Episode Overview

Episode Title: Do I Have To Invite My Boss To My Wedding? – MONDAY MAILBAG
Podcast: The JTrain Podcast
Host: Jared Freid
Date: September 29, 2025

This special work-themed Mailbag Monday episode sees comedian Jared Freid answering listener questions about workplace dilemmas, boundaries, and the sometimes messy overlap between personal and professional life. Jared provides insightful, honest, and comedic advice to three work-related listener emails, covering topics from wedding guest list politics to workplace flirtations and dating colleagues.

Key Discussion Points & Insights

1. The Boss at My Wedding? (00:10–22:25)

Email Summary:

A listener, recently engaged, struggles with whether to invite her boss to her 100-person wedding after her boss assumed an invite.

Jared’s Breakdown:

• On the Guest List Dilemma:
  Jared begins by normalizing the stress around wedding guest lists, especially with limited space:

  “Everyone has this problem... it’s something that makes me go, oh good, I’m not a fucking idiot. I’m not a loser.” [07:45]

• Work Invite Breakdown:
  He humorously narrates how fast 100 guests get claimed by family, obligatory invites, and now, work people.

• On Obligation vs Benefit:
  Jared insists there’s no obligation to invite work colleagues, but acknowledges there are pros/cons:

  “You don’t have to do anything you don’t want to do. There are consequences. There are pros and cons to all decisions.” [14:10]

• On Bosses Who Assume Invites:
  He calls out the boss’s entitled behavior:

  “Who’s excited to receive a save the date? What kind of loser... is sitting at home waiting by the mailbox?” [12:49]
  Jared jokes how out of line it is for a boss to expect to be invited after less than a year.

• The ‘Marketing Opportunity’ Angle:
  Jared frames it as a potential opportunity:

  “As far as marketing is concerned, the marketing of you, I think you are better off for having your boss at the wedding than you are for having them not at the wedding.” [19:55]

• No Domino Effect:
  If you do invite your boss, Jared notes you’re not automatically required to invite all colleagues:

  “I think you can go boss on their own. Done. If you want.” [21:54]

Key Takeaways:

• Normalize the struggle—everyone fights about the guest list.
• No obligation to invite the boss, but it may help your standing.
• Only weigh the boss vs. the next least essential guest.
• One work invite doesn't require inviting the whole office.

2. Workplace Flirtation and Friendship Boundaries (24:49–38:30)

Email Summary:

A young woman, new in town, wonders if she’s overreacting after workplace friendship with a male colleague turns uncomfortable due to his unwanted flirting and sexual comments.

Jared’s Breakdown:

• Can Straight Men and Women Be Friends? Jared empathizes with the confusion and disappointment when friendly banter is misinterpreted, and stresses clear boundaries are necessary:

  “When you say I’m looking for friends, he’s not the friend. He’s not looking for friends.” [26:20]

• Communication & Boundaries:
  He voices sympathy for how hard it is to assert clear boundaries, especially for younger people:

  “Why do I have to end something with someone that I’ve never began with? That sucks. I hate that.” [31:16]

  Jared prescribes a direct cutoff, with kindness:

  “We need to take a minute to let this cool, because I don’t want the same thing as you.” [29:12]

• Societal Narratives = Distraction:
  Jared warns against generalizing:

  “You’re not going to solve society. ...You want friends, so let’s go make them with people who want to be them. Now, if you come across a guy in the future who’s trying to be your friend... that is a sad reality you have to keep in mind.” [36:00]

• Direct Advice:
  Jared suggests proactively ending the personal relationship:

  “Hey, I really appreciated the relationship... It was a friendship to me... I need to stop texting with you and I hope you can respect this boundary.” [35:41]

Key Takeaways:

• If signals consistently don’t match, cut things off clearly and kindly.
• You can’t “fix” power or gender dynamics alone; focus on your happiness.
• Don’t get distracted by “men and women can’t be friends” debates—just seek true friends.
• Be direct but cordial at work; energy is better spent making genuine connections.

3. Should I Ask Out a Coworker I Might Soon Supervise? (43:40–53:15)

Email Summary:

A 30-year-old woman is considering asking out a coworker she likes, but is also applying for a promotion that could make her this woman’s supervisor.

Jared’s Breakdown:

• Cross the Bridge When You Get There:
  Jared gently urges not to overthink hypothetical problems:

  “These two things happening are happening... At some point those roads are going to cross. They haven’t yet. I think when they do cross, you’re a mature person... Why would this situation, if it happens, be any different than that?” [45:05]

• On Taking (Calculated) Risks:
  He calls it “woo-woo” but champions optimism:

  “What if you had everything you wanted? The woman of your dreams, the job of your life? ...You know how that doesn’t happen? If you don’t try.” [46:32]

• "PEMDAS" of Office Romance:
  Only worry about policy and conflicts if you have both the relationship and the supervisor role.

• Clear, Communicative Approach:
  If both things happen, suggest radical honesty—with HR and the coworker.

• Signature Jared-ism:

  “If you wrote to me and said, ‘I’m the supervisor of a hot broad I’m trying to bang,’ I would be like, ‘Hey, you are in trouble. Back it up.’ But that’s not what you wrote.” [48:55]

Key Takeaways:

• Don’t preemptively forfeit opportunities based on “what ifs.”
• Pursue personal and professional goals; handle conflicts if/when they materialize.
• Prioritize open communication if both a relationship and a power differential emerge.
• The “order of operations” (PEMDAS) matters—don’t overcomplicate before there’s an issue.

Notable Quotes & Moments

• On Weddings and Obligations (Jared, 13:00):
  “Who wants to go to a wedding of someone they kind of half know? Those are crazy. That’s a crazy person.”

• On Boundaries at Work (Jared, 32:58):
  “This sucks that you have to interact with him at work, but this is one of those things where I think you gotta dump him. Even though there’s nothing. There’s never been a relationship. A dumping has to happen because he’s not even listening to you.”

• On Optimism in Office Romance (Jared, 46:32):
  “What if you had everything you wanted? The woman of your dreams, the job of your life? Wouldn’t it be great?... You know how that doesn’t happen? If you don’t try.”

• On Cutting Off Wasted Energy (Jared, 37:27):
  “I think your time will be better spent worrying about you rather than why men and women can’t be friends without sex being involved, because they can. It’s just hard to find.”

Timestamps for Important Segments

• Episode Start & Theme Explanation: 00:00–03:51
• Main Question 1: Boss at My Wedding: 07:30–22:25
• Main Question 2: Workplace Friend-Flirt Boundaries: 24:49–38:30
• Main Question 3: Should I Ask Out a Potential Subordinate?: 43:40–53:15

Tone & Style

Jared’s approach remains self-effacing, direct, and highly relatable, often weaving in personal anecdotes and playful asides. He balances humor with empathy, especially when giving “tough love” on workplace hierarchies and the realities of adult boundaries.

In Summary

This episode of the JTrain Podcast combines relatable advice with comic candor as Jared Freid tackles three distinct workplace dilemmas. Listeners walk away with actionable frameworks, permission to set boundaries, and a reminder that sometimes, the best thing you can do is to try—whether that’s inviting the boss, shutting down a flirt, or shooting your shot at love and promotion alike.