Vault: He Needs Help telling His Roommate He's In Love

Summary

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

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

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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.

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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.

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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]

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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

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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).

Transcript

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[Bert]

It Work the Bird Show Brandon called us and he has fallen in love with his roommate.

[Brandon]

So we've been roommates for about two years now. I don't know, I just, I guess because we just spent so much time together and I really get to see who she is behind the scenes. Every girl I go out with, I mean, this girl's great, but I always see myself comparing them to Her. I find her attractive. I guess she finds me attractive, but it's one of those, like, she's always had a boyfriend. And then we just slowly. I just got really. Got to know her, and I was like, man, she really is a cool person. You know, I don't want to be the rebound guy. You know, I feel like if I don't say something, that she's gonna steal her. At first, I think it was more of just a crush because we really just hung out a lot together, and I really got to know her. But, man, I really love this girl. But I'm afraid that I don't want to blow the friendship.

[Amy]

Aww.

[Bert]

So we talked to Brandon a little bit in the Women of the Birch show, and the women in the Birch show community said, look, there are probably things she's been doing over the last couple of years that may give you an indicator if she's into you or not. And some of those, like Wendy said, was if she cuddles up next to you on the couch while you guys are watching a movie, she has a blanket.

[Jen]

Blanket or pillow. Or she leaves her door cracked so you can peek in.

[Mike]

She's flashing here when she's getting changed.

[Bert]

Or using the toilet.

[Amy]

Right.

[Jen]

Does she wear cute pajamas around the house and care about what she looks like, or does she just, like, slop around in old sweats and no makeup?

[Sharia]

Does she posture up?

[Jen]

Does she sit and cool positions to maybe accentuate her booty? I think Melissa said it yesterday. Good posture means she likes you.

[Sharia]

That's right. That's right, man. That if a woman is like, oh, yeah, she's sticking out something for you.

[Jen]

Hey.

[Bert]

Yeah, so we sent Brandon. Just think of the last, you know, like, year, and has she done some of these things, sit around the apartment, see if any of these subtle indicators are there to let him know if he should make a move or not.

[Sharia]

And I was nervous because I thought, can he go home and just be subtle about it and just observe, or is he gonna ask. Ask questions he shouldn't and start saying things he shouldn't say?

[Bert]

Because now he's looking at her through the eyes of somebody that might have a chance. So everything she does is going to be like, yes.

[Sharia]

Yeah, she asked me to go ahead.

[Bert]

And use the remote last night. She loves me. It's a sure sign. Hey, Brandon.

[Brandon]

Hey, guys.

[Bert]

Anything happen? You know, now that you knew what the subtle things were to look for, anything happened that might give you an indicator that, yeah, this. This. There might be a little chance here?

[Brandon]

Well, we Were watching tv, and out of nowhere, she asked if she can get me something. And so she went and got me a beer from the refrigerator.

[Sharia]

Okay.

[Bert]

Anybody?

[Sharia]

Well, she may have been getting up, getting herself something, was just being polite.

[Mike]

Do you think that maybe Wendy's in your head now with all of her subtle signs and everything that she does?

[Brandon]

Yeah, I think my head's still gonna blow up.

[Bert]

Was she sitting close to you on the couch, or were you guys on opposite sides of the couch?

[Brandon]

Well, here's the thing. We're watching tv, and then she stretched out, and she put her legs on my lap.

[Jen]

There you go.

[Mike]

That is a good song, Wendy.

[Brandon]

That.

[Jen]

That's a clear sign.

[Mike]

That's.

[Jen]

I would do that.

[Bert]

She loves you.

[Jen]

Now. Would you also do that with a guy friend? If you felt comfortable enough with that guy friend and you thought, there's no way he's interested in me. There's no way he'll hit on me. Would you put your feet on the side? No, I wouldn't do that to Adam Baum. I don't know.

[Bert]

No.

[Jen]

That'd be awkward.

[Bert]

That's a really good point though, Jen. Like, maybe she's gone so far over to the we're just friends side that she would. She would do that also.

[Jen]

I think I would. Like, if you were just overly comfortable on the friend side, I think I would. So I don't know if that one's as clear as we think.

[Bert]

It's a good one.

[Sharia]

But at least there's a comfort level, you know, and a non sexual intimacy level there that's established. So I still think that, you know, these are signs on how safe it is for you to talk to her, because I do think that you eventually have to tell her how you feel, but at least I think these are signs that she's not going to, you know, kind of reject you harshly.

