New Guy and Past Hookups Situation

[Virago]

Hey everyone, long-time reader but first time poster. I've seen some great advice posted on here so I'm hoping you guys can help me out here.

I'm kind of a shy guy and I've never been in a relationship - mostly through a combination of never wanting to be the initiator and I guess just sheer coincidence that despite the fact that I go to a smaller university in DC with a large gay population, my friends/social groups tend to be straight guys (no real reason other than coincidence as far as I can tell).

Through a combination of being really bad at initiating with guys in a dating/relationshippy way and the fact that I was a typical horny college guy, I had my fair share of hookups. Not a super large amount, but a decent number. Twice during my senior year I had threesomes with 2 pairs of boyfriends because I was curious and wanted try it. (I swear this is relevant haha).

I just graduated in May and ended up meeting a pretty fantastic guy (I'll call him C) via Tinder (for once it actually worked). We've hung out casually a couple times (drinks and such) and I'm trying not to rush anything since I actually really like him and this is the first situation where I had dates that weren't hookups and where I really see it going somewhere. We talk mostly about nerdy academic things intermingled with some shameless flirting haha.

Now the problem:

After C added me on Facebook, naturally I looked through some of his more recent pictures and stuff. And to my shock I come to find out that he is friends with both couples that I had threeways with (everyone here from the couples to C are a couple years older than me and not at my school so I had no idea of their social group). Not only is C friends with them, but he has several pictures with them - they appear to be reasonably close.

I'm not sure what to do in this situation because I feel like either way I'm going to look like a huge slut. And I don't see any way around it being awkward when (in the pretty near future) we do the whole "meet the friends" thing and I wind up in a social situation with the couples, the guy, and myself.

I think I severely underestimated that in DC every gay guy seems to know one another.

What do you guys think I should do? Should just tell the guy before an awkward social situation arises? Do I wait and see if the couples bring it up with me? Do I just not mention it? Is there any way to test the waters/ease into it?

Sorry if these are obvious questions, but this is new territory for me. Any help would be really appreciated.

 

[HunterM]

What makes you think he's not having threeways with those two couples?

 

[Virago]

True, it is possible that he has had/is having threeways with those couples. Definitely can't rule it out.

We've only hung out very casually like twice but from what he has said about these guys (admittedly not a whole lot), he refers to them as friends and they definitely seem to be more "bros" than anything. There's tons of pictures on social media of them doing touristy things around DC. To me it would seem weird to be doing lots of friend-type things with C if he was their threesome buddy. But yeah you make a valid point. If he is indeed doing that then that makes things a lot less awkward (although it may raise an availability issue).

For the sake of me being prepared for all scenarios, what would be your advice on how to proceed assuming he wasn't in any kind of sexual relationship with them?

 

[KaraBulut]

...For the sake of me being prepared for all scenarios, what would be your advice on how to proceed assuming he wasn't in any kind of sexual relationship with them?

Everyone has a past and honestly, it's safe to assume that either he has done a 3-way with them or he knows they do 3-ways.

Right now it's a bit premature- the two of you aren't in any kind of relationship, really. You just met and you're just getting to know each other.

If the relationship continues and you begin dating, you should be honest. You don't have to be specific about the details but you can say something to the effect, "I think I know a couple of your friends. When I was young and naive, I got in over my head with them. I don't want to talk about the details, but I also don't want to lie to you and say that I don't know them."

 

[Virago]

Thank you for the advice!

I totally agree that at this point discussing any sort of past escapades is premature. The only reason I feel compelled to say something soon is because he is fairly close with these guys and hanging out with them (I know it's them since he used their names) was mentioned as a near-future type thing that we would do. So more likely than not, in the next week or so, I will be in a situation in which I am in the same room as all of them at once. And I would kind of rather he hear it from me; as opposed to having to fake not knowing his friends and having them tell him later. (that just sounds like a terrible idea).

So I sort of feel like I'm being compelled to mention it prematurely. Believe me it's something I'd rather not have to say unless we were to actually start dating. But I feel like circumstances (of "meeting" these friends within a week or so) are forcing my hand so to speak.

 

[LuckysRevenge]

Look at it this way. If it's something he is going to judge you for, then he isn't for you anyway.

We all have a past and gay communities outside of huge cities like New York are often very small.

I wouldn't worry. What would you think if you were in his shoes?

 

[sixthson]

1. Own your past

2. Start the relationship on the foundation of truth. Tell him what you told us. He will probably laugh.

 

[Virago]

Absolutely true about him not being worth it if he judges me for it. I think that's something that we all have in the back of our minds; but it really really helps when someone else says it, so thank you.

Yeah I sort of assumed that DC was a large enough city for every gay guy to not know all the others - but clearly I was wrong. I'll chalk that up as a lesson learned haha.

I certainly would not judge anyone for having some hookups, especially in college. However, since all my friends are straight I have never been in the situation of beginning to see someone and then finding out that that someone basically slept with my entire inner friend circle. I honestly don't know what he or anyone would think about that.

At the very least it will be uncomfortable as hell being in a social situation with all of them. It's not at all about me hooking up so much as that through sheer coincidence it happened to be with his closest friends.

You are right, I definitely have to own my past. Normally I have no problem owning it which is why I was so thrown off by a situation that made me uncomfortable about it.

I definitely have to start the potential relationship with the truth. I kind of wanted to wait until he got to know me a bit better but since I'll be seeing the friends fairly soon I guess I just have to suck it up and say something. In theory I suppose he could have shown them my Facebook and they could have already said something. Basically I want to give him as much chance to get to know me before I say something; but I can't really wait if I want to be the one to tell him rather than his friends. Basically I want to have my cake and eat it too, which I know is impossible haha

 

[LuckysRevenge]

I don't think you HAVE to tell him to be honest.
At least not at the outset. That's something personal and if his friends tell him, that would be pretty rude in my opinion.

