I've been good friends with a guy 19 years older than I am for almost 5 years now. We recently took our relationship to the next level since we were both single, but not without much debate and discussion as to whether or not it's the appropriate thing to do given our age difference. We were concerned about how our friendship would be affected by sex, and so far we've become even closer than before. Can't go a day without talking to each other now. It's a great feeling being in a relationship where the guy genuinely shows human interest in you, yet also makes you feel sexy without actually making you feel nothing more than a piece of ass! He's 44 and I'm 25.