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How can I get my ex and my best friend together without meddling too much?

Tagged as: Dating, Friends, Teenage, The ex-factor<< Previous question   Next question >>
Question - (4 January 2011) 1 Answers - (Newest, 4 January 2011)
A male United States age 26-29, *rns96 writes:

My best friend in the whole freaking world is being an idiot. :D I say that as affectionately as I can, though there is definitely an undertone of frustration.

We are freshmans, and you know, highschool drama and all that. I broke up with Dana a while ago, and JP (my best buddy) has had a crush on her for EVER.

I told him I wouldn't mind if he dated her, I have tried multiple times to get him to flirt with her. He talks to her just fine, but when she flirts, he freezes up and can't think of anything witty to say.

Dana's talked to me about it (we're still very great friends [thank God, I don't know what I'd do without her]) and she said she finds this adorable.

I don't want to tell Dana of JP's feelings, and vice versa. I'd rather not be accused of meddling. All JP realky needs to do is go out of his way to show her he cares about her.

However, he is terribly shy and lacks self confidence in an extreme way. He complains to me incessantly:

"Do you see how you get a hug whenever you see her, and I get a simple 'hi'?"

"Dana's not interesed in me, there's no way."

"I think she still likes you."

If getting them together stops JP's self deprecating remarks in my ear, makes Dana happy, and makes JP happy,I need to get them together.

Don't get me wrong, I love the guy, but when someone is constantly telling you how much he sucks, and you know for a fact it's not true, it irritates the hell out of you.

How can I tactfully get them together, without coming on to the idea too strongly and inadverdently ruining the potential for relationship? Or am I wrong for my efforts?

View related questions: best friend, broke up, confidence, crush, flirt, my ex, shy

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A male reader, Welsh Uncle Dave United Kingdom +, writes (4 January 2011):

I think you need to give both of them a nudge in the right direction.

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