If it's something that would affect your dating experience and would bother you by keeping it in, go ahead and clear the air.

However, if someone I was dating told me they hooked up with my friend, I would wonder why the hell I needed to know that. Especially if he hasn't introduced you to them yet.

Just my two cents.

 

[Virago]

I definitely see what you are saying. I didn't mean that I would just tell him out of the blue. But once I meet the friends it's either we all pretend that we haven't met before (which I have no idea if that's how they would handle it) or I end up afterward saying "So yeah about your friends..." and hope that I've said it before they did.

I think it would be rude for them to say anything (and in their position, I could not imagine saying anything); but on their end I could totally see them saying something, not meaning it in a negative way but just in an FYI type of way.

Mostly I just don't want to be in a position where I've hung out with all these people at the same time and still didn't tell C about it, knowing that they could bring it up at anytime ans make me look shady for not mentioning it.

Normally I'd feel like it was my solely business and if it was just one friend, I wouldn't see it as an issue. But given that it just happens to be all 4 close friends, I feel like it might look bad if he found out from someone other than me. It's kind of a big coincidence to explain haha.

I can definitely see why someone would think "why would I need to know that?" and that it would be unnecessary /weird to say it. However, I feel like it would be weird if we continued dating and it was learned after like a month of hanging out with him and his friends. A double-edged sword for sure. But thank you, in my state of mind about this, it didn't even occur to me that it might be a bit weird to say until you brought up that point. So thank you.

Sorry, I tend to overthink things. A lot

 

[Craiger]

I'm not sure I understand that, when meeting these friends, you could not acknowledge having met them before. You don't have to go into detail about how you know them. If they want to pursue the where's and when's, leave it up to them. I have a feeling that if they are that close to your friend "C" he probably already knows that they are into threesomes. It does not make you appear to be a "slut" because you happened to experience a threesome during your college days. As was said before, if "C" passes judgement on you for your past, he is not relationship material. You are free to discuss your past to whatever amount of detail you choose. If anything, in my opinion, it puts the couples themselves in the awkward position and it is up to them to explain whatever details they feel necessary. I think you all are going to laugh about this if it is truly aired. Best of luck however you proceed.

Craiger

 

[Virago]

I didn't really have any set plan on the whole acknowledging thing. I was more just trying to lay out that the scenarios are either to acknowledge it or not.

I just assumed that if we acknowledge that we know each other, the inevitable question will be "from where?" or "oh how do you guys know each other?" At that point either 1) we all lie (which I think is pretty dumb in the long term because while obviously I don't have to tell C everything or the details, I'd feel really bad about flat out lying...and if C and I were to start dating down the road, this is not a lie I want hanging over my head). Or 2) we kind of have to just say "Oh we met on Grindr and hooked-up" which is very awkward in a group setting.

I guess I could try to keep it just the two of us and put off the hanging with friends thing for a bit; so when I am faced with it, at least he will know more of my substance and the hookups may not seem as of a big deal a they would on a 1st or 2nd date. The only thing I am certain of is that I want to actually say it to him (and not just have him hear it elsewhere), when it gets to the point that it should be addressed.

He probably knows they are into threeways and from what others have said, him being involved in them with the couples is plausible.

It is a very interesting point you brought up about it being more awkward for the couples and it is up to them to explain what they feel is necessary. That actually made me start to wonder if my telling C about it would be a jerk move since perhaps this may not something the couples want brought up. Maybe what you said about leaving it up to them is the right way to go - see where they are going (whether they are going to be open about it) and if they are, I can just be candid about it and we all sort of just say it at once (since we'd all be in a group setting).

If things work out, we probably will laugh about it down the road haha. But in the present it is mortifying because C and I have been super nerdy/academic/innocently flirty and this hookup thing is like the antithesis of everything else we've bonded over. I'm not trying to be fake or misrepresent myself - but engineering student/consistent-J Crew-wearing/ youthfully-innocent-looking me kind of suggests the opposite of numerous hookups in most people's minds (basically most people assume I'm a huge repressed prude until they get to know me haha).

But yeah, you are right - if C is judgey, then he isn't worth it. I'm just hoping otherwise because I've never had this quick/natural of a connection with someone before.

BTW, Thank you everyone for the replies! I know I keep babbling on; but the responses are really helping me work this out in my mind.

 

[Seasoned]

I'm curious to see how this has progressed. I remember how "the past" was death with by my husband and me and, while sometimes, awkward, it really didn't have much impact.

 

[Virago]

Well, since you asked -

The truth is that it hasn't really progressed much. I decided that I would only say something when the situation came to me (like he shows me a picture of him with his friends on Facebook or I see the friends at some type of social thing with him). Though he mentioned hanging out with his friends on our second date, he hasn't mentioned any doing any sort of social thing with them since. I'm just taking the time to enjoy going on dates with him and being happy with the fact, that when this "past hookups" situation inevitably arises, he will know me a lot better and this one thing won't seem like the big deal that it might have on the first couple of dates when he had little else on which to judge me.

Also, knowing him a little better now, I'm pretty confident that he is not the type of guy to make a big deal out of it. He has been a little insecure about a couple minor things and has opened up about them and I made it clear that I'm not one to judge people for things that are, at the end of the day, unimportant to a relationship.

I'm thinking it will turn out as you said - awkward but with little real impact.