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R.I.P. Elroy Boogie

Popular member of the Kracker Nuttz DJ team was only 27.

Dear Willie D:

I'm a 30-year-old woman who is crazy in love with a guy who has been my best friend since I was a freshman in college. But I don't know how to communicate my desires to him. He is wonderful to talk to. Anytime I'm having a rough day, I can always call him, and even if he's busy, he'll make himself available to accommodate me. I'm not dating anyone at the time, but he is; I just don't know how serious it is because he is clandestine in regards to his dating life.

I have seen two girls he's dated, and they are absolutely gorgeous. Although I don't think I'm gorgeous, I have been told quite often that I'm pretty so I feel as though I have a decent chance with him. I really like him; no, I'm in love with him. But I fear that if I reveal my true feelings, even if they're reciprocated, it will eventually destroy our friendship. What should I do?

Crazy in Love:

Never give up on pursuing a goal before the outcome is decided. Since he's in a relationship, you need to gather intel on how serious it is before you advance. Next time you speak to him, casually ask him how things are going with her. If it's serious, you should give yourself a timetable as to how long you're willing to wait to see how it plays out before you disclose your feelings. If it's not serious, just talk to him as you always do and tell him how you feel.

Relationships don't come with crystal balls. What makes them appealing is excitement and unpredictability. It would be horrible if you guys forged an intimate relationship, broke up and ended up hating each other like many couples do. But that's not the worst thing that could happen. The worst thing that can happen in life is an opportunity unpursued because of fear.

Ask Willie D appears Thursday mornings on Rocks Off.

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