I fell in love with one of my sister's friends. At first, I thought it was just a crush, but it's been a while and the feelings haven't gone away. My sister's other friends know how I feel about this girl and tell me I should say something to her. I'm confused because sometimes she acts as if she likes me too, but other times she totally ignores me. I'm too chicken to ask her out because I don't want to make her feel awkward and put her in a difficult situation (me being her best friend's brother and all). -Should I Tell Her?
Dear Should I Tell Her?,
I can understand how you feel in this situation. One thing to consider is that since her other friends know about how you feel they have probably mentioned something to her. It could be that she also has feelings, but doesn't want to feel awkward about it either. The thing you need to ask yourself is whether the risk is worth the potential reward, or the potential heartbreak? Knowing where you stand one way or the other has got to be better than obsessing and wondering. If you think you love her, or are interested in her, just get her by herself and tell her. If you don't want to make the situation uncomfortable for her, then just ask her out on a date and see how it goes from there. Even if it's only a baby step, it's still a step towards something positive. If you keep both of your best interests at heart, you really can't make a mistake in the way you approach it.