The JTrain Podcast – "Horror or Horrific with Rory Uphold – Chit Chat Wednesday"

Host: Jared Freid
Guest: Rory Uphold (host of "Crime of the Heart" podcast, author of A Final Girl’s Guide to the Horrors of Dating)
Release Date: October 1, 2025

Episode Overview

This Chit Chat Wednesday features comedian and author Rory Uphold, diving into the “horrors of dating” through honest, funny, and thoughtful conversation. Together, Jared and Rory discuss Rory’s new book A Final Girl’s Guide to the Horrors of Dating, tales of romantic misadventure, and the importance of self-reflection and self-worth in modern dating. They recount personal stories, explore the impact of gendered socialization on relationship dynamics, and play a game judging dating scenarios as “horror” or “heroic.”

Key Discussion Points & Insights

1. The Inspiration Behind Rory’s Book

• Rory explains the inspiration for her book came from noticing how people are often told to “just get over” dating nightmares, no matter how emotionally impactful they are.
• “You could date someone for five years. They could cheat on you and break your heart and waste your time, and there's really nothing you can do about it. But if I key their car, that's a misdemeanor, right? … One seems worse to me.” (Rory, 01:56)
• The book isn’t just about blaming others: “Where do I take accountability? Like, how did I perpetuate this?... Part of the reason why it hurts so bad is that you kept getting back together with the person that treated you shitty, right?” (Rory, 04:20)

2. The “Final Girl” Trope and Its Dating Parallel

• The "final girl" is a horror movie trope—she's the last woman standing who survives to tell the tale (Rory, 05:25).
• Rory draws a parallel: “I’ve lived through and survived all of the dating horrors and lived to tell the tale… and I feel like I’ve collected enough advice to be like, you know, you don’t have to do it the way that I did it.” (Rory, 05:27)
• Confidence and self-worth play a central role in who we select as partners.

3. Writing Through Embarrassment and Growth

• Both discuss the vulnerability of writing about personal stories—especially re-living dark or embarrassing moments.
• “Some of them get…pretty dark. Like I did get into an abusive relationship…very embarrassing. Not something that like I would normally want to share …And yet it happened to me and I had to take a really close look at like, how did that happen and why did that happen and what did that look like?” (Rory, 06:54)
• Sex and sexual agency: Rory admits ignoring her own comfort and safety to be palatable or not a “buzzkill” in sex (09:11).
• “You’re gonna help someone who feels that way about themselves.” (Jared, 08:04)
• Jared on his own writing embarrassment: “I’m still talking about this, what? I’m a fucking loser, you know?…that’s how I felt like, you know, writing this.” (Jared, 11:54)
• The process of looking back at past relationships also means considering all the paths not taken.

4. The Gendered Experience of Dating Horrors

• “Women have way more horrific stories than men do in the dating world.” (Jared, 16:46)
• Rory’s hot take: “I think women were groomed to be chosen instead of being taught how to choose...so a lot of our issues stem from the fact that we're constantly trying to be chosen.” (Rory, 16:46)
• The pain of rejection gets internalized more deeply for women, often as a reflection of their own worth.

5. Modern Dating: In Real Life vs. Apps

• Rory describes her current relationship, sparked by a chance meeting at a real-life party (“I got the last like, chopper at a Nam. Yeah. It feels like.”—Rory, 18:27).
• Jared and Rory praise the power of in-person friend circles and meeting people organically.
• Advice: Don’t just pursue events for singles—genuinely build relationships and shared interests, as those networks lead to better romantic connections (Rory, 26:37).
• Quote Highlight: “Have a party where everyone—the cost of entry is one friend. They don't have to be single...bring one friend…now everyone at that party who's cool at an abandoned bowling alley in LA…” (Jared, 24:01)

6. The Value of Married Friends in Single Life

• Both emphasize the importance of hanging out with married friends, not just single ones, to expand your social (and potential dating) circle (Jared, 29:04).
• “Your friend’s husband is gonna make it happen for you.” (Jared, 29:04)

Notable Quotes & Memorable Moments

• “Women were groomed to be chosen instead of being taught how to choose.” – Rory Uphold (16:46)
• “You’re bringing those things up because you can now.” – Jared Freid (25:03)
• On dating apps: “It’s so hard to get off the app, and it's so hard to get someone to, like, you know, leave the casino, which is what they are...” – Jared Freid (26:11)
• On self-accountability: “You also betrayed yourself. Part of the reason why it hurts so bad is that you kept getting back together with the person that treated you shitty.” – Rory Uphold (04:20)
• On honest dating mishaps: “To turn and, like, make solid adult eye contact with me and be like, I have diarrhea. I have to go. Handle that. Handle that.” – Rory Uphold (35:37)
• “Papi got excited would send me to institution. I'm like, so we named our dick. Okay.” – Rory Uphold (40:18)

Game: Horror or Heroic?

(First prompt at 29:56)

Jared presents awkward dating scenarios; Rory judges them as “horror” or “heroic”:

• Introducing a past date as an ex at dinner:
  Heroic, not shameful. Openness and vulnerability win points.
  “There were choices to make, and he made the most difficult choice…” – Jared (31:37)

• Being honest about diarrhea mid-date:
  Heroic.
  “That’s wild. Because who the f*** would use that as a lie?...But then to…make solid adult eye contact with me and be like, I have diarrhea. I have to go.” – Rory (35:19)

• Forgetting wallet, asking for the check to be covered:
  Horror.
  “Who doesn’t bring a wallet to a date? That’s crazy town, right?” – Rory (36:13)

• Premature climax, then an awkward cuddle:
  Horror in delivery, not in the act itself.
  “Papi got excited would send me to institution. I’m like, so we named our dick. Okay.” – Rory (40:18)
  “The horror part isn’t that it happened. It’s how it’s being taken care [of].” – Jared (43:08)

Important Timestamps

| Time | Segment/Topic | |-----------|----------------------------------------------------| | 01:56 | Rory on the unfairness of dating heartbreak | | 04:20 | Self-accountability in dating struggles | | 05:25 | The “Final Girl” trope explained | | 06:54 | Rory shares about past abusive relationship | | 08:36 | Sex, sexual agency, and embarrassment | | 16:46 | Women’s unique challenges in dating | | 18:27-22:33| Rory’s “meet cute” real-life dating story | | 24:01 | Jared’s tip: “Bring one friend” to parties | | 26:11 | Dating app psychology & meeting “IRL” | | 29:56 | “Horror or Heroic?” game begins | | 35:16 | Diarrhea dating scenario | | 36:13 | Wallet-tap dating scenario | | 38:47 | “Papi got too excited” scenario | | 44:23 | Book promo code & wrap-up |

Additional Resources

• Book: A Final Girl’s Guide to the Horrors of Dating (use code JTRAIN15 for 15% off)
• Rory Uphold on Instagram: @couldbeblonder
• Podcast: Crime of the Heart

Episode Takeaways

• A Final Girl’s Guide to the Horrors of Dating is part-memoir, part-advice—Rory uses both personal and broader cultural insights to demystify and destigmatize the emotional pain of dating.
• The most potent dating lessons come from honest self-examination.
• Friendship circles and in-person connections remain powerful pathways to meaningful relationships.
• Humor and empathy—found in both Rory and Jared’s candor—lighten the weight of even the most horrific dating stories.

Use code JTRAIN15 at thehorrorsofdating.com for 15% off Rory's book.