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Would you do this?

My little sister's best friend broke up with her boyfriend last night. I have a guy friend that I've stayed close with since high school. We never dated or anything, we just keep in touch. Just this morning, he tells me he saw on Facebook that K and her boyfriend broke up, and then says "I've always liked her". I did a double take- I'm 6 years older than my sister's friend, who is 18...which would make him almost 8 years older than her. He wants me to basically play matchmaker. I know his reputation with girls is not very brag-worthy, to say the least. It puts me in a rough position because I know how lonely he is... but if he ever would hurt her, I would probably cause him some intense physical pain, if you know what I'm saying. What would you do? I should add... I can't just bow out gracefully because his only route to my sister's friend is through me.

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SAHMomOf3

Asked by SAHMomOf3 at 1:42 PM on Oct. 22, 2010 in Relationships

Level 17 (3,874 Credits)
Answers (26)
  • I wouldn't. Especially if you know his dating track-record isn't well. Besides, being 8 years older than an 18 year old is just akward.
    AtHomeMommy-3

    Answer by AtHomeMommy-3 at 1:44 PM on Oct. 22, 2010

  • I would ask the lady in question is she wants to connect, if she does I would, you never know you might be connecting romance..............
    older

    Answer by older at 1:44 PM on Oct. 22, 2010

  • I would tell him to message her himself if he is interested. Personally, I wouldnt. & I think 8 years is a bit much considering she is only 18. Just tell him if hes interested to contact her via FB or whatever himself. GL.
    xxMasonsMommaxx

    Answer by xxMasonsMommaxx at 1:46 PM on Oct. 22, 2010

  • That is a hard question. Do you think they would be compatible at all? Or is this just more of a conquest for him? I think if she just broke up with her boyfriend she probably isn't ready to move on quite yet anyways. Just give it some time. It will play itself out.
    AdoreMaFamille

    Answer by AdoreMaFamille at 1:48 PM on Oct. 22, 2010

  • If you really don't want to be a part of it, just tell him that. I don't like playing matchmaker and I tell my friends that all the time. There was only one exception, and that was because I knew they were perfect for each other. Everyone else has to make a match on their own. If he want to hook up with her, have them over at the same time and let them try to work it out.

    krissyvelazquez

    Answer by krissyvelazquez at 1:48 PM on Oct. 22, 2010

  • if you are that close tell him too bad because of his rep you won't do it.. period..
    maxsmom11807

    Answer by maxsmom11807 at 1:48 PM on Oct. 22, 2010

  • I would not play matchmaker or middle man. If he wants to meet with her, he needs to IM her or otherwise contact her. That leaves you out if anything goes wrong.

    A true friend will not put you in that type of position.
    Jademom07

    Answer by Jademom07 at 1:48 PM on Oct. 22, 2010

  • Wow thats kinda weird. I just dont see why a man would want someone so much younger then him. I mean if she was like 21 ok maybe but she can not even go out and get a drink with this guy. To each his own I guess!
    If you say something to K but I would be very upfront with her. I would make sure to tell her that his track record with woman has not been all that great. I'm not into throwing people under the bus but I would not want this girl going into a situation with blinders on.
    Could you just say to your guy friend ~eeewww I am not going to hook you up with my little sisters best friend?!??! lol
    Good luck with that it is an akward situation to be in.
    mommyof3COJ

    Answer by mommyof3COJ at 1:51 PM on Oct. 22, 2010

  • You aren't his only route to this girl...if he wants her he can walk up to her himself. He needs no other connection other than that he likes her. He shouldn't put you in such an awkward position.
    an-apple-a-day

    Answer by an-apple-a-day at 1:51 PM on Oct. 22, 2010

  • I would say to her in a very casual way "hey you know who asked about your status? He's interested", see what her response is to that, if she asks you about him and just say well maybe you guys should just hang out see where it goes. She may not even be interested in him at all and you can just tell your friend you put it out there tell him if he's interested further he should contact her himself. I don't necessarily think that this approach leads you to you putting your approval seal on it, it's putting it out there but leaving it out to them to contact the other if they are interested. good luck!
    LuvmyFam6

    Answer by LuvmyFam6 at 1:53 PM on Oct. 22, 2010

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