Ask Ava

Ask Ava: Dating Older Women for the First Time

Couple on Date

Q: Dear Ava. I’m a first-time cub. What I mean is, I’ve decided to widen my dating-age group by messaging older women I see on dating sites. This came about because most of the girls at my college bore the crap out of me. I don’t want to stereotype but it’s all clothes, makeup, celebrity gossip, and reality tv. A lot of my guy friends are into this stuff too, but I don’t want a relationship with them! Before I met Carrie the Cougar, I was scared to death. I even thought about lying about my age because I didn’t know if she’d want to date someone so much younger (eleven years!), but she assured me that age has never been a factor for her. We’ve seen each other a few times, and it’s going well, but I want to sweep her off her feet, impress her, and maybe get serious. How does a young guy romance an older woman without coming across as a doofus? -Dale

A: Hi Dale. Yay for first-time cubs! I’m always happy to welcome new cubs into the cougar dating jungle. I don’t want to generalize either but men my age are always talking about work, money, and their ex-wives! Dating outside one’s box (whatever that might be) can be a little scary at first, but remember, reward often comes with a little risk which in this case is the unknown.

Carrie is right. Older women – younger men relationships are so commonplace now that eleven years isn’t by any means the biggest age gap. If you feel hung up on the age difference then others around you (including your lady) will also take issue. Be confident in your relationship and never bring up age with a cougar.

We are not a separate breed (despite our moniker), so what impresses most women will also impress a mature woman. Honesty is number one and that includes being yourself; you don’t need to try and act more sophisticated than you are or pretend to be into what she’s into. Share and explore what makes you different. Engage in conversation that will help you get to know her better – questions, questions, questions. And really listen.

An older woman has seen most dating games that people play, so don’t bother. You like her – ask her out. You want to know how she feels – ask her. The chemistry isn’t right – move on. This no-nonsense approach is highly respected by cougars.

All the Best, Dale, in your new adventures with older women?

Cougars: What can a younger man do to catch your attention?

Need advice on dating, relationships, or sex? SUBMIT YOUR QUESTION HERE, and who knows, you may appear in the next Cougar World newsletter. -xo Ava

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