Pining for my Best Friend

Dear Amy,
There is this person who I really like and it just so happens he is my best friend. I really want to go out with him but he doesn’t like me like that. What should I do?

Dear Pining,

      Are you sure he doesn’t like you the same way? The truth is that no matter what happens, it’s probably going to change your relationship with him (at least a little). If you tell him you like him and he doesn’t like you back, it may make things awkward and the friendship may suffer. If you don’t tell him, you’re probably going to find it uncomfortable for a while being around him, which may be ok if you’re more concerned about keeping the friendship. So, what I wonder is, do you know for sure he doesn’t like you that way? Because sometimes, the best relationships are born of being best friends first. Maybe he’s pining for you too?
     My best suggestion is to think carefully about the possible consequences of initiating a relationship with him. If you’ve thought it through, then whatever decision you make, at least you’ll be better equipped to deal with the fallout (good or bad).

Wishing you luck,

Amy