]
- Rayna and Ashley share stories about bodysuits, thongs, and labia discomfort.
- Discussion on why women accept discomfort for fashion and evolving personal standards.
- Ashley references a White Lotus quote:
"I'm just not meant to live an uncomfortable life. And I think about it every time I put a thong in my labia." ([01:19], Ashley)
- Laughter about the humiliating logistics of undressing and bodysuit snaps.
2. Regional Slang & Lexicon
[04:01–06:03]
- Fun chat about regional terms like "kick off," meaning to start drama, and "bagging up" for laughing a lot.
- Ashley's Delaware and Philly ties highlighted; explains Delco = Delaware County.
3. Travel, Family Visits & the Humbling Experience of Staying with Parents
[07:45–11:52]
- Rayna recounts travels between London, Soho Farmhouse, and Pittsburgh, citing exhaustion and the awkwardness of being a guest as an adult.
- Ashley observes:
"Nothing humbles you and makes you feel like you shouldn’t be allowed to be a grownup in this world than, like, staying at your parents' house." ([08:15])
- Both discuss the merits of only staying in hotels nicer than your own home.
4. Hotel Room Stories: Nudes, Fart Walks, and Adult Sleepovers
[12:21–16:53]
- Rayna describes bonding with a friend by unapologetically taking nudes in their shared hotel room.
- Ashley hilariously describes her husband, Shashank, taking a "fart walk" down the hotel hallway to spare her, but the fart is still audibly epic.
"He was like, I was all the way at the elevators." ([15:13], Ashley)
- Amusing debate on privacy, comfort, and relationship milestones.
5. Family & Sibling Dynamics
[16:55–18:24]
- Ashley celebrates time with her nephews and describes distinct personalities, projecting on their future.
- Rayna reflects on family holiday traditions.
6. Plane Etiquette: Worst Behaviors
[18:24–20:54]
- Rayna’s horror story about a plane neighbor: man-spreading, turning on overhead lights, rolling pants up, taking shoes off—but shockingly, watching softcore (Netflix’s "Hunting Wives") in full view.
"He is just bricked up next to me on this flight, this man watching Hunting Wives." ([19:24], Rayna)
- Both ponder the etiquette around watching explicit content publicly.
7. Unexpected Encounters: Funeral Fiasco & "Big Dick Guy’s Mom"
[21:01–25:48]
- Rayna shares a mortifying funeral moment: a woman recognizes her and says, in front of her dad and aunt, “You hooked up with my son”—referring to a legendary hand job at summer camp.
"You hooked up with my son. She said it with her whole chest." ([23:31], Rayna)
- Reflections on adolescent sexual milestones and hilarious speculation about the "hand job to end all hand jobs."
8. Introducing Anna Roisman
[29:38–34:05]
- Anna recaps her career as comedian, host, HQ Trivia anchor, and viral impressionist.
- Famous for impressions of Kris Jenner, Steve (from SATC), Hilaria Baldwin (including a viral TikTok).
- Anecdote: Anna’s Hilaria impression caught Melissa Rivers' attention, resulting in a three-hour dinner:
"To have her blessing … that is the biggest compliment." ([32:51], Anna)
- Anna collaborated briefly with Hilaria Baldwin for a video—details on internet backlash.
9. Life as an Impressionist & Content Creator
[34:43–38:40]
- Anna grew up impersonating people, mastered her craft through UCB and pandemic lockdown content.
- (Steve impression originated in lockdown: "My boyfriend was like, this must be so funny if he’s laughing." [37:16])
- Dream job: Hosting late-night, sketch-heavy, Jimmy Kimmel-style show.
10. Anna’s Long-Term Relationship:
[38:47–41:24]
- Together with Jared for 9 years, met at UCB.
"I was in my sluttiest phase ever ... and left to hook up with a drummer." ([39:46], Anna)
- Met again at a small birthday dinner ("on amoxicillin and Jell-O shots")—Anna mooning on first date led to their WiFi password: RipSenorFrogs.
11. Dating, Marriage & Kids – To Wed or Not to Wed?
[52:03–56:39]
- When did people stop asking Anna about marriage? “After year six, they stopped.” ([52:30], Anna)
- Anna is candid: “I never cared about a dream wedding. I only cared about my career.” ([53:03])
- Wedding planning horror stories—her mother nearly ruined her sister’s wedding and soured Anna on the whole process.
- Kids? A clear “No,” decided on day one of their relationship.
12. Living with a Partner in NYC
[58:52–61:04]
- Anna and Jared’s one-bedroom apartment trials after living in LA with more space—confessed they need breathing room but are now “super codependent.”
