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How To Date An Older Woman

We asked several women who’ve dated younger guys to tell us how to do it. And if you refer to them as “cougars,” you’re already doing it wrong.

By JL Scott

Tips For Dating Older Women

8. NEVER GUESS HER AGE
“I once dated a guy who realized I was older and he started guessing my age. He started with 35. Next!” —Erin

9. DON’T ACT YOUR AGE, PT. I
“Hey, I love laser tag and beer pong, but I want to be the one to suggest those activities. I’d rather a younger guy suggest something like going to a new restaurant or bringing over a bottle of wine to my place. It makes me feel like I’m a girlfriend, not a babysitter.” —Ainsley

10. DON’T ACT YOUR AGE, PT. II
“I was meeting a younger guy for a first date. Dude was 20 minutes late, and when it came time to pay, he hit up the ATM machine in the bar. Later, he explained that he had no money because he’d spent it all at the bar the night before.” —Wendy

11. DON’T ACT YOUR AGE, PT. IIII
“I thought everything was going well with this one guy … until I went back to his place. All of his clothes were on the floor. And I mean all his clothes. He didn’t have a dresser because, in his words, he didn’t know how to buy one.” —Elizabeth

12. SHOW HER OFF
“I really liked when a younger guy I was dating asked me to his buddy’s BBQ. I knew most of the guys would be a lot younger than me, but I was happy he wanted to let me into his life without it being a big deal.” —Teddy

13. BE MATURE, NOT STUBBORN, ABOUT MONEY
“I once dated a guy who was still in school while I had a job, and he still insisted on paying for everything. Once we were at a restaurant and he must have misjudged the prices because he started pulling a bunch of quarters from his wallet. He even pulled out a five pound note from England (we were in America) from his wallet and wondered if they’d take it rather than just let me pick it up.” —Annabelle

TAGS: dating older women, how to date older women, sex

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