Look, man, most guys are doing this dating thing all wrong. Someone once told me, if you wanted to sell a book, the hardest place to sell it is a bookstore. Why? Because you are competing with all the other books. I don’t know if that’s true, but it’s definitely true when it comes to dating. If you go to bars, clubs or searching online then you are competing with every other guy there.
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Team play encourages what sociologists call "situational generalization"—in other words, positive circumstances help people click. "When people are working toward a shared outcome, they're more likely to grow closer together," says Parks. Recreational outfits make it easy to form new connections because individuals can sign up and be assigned to a team without needing to know anyone.
Get to know them, learn their names, and remember them! Make it a point to recall what drinks they like to order or foods they like to eat, and of course, flirt a little! Just don't go overboard. A little mystery is fascinating to any mature woman, but especially so for an older one. Flattery is one of your best friends-and believe me-older women will remember it long after they leave. They (or she) will undoubtedly know what you are doing and will love it!
When I worked downtown, I made it a habit to eat at all the local hipster places for lunch. Sure, it wasn’t always cheap however, I noticed an upside to it (aside from the often great food). A lot of women were doing the exact same thing as I was. They’d sit down next to me and we’d strike up a conversation. Yes, women eat alone too! Although, these weren’t always just women that worked nearby. The truth is, a fair number were from out of town, and quite lonely while looking for companionship in the city.
Know when to end the conversation. Going on for too long can make you seem desperate or even scheming. When this woman is someone you'd really like to see again, say something like, "You know, I would love to hear more but I have to get back to work now. Tell me all about it over salsa dancing on Tuesday." Always leave the conversation to be continued. Do not exhaust the conversation as things can turn awkward and she may lose interest.