He's got 20 years on you, but you find him irresistible. You'd love to date him, but how? Flirting with an older man is similar to flirting with any guy—with a few exceptions. Here's how to successfully flirt with a guy who's older.
Acknowledge the age gap. Yes, you're younger than him. He knows it, you know it, so if you're feeling self-conscious about it, address it directly. If he likes you he won't mind that you're younger. If he minds then he's not right for you. 25-Year Age Difference: Can It Work?
Don't pretend to know about things you don't know about. Like we just said, he knows you're younger than him—he's not expecting you to remember the '70s, or to have experience raising kids or paying a mortgage. If you feel out of your element, say so. If you don't want to say so, ask him questions. You can't go wrong asking people about themselves.
Ask him for advice. And take the advice seriously. He'll be flattered that you want his guidance, and he has a lot more life experience than you, so he probably knows what he's talking about.
Don't assume that your age makes you more appealing than other women. Yes, youth is attractive, and he may be attracted to your unlined skin and shiny hair but don't get cocky; the older you get the more you realize that you need to connect with a person on a more-than-physical level. If you're looking for a real relationship you need to get to know him and let him know you.
Don't assume he's rich. He probably makes more money than you, but he probably also has more to pay for, especially if he has kids from a previous relationship, or owns a car or a house.
Be yourself. The best advice for flirting with an older man is to be yourself. As you accumulate years you get to know yourself better and get more comfortable in your own skin. He's probably past the insecure game-playing phase that people go through to protect their delicate, young egos. So don't over-think it too much—talk to him like a regular guy, not an Older Man, and you'll be great.