I’m in a pickle. I’ve been chatting with this dude every day. We text and talk on the phone because he lives a few states away. When I (34f) first started chatting with him (36m), I expected it to be platonic and casual. I didn’t expect to start falling for him and for us to have spark between us.
The problem is, I lost my virginity to his brother about 14 years ago. His brother and I dated for a few months and I met him a couple times back then, but I really don’t think he remembers me. His brother and I are on good terms. We’ve chatted over the years since we’ve dated, but the spark is gone.
We’re getting closer and closer and I’m thinking about telling him, but I’m not sure how to bring it up or if I even should.
Advice?
28 comments
If you lie now how will you get out when meeting the family and his brother goes I know her we slept together years ago, Imagine how this guy will feel I would be honest explain that you have dated his brother before but now its just plutonic now.
Then he has a chance to digest it just explain how you said it to us that you didnt think you would fall for him if he is mature then he shouldnt care about your past.
Tell him now before it grows. The longer you wait, the bigger the blowup will be. Right now, it might be a midly awkward conversation. Wait till you’re a couple, and it comes out at a family event… hand grenade.
Aaaabsolutely, I can’t believe so many say no 😅😅 it’s gonna come out, and you don’t want it to come out in case the relationship is really good. You gonna pay for that then. Be honest know.
It’s probably good for him to know that you went out with his brother. The specific detail that his brother was your first? Probably doesn’t need to be communicated.
How did you start chatting? If you’ve met before but acted like you hadn’t, that’s already kinda sowing seeds of dishonesty, so I’d try to find a way to mention it. You don’t, however, have any need to get into specifically what you did or didn’t do with the brother, just letting him know you dated should be enough. If he has a problem with it, so be it, but no point lying or just hoping it never comes up.
Yup. ASAP.
Well I’ll just say this. It’s better that you tell him now than him being blindsided by it by his brother at, for instance, a family gathering that he invited you to.
“Hey bro I remember nailing her like 15 years ago and taking her V card!”
“👁️👄👁️”
I don’t think that conversation would go over well at all
I feel like if it starts to turn into something, he kind of deserves to know due to the specifics of the situation. That would be an absolutely devastating thing to find out further down the road, whereas now there is at least a chance it wont be a big deal since you were forthcoming. Understandably it’s not gonna be a fun conversation, but the sooner you tell him the less invested he will be and therefore the easier to process.
Yes, that will also put him off , but tell him for gods sake
As a guy, I’d be pissed if I didn’t know this. So, yea, tell him or tell him it’s not working out.
You absolutely must tell him. Both for his sake and yours. Can you imagine carrying around this lie of omission for years if you guys get more serious? It really wont be that bad. Just be 100% honest and give him a chronology of events and what you said here about sparks.
This is easy. Just mention that you dated his brother briefly a decade and a half ago, and leave it at that. You don’t need to go into the details of your sexual exploits together.
If this develops into a relationship, the longer you wait to tell/remind him about dating the brother, the worse/more awkward that conversation is going to be. Get it over with now. But again, DON’T talk about losing your virginity, etc.
Edit: I meant don’t lead off with “your brother took my virginity.” That’s crazy. If he wants to go into the gory details of your sexual exploits with his brother, so be it. But don’t start there
Gonna find out from you, the brother or possibly a freid of theirs. Should come from you or he might think you tried to hide it from him
You gotta tell someone this or it’s gonna blow up later. Get in front of it.
Tell him now there will be more drama if you get serious and it comes out x
I think, as others have said, telling him you “went out” with his brother is the correct step. He’s going to find out at some point, probably make that as early as possible in a relationship, and let him decide whether or not that is a complete deal breaker for him.
Saying you “lost your virginity to his brother” makes it sound a lot worse, so I would probably not mention that *at all*, it makes it sound like you think it was a really significant event for you, and that you put some kind of emotional weight on it, when it sounds like the exact opposite is true, and is what you are trying to communicate to him.
I wouldn’t be surprised if they already talked. It would best to get it out in the open just in case.
Yeah I’d bring it up sooner rather than later. You have nothing to hide and if you don’t tell him it will appear that you do.
I think it’d be better if you tell him as soon as you can, as in now (very near future).
Otherwise, this situation has the potential to go seriously sideways real fast. Say, think of this possibility: In the future, You and this guy have been together for at least a couple of years. You guys go to a family get together at his parents house. His brother gets drunk and spurts out that he took your virginity. I can’t even imagine how things would go for you after that.
If after hearing that the brother took your virginity, he does not want to continue the relationship, then that’s on him. At least you’ll have good conscience and you won’t have to live your day to day life as if feeling that you are deceiving him somehow.
You have to tell him specially now before things get more serious. He will be the one deciding if it’s a deal breaker or not. It really doesn’t have anything to do with you as you didn’t do anything wrong but ultimately this is crucial information for him to know.
We don’t know either of these guys, but some brothers can be really fucked up and gross with each other, so if you want some control over making sure he finds out in a dignified manner then it better come from you. Oh, and the last thing you want is for you to say something to the brother about keeping it a secret because that will make it look like you might be hiding other things involving the brother.
Some people will be fine with it, some won’t. This isn’t something you can keep secret forever.
Better to have the conversation and see which way he leans.
Believe me, if you don’t tell him, his brother will, and you do not want that, he will take you as untrustworthy. I may be wrong but that is how I would take it if you tried hiding it from me, also if you wait too long, he may leave you asap when he does find out. Be a grown up and let him know.
The brothers might not talk about stuff like this so it’s best that you told him. You can’t just say we dated, you have to say you did the wild thing. I don’t know if you have to go as far as saying you lost your virginity to him. He should know.
Are you insane? 100% you need to tell him. If you don’t that’s a bomb waiting to go off. How would this play out in your mind at family gatherings?
You have to tell him. His brother will 100% tell him and he’ll never forgive you for the embarrassment.
If you don’t tell him soon, this whole thing will blow up in your face at some point.
Personally I don’t think the virginity aspect is especially relevant, but others might feel differently. However, the fact that you dated and had sex, you absolutely must disclose.