The JTrain Podcast Summary
Host: Jared Freid
Episode: My Boyfriend Won't Spend Christmas With Me! Help! – MONDAY MAILBAG
Date: December 22, 2025

Overview

On this Monday Mailbag episode, comedian Jared Freid offers his trademark honest and comedic advice on listener relationship dilemmas sent in via email. This week, the main themes are navigating the individual versus “we” dynamic in relationships, the courage to act on your feelings, and the tough conversations required as relationships progress—especially around the holidays. The episode covers three detailed listener questions, all revolving around boundaries, vulnerability, and reading intention in dating and relationship contexts.

Key Discussion Points & Insights

1. Should We Step Up Our Date Invites? (00:12–10:54)

Scenario:
A listener shares a creative invite she made for her fifth date with a man—taking the initiative to bring him to a comedy show featuring Jared himself—and wonders if putting so much effort into date invites is “too much.”

Jared’s Take:

• Enthusiastically supports acting on genuine feelings in dating.
• “You did a great thing because you said to this person, I like you so much and I’m so excited about you that I’m going to make this invite...” (05:46)
• Argues there’s no universal law or tribunal dictating how dates have to progress: dating is an “individual sport, like tennis or golf.” (08:15)
• There’s no such thing as “doing too much” if it’s authentic; if it scares someone off, that just provides clarity.
• Counting dates is more often a sign of excitement and sincerity; men may not track as closely, but it’s not inherently a bad thing.

Advice:

• Don’t ask “should we...” in dating; don’t look for permission from the imagined team of singles.
• Vulnerability brings clarity to both parties about intentions and interest.

Notable Moment:
“Dating is an individual sport. It’s singles tennis. It is you, you, you.” – Jared (08:15)

2. My Boyfriend Won’t Spend Christmas With Me (Ad Breaks Skipped) [13:19–22:49]

Scenario:
A woman has been with her boyfriend for 2.5 years, living together in NYC. Despite an otherwise serious relationship, he refuses to spend Christmas together, insisting they each go to their own respective families as usual. She feels rejected, especially as he’s previously been the one pushing for more seriousness.

Jared’s Take:

• Validates her feelings of rejection and concern: “You are not overthinking it. You have been rejected.” (17:22)
• Sees the boyfriend’s refusal as a stalling tactic—indication of reluctance to step into a more committed phase ("next stop on the bus is engagement”).
• Recurring theme: “I" vs. "We” – this is a pivotal moment requiring the boyfriend to make the transition into shared life decisions.
• Warns that holidays, birthdays, and vacations are “tests” in relationships that reveal underlying realities and timelines.

Advice:

• Have an honest, direct conversation before the New Year:
  • Frame it factually (“We have been together 2.5 years and I asked to spend Christmas together…”).
  • Ask open-ended questions: “What were the feelings you had when I asked you…?”, “Do you see us spending next Christmas together?”, “Do you see this going towards engagement or marriage?”
  • Focus first on the holiday issue, then expand out to the relationship future.
• Recognizes the difficulty: “Way harder for you to do. But you’re going to have to sit him down...” (19:30)
• Ultimate advice: Don’t wait indefinitely—seek clarity in timelines and intentions.

Notable Quotes:

• “There is a point... You have to go from I to we to be in a real relationship. Right now, you have tried to make that transition. He has said no.” – Jared (15:17)
• “I feel for both of you. I’ve been him because it’s a reality check.” – Jared (18:37)
• “You were rejected for the holidays. And then bring it outward. Okay, well, what’s next?” – Jared (20:13)

3. Crushing on a Now-Taken Old Acquaintance (Ad Breaks Skipped) [26:16–35:19]

Scenario:
A woman reconnects with a formerly “nice guy,” now “hot, buff, and well-dressed” artist she’s running into frequently. There’s flirtation, but he posts photos with a new girlfriend and introduces her. The listener wonders whether she’s delusional for feeling a vibe and whether she should subtly signal interest.

Jared’s Take:

• Says she isn’t delusional for picking up on real flirtation, but “delusional for seeing this as a romantic ending.”
• Guy’s flirtation is likely only possible because he’s in a relationship and doesn’t face the risk of rejection: “Girlfriend guy gets to be cocky McCockstain and act like a different…” (31:42)
• The guy she sees now is “not necessarily the guy you’d get if he was single.”
• Warns against expecting a movie-style, fateful ending—odds are he simply finds her attractive but will not act.
• “Stay friendly—if he ever becomes single, he’ll pursue if he wants to.”

Advice:

• Don’t initiate. Don’t try to subtly signal. Let it be, focus elsewhere.
• “He is towing the line of flirtation until that point where he goes, ‘Ah, I’ll back away. I got a girlfriend.’” (32:41)
• If they break up and he doesn’t chase you, that’s the answer.
• A romantic storyline is unlikely; the energy is real, but not necessarily meaningful.

Notable Quotes:

• “You’re delusional for thinking that this guy and you are going to be the greatest love that’s ever been known. Because that’s the only way that this works out where you’re happy with it.” – Jared (32:09)
• “The guy you’re interacting with isn’t necessarily the guy that you’re going to end up maybe dating if this rom-com works out.” – Jared (30:40)

Notable Quotes & Moments

• “There’s no messing this up when you do something you feel like doing; this is great.” (05:49)
• “Dating is an individual sport. It’s singles tennis.” (08:15)
• “You are not overthinking it. You have been rejected.” (17:22)
• “Have a sit down... I was hurt that we didn’t do holidays together. You shut it down. Can you give me some background on what made you shut this down?” (19:43)
• “Girlfriend guy gets to be cocky McCockstain and act like a different...” (31:42)
• “You’re intuitive—this guy wants to bang you and probably would if…” (32:18)

Key Timestamps

• Date Invite Discussion: 00:12–10:54
• Boyfriend/Christmas Conundrum: 13:19–22:49
• Crush on Taken Friend: 26:16–35:19

Episode Tone

Jared maintains a supportive but brutally honest approach, weaving humor and personal anecdotes throughout. He values emotional risk-taking and underscores the importance of individual action in dating rather than seeking broader approval.

Summary Takeaways

• Express feelings bravely in dating—there’s no “too much” if it’s real.
• Milestone events (like holidays) are relationship inflection points; if a partner avoids them, a frank discussion is necessary.
• Don’t project fantasy outcomes from flirtation with unavailable people. Reality rarely matches rom-com scripts.
• Dating success is about clarity (not games), individual honesty, and realistic expectations.

Useful for listeners looking for tough, empathetic relationship advice—served with a joke and a nudge toward self-respect.