I've known this girl for almost 2 years now. She dated one of my best friends a little over 2 years ago. He has always told me he doesn't care about her at all and is aware thy we do talk occasionally. Just up until now, she came back into my life and we have been hanging out a lot lately. I've always kept her in the back of my head, but at this point in life her and I are both in a position where we could use someone and a steady relationship. Honestly things seem like they would be perfect if we were together.

I would like to know how I should go about telling her how I feel about her, and if that would even be a good idea given the fact that she did date my best friend years back. I feel as if she would welcome my feelings as something good, but at the same time I feel hesitant about the situation.

Just let her know that you like her. You can slip that you like her into a conversation. Then see her reaction, if she admits to like you back, go ahead the way is clear!