-
"We live in the best area, great building, but yeah, we need our fucking space." ([59:07], Anna)
13. Location Sharing: Do or Don’t?
[61:07–65:14]
- Anna doesn’t share locations with Jared, but both can see “Andy,” a friend, and laugh about it.
- Hilarious reveal: Rayna admits to secretly tracking Ashley’s location for a month through a group chat mishap.
"This went on for a month ... every time I wanted to know where you were." ([62:55], Rayna)
14. Anna as Dating Guru & Matchmaker
[65:35–66:44]
- Friends approach Anna for blunt dating advice ("I'm not going to sugarcoat it. This person doesn't care about you.").
- Her track record: "Everyone I've set up has hooked up ... but they don’t date." ([66:07], Anna)
Listener Q&A / Relationship Problem Solving
[70:00–76:19] Listener Email 1: Hygiene Dealbreaker
- Listener’s partner has poor hygiene, showers rarely, and is grossing her out.
- Advice: Direct, compassionate honesty is crucial—frame improvements as leading to more intimacy.
"I would love to suck your dick more. Here’s how you can help yourself: please take a shower." ([71:08], Rayna)
- Anna’s wisdom:
"If this person’s not going to shower and gets in your bed every night, that’s disgusting." ([72:05], Anna)
[76:19–82:53] Listener Email 2: Insecure Boyfriend—"The Ick"
- Boyfriend, recently cheated on by a fiancée, is now suspicious over minor things (wallpaper, old Facebook pics).
- Hosts’ consensus: Validate feelings, have the conversation, but be cautious—early relational insecurity often signals bigger issues.
"If you have to write, 'Should I ride it out?' and it’s only been since May, that’s rough." ([78:54], Anna)
[84:36–93:14] Listener Email 3: “Too Well-Endowed” Boyfriend
- Listener feels ridiculous but says her boyfriend’s penis is so large sex is painful and daunting.
- Anna delivers a legendary Kris Jenner impression, sharing wisdom as if talking about Corey Gamble:
"You gotta look in the mirror and say to your vagina: You're doing amazing, sweetie." ([87:19], Anna/Kris)
- Real Talk: Use lots of lube, communicate, try gradual adaptation, but know when to accept physical limits. Painful sex can be a dealbreaker, and it’s not uncommon for things just to be, well, too big.
"You have to work a little harder for it, but if you want this person, try your best." ([91:45], Anna)
Notable Quotes & Memorable Moments
- "We are really excited for this. It’s our biggest show of the year. Wildest. Tons of entertainment. It’s gonna be so fun. It’s gonna be wild night Saturday night. Come get lit, get loose." ([07:04], Rayna)
- "There’s nothing that humbles you, makes you feel so like I shouldn't be allowed to be a grownup in this world than, like, staying at your parents' house." ([08:15], Ashley)
- "He was like, 'I was all the way at the elevators.' I was like, you went all the way down the hall? How did I hear that? We’re about to get a noise complaint." ([15:02], Ashley)
- On plane porn:
"He is just bricked up next to me on this flight, this man watching Hunting Wives." ([19:24], Rayna) - "You hooked up with my son. She said it with her old chest." ([23:31], Rayna)
Timestamps for Important Segments
- 00:24–02:22: Bodysuit & Fashion Discomfort
- 04:01–05:31: Slang Revelations
- 07:45–11:52: Family Visiting, Humility, and Hotel Life
- 12:21–16:53: Nude Photos & Fart Walks
- 18:24–20:54: Plane Behavior Horror Story
- 21:01–25:48: Funeral Hook-Up Reveal & “Big Dick Guy” Story
- 29:38–34:05: Anna Roisman Career & Impressions
- 38:47–41:24: Anna’s Relationship Beginnings
- 52:03–56:39: Marriage, Adulting, No Kids
- 61:07–65:14: Location Sharing Revelations
- 70:00–76:19: Hygiene Q&A
- 76:19–82:53: Insecure Boyfriend Q&A
- 84:36–93:14: Too Well-Endowed Q&A & Kris Jenner Impression
Tone & Atmosphere
- Comedic, raw, and open – The hosts and guest don't shy away from taboo or awkward details.
- Real-life modern dating dilemmas are presented both empathetically and hilariously.
- The vibe is "brunch with your most honest, funny friends."
Where to Find More
- Anna Roisman: @AnnaRoisman on Instagram; upcoming one-woman show "Triple Threat" at Joe’s Pub, January 7.
- Girls Gotta Eat: Official Website, Instagram, YouTube.
Share this episode with a friend—especially one who needs laugh-out-loud dating advice, a Kris Jenner impression, or reassurance that big dick and hygiene problems are, in fact, very real!