A
male
age
36-40,
anonymous
writes:Dear Cupid,I am a 22 year old closeted young male who has a crush on a 37 year old gay co-worker. He is nothing more than a friend. I've come out to him a couple months ago and I'm so crazy for him. He's masculine and very fun to be around. I been with other guys and they never compared. He just got out of a messy decade-long relationship and the timing is so wrong. I know he is there mostly for support in my closeted youth, But...How long do I wait to come clean about my feelings for him? Can I come clean with him without destroying our friendship?
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, Isabelle Vane  +, writes (17 June 2009):
Hi there!
First of all, I think you should be sceptical about the idea that there is a 'right' or a 'wrong' time for a relationship. Breakups are all different - sometimes a relationship can be over a long time before it's actually over, so that both parties are ready to move on quite quickly. For instance, a friend of mine had a one night stand with a woman a month after splitting with his longterm girlfriend. At the time, many of his friends thought this was 'just' a rebound, but that one night stand is now his wife, and they have a young baby together. It just happened that she was completely right for him. Like all of the other 'rules' of relationships, the rebound thing isn't set in stone. Human relationships are far more complex than that!
Other times, of course, breakups leave people so devastated that they are left in pain for months, even years, unable to move on. A relationship with an individual in that kind of state is bound to be fraught with difficulties, and will require an astonishing degree of maturity and patience to navigate. The tough task you have is to assess exactly where this guy is emotionally - not at all easy!
If I were you, I would sidestep the issue and let him tell you where he is. In other words, ask him out casually, but in a way that doesn't commit him to anything. Avoid heavy feelings-based conversations ('I love you, you are THE ONE' type stuff) as these pose more of a risk to the friendship if he feels pressured or awkward. Instead, keep it cool, so the ball is in his court. Tell him that you understand that his situation is difficult, but that as and when he is ready to hit the scene again, you would like to go on a date. The key thing to stress is that there's no pressure, and that you're happy for him to take his time until such a moment where he feels comfortable. If you can bear the suspense, tell him he doesn't even have to give you an answer straight away. This way you will hopefully come over as mature, caring and switched on, but interested, so that as and when he does feel able to go out again, you're very much at the top of his queue.
Good luck!
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