Should I risk opening connections with a guy I personally find annoying in order to set him up with my friend?
There's a guy. Let's call him John. John apparently had a big crush on me in high school and decided to friend me on Facebook about 6 years later and tell me. He has indicated interest in me now, I have told him I am not interested, and he rescinded his interest. Now he says he only ever wanted to be friends, but does not seem to get the (sometimes very blatant) hint that I do not want to be friends with him. I find him highly annoying and make no attempt to disguise this. He very frequently IMs me on Facebook just to say "hey" and then "what's up" (if I respond) without actually having anything further to discuss after that point. I am thisclose to just removing his ass from my friend list and telling him to never contact me again. However, I have this other good friend who we will call Debbie. Debbie is not an unattractive girl but she is what some people might also find to be somewhat annoying. I suspect I am her only good friend because she clings to me desperately in social situations and seems to rely entirely upon me in order to even have a social life. She could also really use a guy in her life, as she has low self esteem and is very shy with guys and I think it might give her some confidence to have some male attention for a little while. Also, for the love of god, the woman needs to get laid. So obviously it has occurred to me that I might be able to fix these two up. John would be off my back if he takes to Debbie, and Debbie would be a bit happier if the two of them hit it off. The problem is that I'm unsure as to how to go about this. It seems to me that the best, most polite thing to do would be to invite both of them out and introduce them in person. (A friend or two said I should just give them each other's contact info but that seems unclassy to me and I feel that would make it uncomfortable for her because she is quite shy.) But if it's just me and the two of them, I foresee him forgetting which of us he's with, and her shyly fading into the background, leaving him to think he is on a date with me! (Or even that I invited him as MY friend because I WANT to hang out with him.) There was another guy I was hoping I might be able to invite for myself by this point but that didn't exactly work out for me. There's another guy I'm currently scoping but I don't know how that's going to turn out either. So, should I just buck up and invite the two of them out with me and endure what will undoubtedly be an awkward situation for myself, or should I wait until I can invite a guy to hang out with ME leaving the two of them together? Or should I just invite another girl friend and tell her to stick with me? The other problem is that if I invite John I fear he will take that as some warped sign that I have some interest in him. In fact when I suggested that he might hit it off with my friend (when he was hitting on me) he was all, "OMG you really DO want to be friends with me, I'm so happy!!" I've already told him off in the past (and very bluntly told him I do NOT want to be friends) and yet he continued to IM me, sure that I would "come around" eventually and now he thinks I want to be friends. I do not want this guy to think I have any interest in a personal friendship with him but it could turn out to be a good thing for Debbie.
Etiquette - 1 Answers
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1 :
I only read your initial question and will advise you not to play matchmaker. If usually ends in disaster. And judging by the length of your question, you don't need anymore problems.
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