If you were interested in hooking up with a friend's hot ex girlfriend, and he was cool with it, how would you want him to help you get with her?

[Anonymous]

So I (29m) have an ex girlfriend (25f) who is very attractive and I'm still close friends with (we broke up over 2 years ago). I showed my friend (28m) her photos (just regular ones) and he was very interested. They never met before and he wanted her number. After asking on here about this situation I've decided I should be ok with it and even be supportive of this.

Now I'm wondering exactly how I could help him out while still respecting my ex? I am close with both of them and want the best for both. He does date and hook up with women off dating sites like tinder but doesn't really do relationships so I'm thinking this will most likely be a fling type scenario.

[HollyK21]

If you know he isn’t looking for anything serious then don’t set him up with her. Even if she’s your ex, out of respect you shouldn’t put her in a situation that you know could really hurt her at some point.

[Asker]

That's wise, I really don't want to hurt her... She has some basic experience with hookups, literally just twice, and seemed ok after both times, but I don't want her to get hurt if that's something that's bad for her.

[Asker]

I could probably talk to her about what she's comfortable with first too.

[HollyK21]

Keep in mind that just because she’s had hookups in the past does not mean she went into those situations with the intention for it to be just that. You don’t want to assume she is readily available to be used, and you should want that for her just regardless. If your guy friend is doing fine in the women department and sees her as more of a conquest, then don’t set up your ex for that. If he brings it up again just tell him politely that out of respect for her you don’t think setting them up is the right thing. He’d probably try and convince you of otherwise, but you’ve seen him in action and know his true nature.

[HollyK21]

**shouldn’t want that for her regardless

[Asker]

Yeah last thing I want is for her to get hurt by this, I'll keep that in mind for sure! I should probably discuss this with her before anything happens on my friends end

[HollyK21]

Personally I wouldn’t have that discussion and for a few reasons. For one, if you bring this up to her, then you’d have to be straightforward about the type of guy he is and if she’d be open to a fling. This could be insulting to her, personally I would feel that way, because I’d wonder what about me implies I’m just looking for casual sex, and why you’d try arranging that for me. You couldn’t tell her he’s interested without leaving that part out, and if you did then you’d be lying to her and doing what you don’t want, which is set her up for failure. Lastly, if you were straightforward, I highly doubt she’d be interested, then your friend would (likely) be pissed off that you told her he just wanted sex, even though you both know that’s true. So ultimately if you want to talk, then it’s your choice but I’d stay out of it. Then if they do meet and hit it off, you won’t have to have anything on your conscience when it will likely not work out. Like you weren’t involved in any way.

[Asker]

Yeah you're right here, I really don't think that hooking up is bad but I wouldn't want her to think that's what she's good for.

As far as them meeting, yeah if they click naturally and become fwbs that would be good, or if she convinced him to try a relationship with her I guess that would be the ideal scenario! Thing is their friend groups don't overlap so the only way they'd ever meet is through me somehow, and I'm not sure if that's a good idea with what you've said

And yeah you're right, I don't wanna piss off my friend either, by ruining his chances with her by telling her what his history is, this is very tough lol

[HollyK21]

Very tough indeed! Lol but I don't know at the end of the day, I’m sure you have good intentions and want the best for them both, but in a way he’s not putting you in the best position, which is why friends often stay out of hooking them up with another friend. It just automatically puts you in the middle of a situation between them, and you don’t want you name on (or have to be involved in) any mess, like a broken heart or fall out. Your friend has access to a lot of women, through the apps and surely some he’s met and communicates with regularly. It won’t be the end of the world for him to skip past your ex. It’s nothing personal, of course, and he shouldn’t take it as such.

[Asker]

Yeah you're right lol he has more experience with women than I do for sure! Quite a lot of "conquests" lol

I get what you're saying about putting me in a tough situation... If I knew I could set them up and have them both be satisfied with a good friends with benefits situation I'd consider that a win, I'd feel like a cool friend to him and my ex since it would be quite the experience for her (knowing what he's like), but i definitely need to think of the downsides too

[HollyK21]

I totally get it, like in general I think a lot of people would be hooking up one friend with another if they knew with certainty things would work out, and who knows, your friend could do a whole 360, really shape up for her and be a good boyfriend — thats the ideal outcome lol. But you can’t really base your decision making off hopes and potential when you already have a good idea in real time of what’s in store for your ex. I think it’d be easier to be optimistic if your friend had a better track record but unfortunately he just doesn’t and that’s his own fault for better or worse. How do you think he’s respond if you told him you didn’t want to hook them up? Would you tell him why?

