The Bert Show – Vault: He Needs Help Telling His Roommate He's In Love

Date: February 17, 2026
Theme: Navigating Love Confessions Between Roommates

Episode Overview

In this episode, The Bert Show team dives into a listener dilemma: Brandon has fallen for his female roommate after two years of living together and wants advice on whether he should confess his feelings – and, crucially, how. The hosts discuss the complexities of shifting from friendship to romance with a roommate, exchanging stories, practical tips, and plenty of laughs along the way.

Key Discussion Points & Insights

1. Brandon’s Situation: Conflicted Feelings

• [02:04] Brandon’s Confession:
  Brandon explains how seeing his roommate behind the scenes led to deeper feelings:
  “Every girl I go out with… I always see myself comparing them to her. I find her attractive...But I'm afraid that I don't want to blow the friendship.”
• He’s unsure if she feels the same and worries about ruining their current relationship.

2. Interpreting Signals: Is She Into Him?

• [02:46] The Team Analyzes Potential Signs
  The team discusses possible signs his roommate might return his feelings:

  • Physical closeness (e.g., cuddling up on the couch, using a shared blanket or pillow)
  • Recurring proximity or opening her door around him
  • Paying attention to appearance (wearing cute pajamas vs. old sweats)
  • Body language, posture, and subtle flirtation

  Notable Quote:
  “Does she sit in cool positions to maybe accentuate her booty? …Good posture means she likes you.” – Jen [03:18]

3. Brandon’s Observations: What Happens Next

• [04:09] Brandon reports new “signs” after paying extra attention:
  • She got him a beer while they watched tv.
  • She put her legs on his lap—a gesture the cast debates as friendly or flirtatious.
    “Well, here's the thing. We're watching tv, and then she stretched out, and she put her legs on my lap.” – Brandon [04:45]
• The group discusses how signs can be ambiguous, especially when deep comfort as friends blurs boundaries.

4. Advice From the Team: Next Steps

Avoid Misreading Signals

• Cautious Observation: Sharia and Jen remind Brandon to avoid over-interpreting friendly actions:
  “Maybe she's gone so far over to the we're just friends side… so I don't know if that one's as clear as we think.” – Jen [05:18]
• Non-Sexual Intimacy: Sharia highlights that comfort is a good sign, but not necessarily romantic:
  “At least there's a comfort level…and a non sexual intimacy level there that's established.” [05:27]

Making The Move: Practical Suggestions

• [05:47] Concrete Assignments:
  Hosts invite listeners to share stories about how they crossed the line from roommates to more.
• [06:13] The Role of Alcohol:
  The team jokes about how chemistry and alcohol tend to spark romantic confessions:
  “It’s like the universal lubricant. Like, it just makes everything go smoother.” – Mike [06:27]

Listener Story: Success From Speaking Up

• [06:41] “Amy” calls in, sharing that she married her roommate and is expecting a child.
  “If he had not have told me, I never would have done it. And so I don’t know what else to say… If he hadn’t told me, I wouldn’t be married right now, and I wouldn’t be extremely happy.” – Amy [08:16]

5. Best Approaches: Not Just a ‘Fake Date’

• [09:00] Ideas for One-on-One Time:

  • The team suggests Brandon create opportunities for extended alone time—a day trip, an event, or an outing that feels “special” without the pressure of a formal date.
  • Jen: “Do like a downtown Atlanta day… lunch and then Braves [game].” [10:26]

• Trap vs. Transparency:
  Mike jokes about tricking her into a date using a work gift card, while Sharia and Jen push back, emphasizing the need for clear intent to avoid confusion.

6. Finding the Right Balance: Subtlety and Directness

• [12:14] Another Listener—Maryanne—Suggests:
  A single-day road trip to Chattanooga or a unique shared experience to set the stage for a meaningful but low-pressure conversation.
  “Take a day on a Saturday and say, let’s go for a short trip…a one day thing.” – Maryanne [12:14]

• Key Takeaway:
  Build an environment where a genuine conversation can happen, but where she can also define her boundaries without awkwardness.

7. Comic Relief: How Not to Make a Move

• [14:07-14:18] Mike and Sharia jokingly exaggerate advice to absurdity:
  “When she comes home from work tonight, be smelling her clothes and that will be a perfect indication that you want the relationship to go a little bit further.” – Mike [14:07]
  “Why don’t you just drop your pants?” – Sharia [14:15]
  The team breaks into laughter, reinforcing the importance of being a little bold—but not that bold.

Notable Quotes & Moments

• On crushing:
  “At first, I think it was more of just a crush…But, man, I really love this girl.” – Brandon [02:04]
• On the ambiguity of friendship vs. romance:
  “So I don't know if that one's as clear as we think.” – Jen [05:18]
• On taking action:
  “If he had not have told me, I never would have done it.” – Amy (listener) [08:16]
• On practical moves:
  “You gotta do something bold. A little bit more, I think, than dinner.” – Bert [12:06]
• On day trips as tests:
  “If a guy asked me to go for a day trip anywhere, your roommate, who you've known for two years, you would still know it was going in that direction.” – Jen [13:41]

Timestamps for Important Segments

• [02:04] – Brandon describes his feelings for his roommate
• [02:46] – The team lists potential signals of romantic interest
• [04:09] – Brandon recounts his recent experiences searching for “signs”
• [06:41] – Listener Amy’s call-in: real-life roommate love story
• [09:00] – Group discusses ideas for subtle yet intimate one-on-one plans
• [12:14] – Listener Maryanne recommends a day trip
• [14:07-14:18] – Comedic escalation: “smelling her clothes” and “drop your pants” banter

Summary: Advice for Brandon and Listeners

The episode blends heartfelt advice and humor as Brandon grapples with confessing his feelings to his roommate. The general consensus is to create shared moments that allow deeper connection—like a unique day out—rather than ambiguous “friends’ dinners” or overt traps. The hosts champion directness with kindness and emphasize that, while there’s no perfect script, making a move with care and authenticity gives love the best shot.

Conclusion:
If you’re in Brandon’s shoes, invite your roommate into a day of shared experiences that naturally allows feelings to surface. Courage paired with respect is the best route—and maybe, just maybe, you'll wind up with your own happy ending (minus any kidnapping or weird clothing maneuvers).