[Bert]

We need to give him, like, concrete homework assignments. Like, if you have been in this situation before and your roommate turned into your lover and it ended up being a really serious relationship for a very long time, then how did you make that move? It's a difficult thing to travel down because I think in most cases, like, the first time the two you hook up is generally over alcohol.

[Amy]

Mm.

[Sharia]

Yeah.

[Bert]

Like, the chemistry is sort of there, and then it's booze that puts you over the edge. But if you're not gonna go that way, then what do you do?

[Sharia]

That's a great point.

[Bert]

What have you done?

[Sharia]

My friends that were friends before or best friends or whatever, and cross the line it usually was alcohol induced.

[Jen]

Mm.

[Mike]

That's just. It's like the universal lubricant. Like, it just makes everything go smoother.

[Bert]

Everything.

[Mike]

Good morning, Everything.

[Bert]

Oh, we get it. We got it. Amy, you're on Q100. Good morning.

[Amy]

Good morning, guys. How are you?

[Bert]

Good. You have some advice here for Brandon?

[Amy]

Yes. It is just so nice to hear this because it just brings back a lot of old feelings. I went through the same thing. I ended up marrying my roommate. We're expecting our first baby any day now, so congratulations. We have a really good relationship. And I couldn't imagine not have married, not being married to him. And I just love to hear that he's in love with her, and I just want him to go for it so much just because of my good story.

[Bert]

But, well, outside of, like, right off the bat, just sitting her down, going, look, I'm having these feelings for you. What can he do that would give him better insight? Better that this is gonna be okay, or to slowly let her know that this is a direction that it's going in? Ideally, I think the best game plan is doing something that she sort of feels like it's heading down that direction, and if she's not comfortable with it, she can subtly sort of turn him down without really turning him down.

[Sharia]

It doesn't have to be so awkward.

[Bert]

You know what I'm saying?

[Sharia]

But how did it happen? How did it happen with you and your husband?

[Amy]

Well, my situation is totally different. It was actually my roommate's boyfriend that she had brought into to live with us.

[Will]

Oh, damn.

[Jen]

Oh, yeah.

[Amy]

So it's like drama in itself, but as it turned out, he moved out and we ended up dating, and so. And then I got married, so it's, I guess, a little bit different story.

[Jen]

Were you your maid of honor?

[Amy]

No.

[Bert]

Can you give him any advice on what he can do? Tell her no, it's too soon.

[Amy]

If he had not have told me, I never would have done it.

[Mike]

No.

[Amy]

And so I don't know what else to say, because my situation. If he hadn't told me, I wouldn't be married right now, and I wouldn't be extremely happy.

[Jen]

What were the words he used? Like, how did he tell you?

[Amy]

We actually went to a football game at Auburn, and when we got there, we spent a weekend together, just us. And I just saw qualities in him that I was looking for that I never thought about until just me and him were together.

[Bert]

Okay, here's one thing. Here's what I'm taking from that right now. Now it's not an Auburn game. But is there something, Brandon, that you can do with her for a full day where you guys are one on one with each other for a full day? So maybe she'll get the same. Have the same thoughts that this listener.

[Mike]

Had also, like tantric lovemaking. Subtle.

[Jen]

Again, really subtle.

[Bert]

Is there an opportunity to do that?

[Brandon]

What I was thinking was maybe, you know, go out to eat or something, but not asking on a date, but maybe like saying, I want to a gift card from work and say that I gotta use it by this weekend. And if she says good enough, then, you know, maybe she's definitely interested.

[Mike]

So you're almost tricking her into a date.

[Brandon]

Well, I guess that's a good move. But if she says no, then I know she's not interested at all. Right?

[Sharia]

I don't know if that's the right move to make or not. Because even as a friend, if somebody said, hey, I got a gift card and I gotta use it by this week and you want to go, even if it's a good friend of mine, I'd be like, well, why can't you just take me to dinner? But going along, what Bert was saying, is there something to like we talked about how she broke up with her boyfriend or her and her boyfriend broke up. I forgot how long ago it was. And you know, maybe is it an opportunity where he could tell her, you know, let's just get you. I just want to. I don't know how to put this. It can't be a weekend thing because obviously that's too bold. But then I think dinner's too subtle. I think what Bert's saying is right. Like something where you say, I'm just going to take you away, get your mind off of things. You want to go to the blah and be a little more bold than a dinner? I don't think that's bold enough.

[Jen]

I think it's definitely gonna be a daytime activity. Whether they go art museum or something like that aquarium or something. Do like a downtown Atlanta day or something.

[Bert]

Something where you have to interact all.

[Jen]

Day long, lunch and then braves. Cause I know they're in town on Saturday.

