This is sort of a new frontier for me, so any advice would be great. So back over Christmas, I was out with my usual group of friends. Being the holidays and she was visiting, my friends sister came out too. I started talking to her and we hit it off real well. She's really cool, we have a lot (more than most girls I meet) in common and I'm really attracted to her. She's 40 years old (looks 30 at the oldest), has a 24 year old married son living in Florida, Puerto Rican. We've talked a lot She lives in NE Pennsylvania and I live near Pittsburgh. Its 4 hours away, but she runs her own business (event planner), so she said that traveling wouldn't be a problem. We talk all the time on Yahoo while she's in her office and back and forth on Myspace. She prefers younger guys (I'm 26) because of personality reasons. She's been divorced twice (first husband cheated and she rushed into the 2nd (younger guy) and thus mutually decided on a divorce). We've talked about meeting in Atlantic City for a weekend or flying to Florida (I have a friend there) Bottom line is she wants a relationship. She has no problem with the distance and getting together once or twice a month (I'm cool with it too). The oldest woman I've been in a relationship with was two years older than me. I've hooked up with a couple women who were around her age (38, 41). So what is there to know about exploring a relationship with an older woman?