Fredrik asked: “I’ve been friends with a girl for quite some years now and we get on really well together. I’ve gone back and forth on how I feel about us being together in a relationship and it seems that I always end up coming back to the idea that we should. At times I’ve gotten the impression that she may feel the same as well. The problem is that we never seem to be single at the same time. I am somewhat recently single and she is not. I like her mate just fine and would never try to come between them but if their relationship were to end at some point, how would you advise I proceed? If a situation were to occur where we were both single, I’d probably only get one shot and I’m not sure what the right move would be. Being that we are friends, would a discussion be proper or awkward? Would it be better to just wait for the right moment and go in for a kiss?”
Liz says: This predicament you’re in is fascinating to me. I’ve never personally experienced a long-time friendship with someone I was actually hot for, nor has a guy friend let so much time pass before making his true feelings known to me. When I first saw the movie When Harry Met Sally, I walked away incredulous that two friends could really be attracted to each other and not recognize that they’re perfect for each other during all those years. Romantic attraction is usually too strong to allow its hosts any chance of keeping it buried for long. Of course, just because I’ve never been in your shoes doesn’t mean it doesn’t happen.
To answer your question, I definitely recommend telling her about your feelings instead of waiting for a good moment to lean in for a kiss. Maybe you could invite her over for an intimate home-cooked meal and let her in on what you really want after pouring some wine and relaxing. If the feelings are mutual, it will be romantic and thoughtful and she will be relieved to hear you finally name the elephant in the room. If she isn’t also into the idea of you two dating, then you will have spared yourself the embarrassment of having tried to kiss her and having her back away surprised.
I agree with you that you should take your “one shot”, and make it count! If you never do, you’ll always wonder, ‘What if?’