The JTrain Podcast
Host: Jared Freid
Episode: My Date Canceled Because She Knows My Ex! Help! – MONDAY MAILBAG
Date: August 18, 2025

Episode Overview

In this engaging Mailbag Monday episode, Jared Freid tackles two listener emails about the complexities of modern dating—focusing on awkward overlap with exes and the pitfalls of casual, low-effort connections. With his candid humor and practical advice, Jared unpacks the nuances of relationships, breakups, and how to assert your needs while dating in a big city.

Key Discussion Points & Insights

1. Why Ask Jared? Why Mailbag Monday?

• Safest Space for Advice: Jared assures listeners it's a judgment-free zone:

  “This is kind of the safest place you can go with this. … I don’t know your backstory … to judge you on the information you’re tell.” (01:23)

• Value of Honest Feedback: Friends/family can soften the truth, while Jared brings unfiltered analysis.
• Jared leans heavily into the value of raw, immediate responses:

  “I like to be raw. … I hate when people say that … but you wouldn’t get this.” (08:20)

2. Email #1: Hinge Date Canceled—Recent Friend of an Ex (12:40–43:45)

Email Summary:

• Listener matches with a girl on Hinge, plans a date.
• She cancels after realizing he previously dated her (recent) friend, sending:
  “I think we should probably cancel. I just realized you’re actually a recent ex of a friend of mine. You seem great, though, and I wish you all the best.”
• The listener’s main concern: Was this her friend (his ex) interfering? Why not just go on the date?

Jared’s Analysis:

• Breakups Aren’t Amicable:

  “There is no such thing as an amicable breakup. … Every amicable breakup was started by one person who wanted to break up more.” (21:32)

• How Apps and Social Circles Intersect:

  • In a big city, accidental overlap with an ex’s friends is common and often innocent.
  • Women sometimes don’t publicize early relationships to friends to avoid embarrassment if things end.
  • It’s easier to opt out of a “complicated” date, especially when options are plentiful (“Hinge and Uber are the same thing.” 32:28).

• Dissecting the Cancel Message:

  • “We should probably cancel” is intentionally soft, leaving an opening for another attempt, but also avoiding direct rejection.
  • Jared emphasizes it’s not about the ex trash-talking the listener.

  • “I don’t think you should concern yourself with what the ex is saying. It’s not your problem. … You’ve been respectful.” (34:10)

• What Should the Listener Do?

  • If he truly feels a strong connection, it’s okay to send one more polite, earnest text (not pushy, not desperate).

    “If you think that this conversation really jumped off the screen … I do think you can … text the person again, like, ‘Hey, I just wanted to give this one more shot.’” (40:18)

  • Own the extra pressure—if you go out, it’s a “more pressurized date,” and you need to approach it thoughtfully.
  • Absolutely do not contact the ex to “clear things up”—that route only makes things messier.

Notable Quotes:

• “People opt for comfort over difficulty, and that’s okay. She should.” (32:56)
• “Let’s not get in the business of just saying ‘amicable’ when that doesn’t exist.” (22:10)
• “I don’t think your ex … is trashing you about town. … All you know is that this text ‘we should probably cancel’ is not ‘I have to cancel.’” (36:45)

3. Email #2: Volleyball Team Situationship (46:15–59:25)

Email Summary:

• Listener (early 30s, female) meets a guy via a friend’s volleyball team.
• He only asks her to hang out after Thursday games; texting is sparse, and the routine hasn’t progressed in a month.
• She’s communicated her desire to see him “beyond just Thursday night and into the early morning,” but nothing has changed.
• She asks: Is this doomed to be casual?

Jared’s Advice:

• Not Bitter, But Realistic:

  • He praises the listener for not taking a bitter approach to the casual nature of the hangouts.
  • Recognizes she’s done the “cool girl” move, but it’s reasonable to want more after a month.

  • “Relationships are like sharks. They either keep moving or they die. And this is a very good example of a relationship dying because it’s not moving forward.” (51:03)

• How to Change the Situation:

  • Be direct: Send a text making it clear that the repetitive, only-after-games hangouts aren’t working.
  • Jared’s go-to line:

    “‘Make a plan and I’m in.’ … You turn this vague situation into an on-off switch. He either makes a plan or he doesn’t.” (54:22)

• Making Your Standard Clear:

  • If he doesn’t step up, don’t be afraid to walk away—it’s all about not settling below your value.
  • “Play not to lose,” Jared warns, and you’ll lose; fight for your standards.

• If He Doesn’t Make a Plan:

  • Taste your feelings, see if you’re more annoyed—then break things off respectfully.

  • “I am hoping by the laws of attraction that that enrages you to the point where you go, fuck this dude and you end it. Or he makes a plan and you go and you say, what the hell?” (57:02)

Notable Quotes:

• “I think you need to be a little bit more of a pain in the ass. You’ve been cool.” (58:55)
• “The answer to this is to say, ‘Hey, I’m not going to be at the game this week. … Make a plan, and I’m in.’” (53:00)

Notable Quotes & Memorable Moments

• “Hinge and Uber are the same thing. We’re looking for efficiency.” (32:28)
• “[Chris Rock] is working. He is doing new jokes. He is working through. Not everyone does that.” (07:44)
• “Every amicable breakup was started by one person who wanted to break up more ... There’s no Freaky Friday moment.” (21:32)
• “Taste your feelings … Be turned off. You are turned off.” (53:55)

Timestamps for Important Segments

• Why Mailbag Monday is Valuable: 01:23–04:10
• Chris Rock/Comics & Raw Feedback Rant: 06:30–08:40
• First Email: Hinge and Ex’s Friend: 12:40–43:45
• Breakups & Amicability: 21:30–23:10
• Soft Cancel Text Analysis: 32:00–36:45
• How/When to Follow Up After a Soft Cancel: 40:18–43:45
• Second Email: Volleyball Situationship: 46:15–59:25
• Turning Vague into an On/Off Switch: 54:22
• Being a “Pain in the Ass” and Communicating Needs: 58:55

Episode Tone and Style

• Down-to-earth, conversational, and humorous.
• Equal parts empathy for listeners and frankness about uncomfortable realities.
• Encouragement to be honest with oneself and with partners.

For listeners who haven’t heard the episode:
This episode is a masterclass in practical, candid dating advice for real-world situations: how to handle the awkward aftermath of ex overlap, when to push for what you want, and how to avoid settling for less than you deserve—all delivered in Jared’s signature, relatable style.