You log on to JDate, enter in your most ideal, most specific, most targeted preferences and up pops… that-guy/gal-you’ve-grown-up-with-your-entire-life-who’s-basically-like-family-but-you-aren’t-technically-related. At this point 2 things will go through your mind. First, the “Oh my gosh I can’t believe THIS is my match!? He/She is totally not my type, aside form the fact that we’ve known each other our entire lives, we would never work!” And then, “hmmm… I’ve never thought of him/her that way, I wonder if that would work, JDate seems to think so, could we even go there?”

Proceed with caution. You don’t want to ruin a lifelong friendship and risk awkward family gatherings in the future. But it could be Beshert. Wait til the next holiday when your families get together and then flirt a bit and see what kind of response you get. Drop subtle hints about being single and find out his or her status. If there’s chemistry then it should be obvious. If you’re confident that it’s mutual, then suggest going out for drinks and see where it leads. If things get awkward then back off and save the friendship by changing the conversation to setting each other up on dates.

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