[Asker]

Yeah that's true, he did have a few girlfriends but not any recently, he seems more wild now for sure lol

I would tell him why I'm not going to help him if he keeps pressing me, which he did already lol maybe that'll give him a chance to defend himself and maybe he is kind of wanting a relationship now and isn't aiming to just get in her pants? Who knows lol I think part of the reason he is interested might be because her and I dated and he's curious about the kind of girl I was with

[HollyK21]

Maybe that’s the better route, like to chat with him and explain your concerns. He couldn’t be offended because I mean it is what it is lol but you could just tell him she’s a really good girl and you don’t want her getting hurt. Ask him to keep it real about his intentions and if they’re convincingly good, make sure he knows that if he screws her over there’s going to be a problem. You’ve got to have her back in this, you know what I mean?

[Asker]

You're right, it would be good to make it clear he has to be very respectful here and want something that has meaning! I would definitely have her back in this situation, she will obviously find out he's very experienced if they start getting close because he'll know how to take care of her lol I do think it'd be really interesting hearing about what's happening from both sides if they start seeing one another, I could probably offer both of them lots of advice and I think she'd be a very happy woman if things worked out

[HollyK21]

I agree 100%, he’d have to want something with meaning and have good intentions, otherwise I would just shut that down if I were you lol. If he does have good intentions, then present it to her, give him her number and let it play out. I genuinely wouldn’t get too involved from there though. Remember, it would be two people building a bond, so there doesn’t need to be a middle man coaching them along the way. Especially since you’re both of their friend, it could really backfire giving advice to one that the other doesn’t agree with. You’d have to be extremely unbiased, which would be hard if let’s say one is very wrong and the other is right, or things of that nature. I’m sure you have a lot happening in your life, and don’t need to be responsible for any additional situations.

[Asker]

Yeah you're right, I doubt he needs a lot of help and she probably would enjoy being chased lol and yeah I don't want to lose either of them! And if something bad happens I'll just take her side

It seems like this is a very solid plan lol besides I think he'll get more out of a relationship with her then just a fwbs situation and I think she'd be more comfortable in a relationship too

[HollyK21]

That would be ideal! Lol I am a firm believer that every “playboy” meets a woman who could make him change his ways. Maybe she could be that for him but who knows.

[Asker]

Oh yeah for sure!! She has an amazing personality and is very caring and sensitive and I feel like he'd appreciate that a lot, he is kinda emotional too even, he's kinda like a combination of a jock and musician lol

Also it might be weird to say but from what I know about both I think they'd be very compatible in bed, she acts innocent and is a little shy but she has a high drive and can be wild in person and I know he could show her a lot of new things she hasn't experienced before, hope that isn't tmi

[HollyK21]

Nope that’s not tmi lol well hey opposites attract so judging by what you say they can be very compatible! One step at a time though lol hopefully the conversation you have with him satisfies enough to even give him the opportunity to date her.

[Asker]

I know he's kinda dominant and rough with girls in bed though, so it'd be a different experience for her!

Yeah you're spot on, I really hope he is okay with the terms of actually being serious with her... It'd be interesting seeing their chemistry develop over time and seeing her put on her best for him

[HollyK21]

Assuming he does the right thing lol let’s hope so. If he doesn’t then it’s good to know you’ll have her back!

[Asker]

Lol yes! I think he'd actually have a better sex life with her as his girlfriend than a friends with benefits too and I'm gonna straight up say that, because she values a deep connection and she will make sure her man is happy, and I'll also tell him she's a great girlfriend in general

It's gonna be a little weird introducing them and basically being like "he's going to be taking the position I once had" but she's been single for too long lol I really want to see her happy

[maximumpower]

Compare notes.
Be sure that you're sincere in wanting to hook up.
If she knows you're already in on the information, then she'll likely be skeptical.

[Asker]

Yeah I think I'll see what my friends intentions are and stay out of their way as much as possible to not piss off anyone, but take her side if he messes it all up lol