From a true blue friend:
Joe,
I have a friend who is 32 years old but so shy
and workholic that he has never dated a girl. He has lots
of good qualities hidden inside, like honesty, sincerity,
dependability etc, but has no surface sheen whatsoever, so
most girls overlook him. He likes me a lot, and
probably more than just liking. But I believe that he
will be happier with one of my girlfriends, a very
nice girl,on a long term basis. I introduced him to her, but he
didn't show any interest. If I force him, he might feel wrongly
that I don't like him anymore. Could you help me find
a way to gently turn his attention to her ? thank you.
Once upon a time, some people said to Christopher Columbus: "Chris, it's impossible to sail around the world, it's flat!", but Christopher was not dissuaded from his idea of finding the Orient by sailing west from Spain. He took on this impossible task, and, well, did not succeed. He didn't get anywhere near the Orient. He stumbled across a little chunk of land sticking in his way called the Americas. But good ol' Chris didn't care, he just pretended he had reached his destination. Then he and his crew promptly infected the local population with diseases their immune system had no defense from, killed them with weapons they had never imagined existed, and enslaved them, starting a tragic mistreatment of an entire hemisphere's original inhabitiants whose effects can be seen and felt to this day.
Like Christopher Columbus, you too face an impossible task, one that maybe shouldn't be undertaken. You may mean well, but your actions have the potential to cause untold suffering and pain. If your female friend likes this guy, she should go after him, it's not really any of your business. If you're just trying to set them up because they're both equally pathetic in their inability to get dates, I hereby order you to lash yourself with a wet noodle 100 times for thinking about meddling in affairs that not invited into. If you try to force the issue, you'll wind up with a serious mess on your hands, and probably lose most of your friends in the process.
Here's what happens:
You: Bob, don't you think Sarah looks cute tonight?
Bob: Uh, I didn't notice.
You: Sarah, you and Bob have something in common, you both love Hummel Figurines!
Sarah: Oh. That's nice. Is Brad here yet?
You: Bob, why don't you ask Sarah to dance?
Bob: Because I don't want to.
Sarah: I'm going to go call Brad's apartment.
Bob: Why are you pushing me toward Sarah?
You: Oh, no reason.
Bob: You're trying to divert my affections for you onto someone else, because my feelings
make you uncomfortable! You wench! I'm going to Vegas to drink myself to death!
Sarah: You put on really shitty parties, I'm going to Brad's to get laid.
You: Wait, I didn't mean for this to happen! Don't go!
Bob's family blames you for his death, and throws dirt on you when you try to attend his funeral. Sarah is deeply insulted by your matchmaking, thinking that you think she'd be perfect for a suicidal dork like Bob. She never talks to you again. The end.
Joe

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