My friend wants me to try and set him up with my ex because he set me up with someone once, what should I do?

[Anonymous]

I showed my friend my ex's Facebook pictures one night when we discussed women, and he seemed very interested. I didn't think much of it, she's an attractive woman and we are still really close.

Later he set me up for a date with this lady, but nothing really ended up happening, now he wants to get with my ex. He doesn't do relationships, just flings and hookups.

He's saying I should do him the favor cause he did it for me and would do it again.

Should I even approach my ex about this? Should I try to help him?

[Anonymous]

If he’s not a good guy then no, don’t get her mixed up in that. If he’s upset about it then oh well. So what if he hooked you up once I’m sure the woman isn’t someone he cares about as much as you do for your ex. It’s like looking out for a good friend, she deserves that much.

[Asker]

He is fun and nice, he has a lot of friends and women really like him, so it's hard to say if he's good or bad

Is he bad for wanting to sleep with her?

I care about both him and her, I want both of them to be happy, but I'll be prioritizing my ex here, I just don't know if this would be a super bad arrangement for her

[Opinion Owner]

You said he does flings and hookups, so he would do the same for her. It wouldn’t even bring it up to her, don’t say anything to him either unless he asks again.

[Asker]

Alright that's smart, I'll tell him off if he asks again

[Opinion Owner]

Yep! Or just keep it simple, tell him she’s not available and you don’t know much else about it

[Asker]

Yeah, he might try something on his own though, like add her on FB or talk to her when I take her out for a group hangout, he's good at this kind of thing

[Opinion Owner]

If you were to tell him she’s seeing someone it would be really grimey of him to still reach out to her, but at that point it’s out of your hands. Since you said you’re good friends with her, Im sure she would tell you he reached out and ask your thoughts, then that’s your window to warn her. But aside from that I say let it play out. You’re doing your part by not being the bridge that connects them but you can’t control if they find each other on their own.

[Asker]

I see what you're saying, it would probably stop him from pursuing her right away but he'd eventually talk to her, and she might be upset I lied about her instead of talking to her, but this approach is safe

IF he talks to her and she discusses it with me I'll tell her everything about him and leave nothing out so that she can decide for herself

If they decide to become friends with benefits I think I'd feel weird but I'm also mature enough to handle it, as their friend I'd try to be supportive but I'd be on her side over his if something happens, he'd be held accountable by me for sure if he hurt her somehow

[Opinion Owner]

Well, I can’t speak for her of course but if I were in her position I’d be more grateful than anything. Nothing would make me feel good about being hooked up with a guy that my friend knew was a player, so I wouldn’t worry about that if I were you. I also think it’s great that you’re ultimately willing to look out for her should they cross paths☺️

[Asker]

I'm really wondering if she'd go for it or not cause he's good at coming across as super friendly and good to be around, he has charisma and that's why he's popular on dating sites, but he also brags about being rough and stuff, like spanking and hair pulling and choking, and I've NEVER done that with her, I was always gentle, but yeah I'll do what you said and hope for the best, and then look out for her if it happens

[DizzyDesii]

A true friend wouldn't ask to get with your ex. I’d never trust that person again

[Asker]

It took me off guard for sure! And he knows we're still friends too

[DizzyDesii]

The fact he hooked you up with someone then asked this, just goes to show that it was always apart of his plan. he's not a true friend who does things from the good of his heart. He expects something in return and something he knows he should never have at that

[Asker]

You're absolutely right, he probably planned this out, I'm gonna tell him she isn't available but I'm thinking he's going to try to get in touch with her by adding her on FB or approaching her if I take her out to a group hangout

[DizzyDesii]

Make sure you also ask him “what kind of friend would try to get with my ex”

[Asker]

That's a good thing to ask him

I'm thinking if they become friends with benefits I'll try to be cool with the situation while it lasts, and I'll be taking her side if things don't go well obviously, and this is cause I don't know how she'll respond to his advances, he's pretty popular with the ladies so he might actually win her over

[Adam1978]

No you don't hookup your friends with other friends. If you know it's not a mutual good match. Your friend needs to find his pussy elsewhere.

[Asker]

Yeah that's pretty much what he wants here

[BlackJeep]

Hell no. If he sleeps with her she's going to compare him to you. Nothing good can come of that

[Asker]

That's what I'm thinking too, him and I are very different, he's been with more women, so more experienced for sure, he's always hooking up, it could be a bit awkward for me