I'm a 39 yr. old male and have never been in a serious relationship. This is mainly due to a very low self-image. That has changed. Now I've met this 29 yr. old woman and have very strong feelings about her. She also happens to be my sister’s best friend. Due to the nature of my family, I know my sister would encourage me. The problem is, I don't know if the girl has feelings for me. She has been in very abusive relationships and marriage and also has a 6 yr. old daughter. I simply love the kid to bits. The woman is very outgoing and also has her own small business. I constantly think about her.

We have had moments together, but that was always where somebody else (and wine) was present. We are also continuously cracking jokes at each other. Now, I don't know if it's because I'm her best friends' brother, or because she may actually like me. I hate this not-knowing feeling. It's gotten to a stage where it's actually influencing my lifestyle (for the good, though). I recently lost 100 pounds and I'm also becoming a lot more outgoing. I guess, my question is, how can I be sure she has the same or similar feelings? It's quite difficult for me as I'm also very shy.