[Sharia]

But I think her story about the Auburn thing is somehow they were trapped together. If you go to the aquarium or you go somewhere, she can always say, hey, well, let's take so and so and so and so.

[Mike]

Can you get a friend to take you both hostage and leave you locked in the same room for like 24 hours?

[Bert]

And then the struggle together will bring you tightness.

[Sharia]

I think what Everybody's trying to get to though is there's gotta be something he does where he can get a definitive answer or some clue.

[Mike]

The date, the fake date.

[Sharia]

I don't think that's. I mean, friends go to dinner all the time.

[Mike]

Yeah, but he's saying he's gonna say hey.

[Sharia]

So he's gonna downplay it and say.

[Mike]

Hey, look, I've got a gift card. Do you wanna go to dinner?

[Sharia]

Cause I'm not gonna spend any money on you.

[Mike]

You're creating the trap, right?

[Sharia]

Here's a gift card you're creating.

[Mike]

Hey, hold on. They're poly pessimistic over there. Listen to my story. He' trap like, hey, I've got this gift card. Do you want to go? So now he's not boldly saying he's not asking her on a date. He's inviting her to spend time because of some other circumstance. So he gets her in there, then they have a great dinner and they have a couple drinks at dinner. Universal lubricant, right? Vodka. So they have a couple drinks at dinner, and then he has. That's the perfect opportunity for him or even her to suggest afterwards that they continue their date somewhere else. And by 2am they're making the beast of two backs.

[Sharia]

As roommates, do you two hang out a lot?

[Brandon]

Well, you know, a lot of times we get home from work around the same time. So a lot of times we eat at the apartment, you know, if we have, you know, no plans until later.

[Sharia]

Because some, you know, roommates and some, you know, friends hang out a lot and do things together. I just wondering if going to dinner and hanging out after dinner is unique for you guys.

[Brandon]

I mean, we've done it a couple times.

[Bert]

You gotta do something bold. A little bit more, I think, than dinner. If you guys are doing that and it's not a special night, then there's no indicator here. Hey, Maryanne, good morning. You're on Q100.

[Amy]

Listen, everybody's giving you advice is to let her know what you think about her and that if she reacts this way, you'll know that she's not into you. Well, bottom line is even if she's not quite into you, you don't want to frighten her. She still could get into you. What I'm saying is take a day on a Saturday and say, let's go for a short trip, nothing very long. I would recommend driving to Chattanooga for the day, go up to the aquarium there, have lunch and come back. Just do a one day thing.

[Mike]

Just, you know, that's gonna be a tough sell. Hey, you wanna go to Chattanooga to go to the aquarium?

[Bert]

Well, why don't we just go?

[Mike]

Do you know the biggest one in the world is right there?

[Amy]

No, I'm talking about a trip into Tennessee on a cool day, a nice summer day. And the mountains are beautiful, the drive is beautiful.

[Sharia]

I'm working more on car rides.

[Bert]

Yeah, just something like, you know what.

[Mike]

Let'S get out of here.

[Bert]

Let's just like. Something like, let's just get away from the stress. Let's just go to Chattanooga. I mean, I know it's not a place that we would normally go, but let's just go. Ha.

[Sharia]

Yeah. No, I totally think it has to be something like that. Trapped in the car or, I mean.

[Jen]

I don't know, trapped in the carpet and I'm looking.

[Bert]

Why don't you just kidnap her?

[Jen]

Jeff's like, trap her in when the gifts are due again. Trap her in the car for two.

[Mike]

Hours, put her in a box under your bed and feed her and take her out when you want to play with her.

[Sharia]

But if you're trying to have a non date date, then you got to have her attention somehow. Because if it's.

[Jen]

If a guy asked me to go for a day trip anywhere, your roommate.

[Sharia]

Your roommate, who you've known for two.

[Jen]

Years, you would still know it was going in that direction, which I guess is good because if she says yes, maybe she's into you.

[Bert]

And this could be the subtle. If she says no, then it could be this. You know, it's. She's defining the line without it being uncomfortable.

[Jen]

Because we know when you're trying to get us alone.

[Sharia]

That's the whole point, is for him to find out if she's into him or not. So not to dance around it to where it takes forever and she ends up dating somebody else.

[Mike]

Why don't you just do this? 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.

[Sharia]

Why don't you just drop your pants.

[Bert]

Naked on the couch.

[Podcast Host]

Yeah.

[Mike]

Covering her. Wear her clothes. Take off all your hat. Yes.

[Podcast Host]

The bird show.

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