I wrote this up for a younger guy who was asking about how to "woo" older women. And I thought I'd post it here just for giggles.
How you approach an older woman really depends on what type of relationship you're looking for, and how you present yourself. Young guys tend to be very sex-focused, and there are going to be a few women who want a purely sexual relationship and that's it. If that's what you're looking for, then if you present yourself that way, those women will respond.
If you're looking for a more serious relationship, keep a few things in mind. First, you're handicapped by your age, and all the other guys your age who've probably hit on this woman solely because she's more sexually experienced and comfortable with herself. If she wants a relationship that includes companionship, she's not going to take you seriously because she pretty much assumes a guy your age only wants sex.
You're going to have to approach her on a companionship basis. Try to forge a friendship. Show her that you have things in common, that she'll enjoy hanging out with you. That you're interested in companionship as well as sex. That you can speak her language. Many women are going to respond to your youthful energy, but they worry that your interests are going to be too disparate... that you aren't going to enjoy the same sorts of things that she does. That you're going to want to be out partying, or whatever, and maybe she likes a bit of that, but also likes to hang out at home, cuddling and watching a movie, going to the theater, or playing mini-golf.
Women generally are more interested in companionship in their relationships. They want to enjoy the company of the guy outside of bed. If you can prove that you can BE that companion, and that she'll enjoy your company, then you'll probably get an "in."
I tend to lean towards younger guys because it's more likely that I'll share some of their interests, and that they'll be more comfortable with my job and my internet dependency. (Plus, most guys my age who are interested in me are damaged, playboys, married, or REALLY incompatible.) In fact, I dated a much younger guy for awhile, simply because we did start out on a friendship basis. We had fun together, just hanging out, watching movies, playing video games, going out for dinner. We talked about lots of things, and shared common interests like musical theater. The sex came later.
