Going from just friends to more
Question:
I’m 27 years old and single. I’ve have a serious crush on my best friend of the opposite sex, but I’m afraid to say something for fear it will ruin our friendship. I’ve had a crush on one of my closest male friends since I met him more than three years ago. He’s 32 now. I’ve watched him date other women with no success, and he always calls me to talk about it when they are having problems or he breaks up. I’d really like to turn this friendship into something romantic. Is that possible? What do I do about this situation? And how do I do it?
Answer:
Does he have a girlfriend at the moment, or expressed an interest in someone new? Has he ever, in all those years, shown any romantic interest in you at all? Those would be two clues to either leave it alone, or cautiously move forward.
If he has no girlfriend or other romantic interest, it would be good to invite him to go with you to a party, an art exhibit, or to play miniature golf or bowl with you – whatever it is you young folks do for fun these days.
I’m going to assume that he enjoys being around you, trusts you, and likes you as a person. However, that doesn’t mean he likes you “like that” and his feelings could be more like sister and brother. However, you’ll never know if you don’t make a move. Two people afraid of rejection and playing it safe means that nothing is ever going to happen unless one of you sucks it up and finds the nerve and courage to take a chance. Risking your friendship should not be a concern, because if you two can’t be friends after you tell him that you are attracted to him, then I’d say you weren’t really friends anyway.
For all you know, he may already be thinking “hey, she’s kinda cute!” but be afraid to say something to you for the same reason you are afraid to approach him! Guys are kinda dense sometimes, so the more of a map and directions to your heart that you can give him, the better off you’ll both be.