Vault: She's Playing Two Guys at Once and Needs Our Help
The Bert Show
The Bert Show
4.1 • 4.4K Ratings
🗓️ 20 March 2026
⏱️ 10 minutes
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| 0:30.4 | This is the email that came in a couple of days ago. And I think a couple of you guys are going to be in this same situation where you're dating like two different dudes or two different women on Valentine's Day and you're not exactly sure how to handle it. |
| 0:45.1 | So if you've gotten through this process before, unscathed and give us a call and give us some advice here, email reads like this. |
| 0:52.1 | I used to think that this was exactly the type of problem that I would |
| 0:55.6 | want to have, but now I have no idea how to handle it. I'm a completely single, 26 year old |
| 1:01.7 | female in Atlanta, and I'm enjoying the dating scene. I've been dating two guys and really |
| 1:06.8 | enjoying each one of them for completely different reasons. They're polar opposites, and I think that this is why I'm still interested in both guys. |
| 1:14.7 | I've led neither one of them to believe that I am only dating them, and it has never really come up, but I really think that each guy believes that they are the only one. |
| 1:24.2 | Surprisingly, I've had a fairly easy time dating both without any scheduling issues, but as you know, Valentine's Day falls on Saturday this year and both have discussed doing something. |
| 1:34.3 | Uh-oh. |
| 1:34.9 | One has already asked me to dinner and the other one assumes that we will be going out. |
| 1:40.3 | I told guy number one that I would go out to dinner, but I have started to like guy number two a little bit more since then. I've not lied to either guy thus far, and certainly |
| 1:50.1 | do not want to start now. I'm not really ready to break it off with either one, but I don't |
| 1:55.1 | really see a way around it since I will have to tell one that I have other plans on Valentine's |
| 2:00.0 | Day. I thought it might be nice to get some strangers and get some guys' advice also. So how do you handle it? Now, she's already committed to dinner with one. Because the first thought I had is you can somehow see them both on the – because Valentine's Day is 24 hours long, you know, and you don't think so? That's tough. Well, you'd have to make, I think you'd have to make a clear decision on who you want to get, |
| 2:24.7 | who you'd be more comfortable with getting intimate on that day, because that's the second date. |
| 2:29.1 | Well, she's already, I mean, if she's committed to one for dinner, which is what I think her email said, |
| 2:33.5 | guy number one is getting dinner, but guy number two, she likes more. Because you can't really call. And dinner should, dinner should continue on late. Yeah. You can't just end it. So her issue really is, I've committed to dinner with one guy, but I want to be with the other one until... |
| 2:51.0 | But she doesn't want to break it off with either one. |
| 2:52.8 | Right. |
| 2:53.1 | Okay. |
... |
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