Tag Archives: Older Women

“Jaw With John” – Mind The Gap

I am a 54-year-old woman. I have been seeing a 28-year-old man for the past year.

Although I have confided in a couple close girlfriends and he has confided in his two brothers, he has asked me not to disclose this relationship to anyone else. I have respected his request to be on the down low.

I’ve been divorced for over 14 years and have three kids. I had no luck in the dating arena before I met him.

I have no desire for my kids or anyone else to know about this relationship, but I’m wondering: What do you think of a relationship where the age gap is so wide and the woman is older?

I think about it all the time. If same-sex relationships are no longer frowned upon by everyone, why does there still seem to be a problem accepting a relationship like mine?

I wonder what my future is with him, or if we have a future. Am I cheating myself? All I know is that he is brilliant, beautiful, very affectionate and giving emotionally to me. He is just the best overall person I have ever met.

Should I just relax about this relationship or am I just some stupid old lady?

I’d appreciate your comments and advice. — Middle-aged

Dear Middle-Aged:

Watch the movie I Could Never Be Your Woman. It addresses many of your questions, in a cute and hilarious fashion I might add. People never seemed to bat an eye when older men show up with MUCH younger women. I mean, they have, but it is generally more acceptable tolerated more. Just look at Something’s Gotta Give or The First Wives Club: older man with a younger woman. Coincidentally they both starred Diane Keaton but that’s beside the point. Hell, even Anna Nicole Smith did it and people barely flinched (unless they were in that family).

You’re a grown woman and he’s a grown man capable of making his own decisions and he chose you. The obvious question here, if you do decide to keep this relationship going, is what happens when you are 70 and he’s 44 and you’re maybe thinking if slowing things down but he is still active? What happens then? Then, the age difference will catch up.

You also need to address if you want to continue to be his secret lover. At some point his friends/family will find out and so will yours and putting that off for too long could end up to bite you in the ass. Unless you are into that sort of thing…

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“Jaw With John” – Boyfriend Has Lived In Cougar Town

“I found out a while ago that my boyfriend had a “friends with benefits” relationship with someone 16 years older.

The first time I heard about it I ignored him for a day. Didn’t acknowledge him, didn’t talk to him and felt disgusted by him.

I know guys have stupid, weird and crazy fantasies about older women. I finally got over it because I realized how much I love him.

This topic came up again the other day while we were having dinner with one of my friends. I told my boyfriend out loud how disgusting it was. That woman was almost old enough to be his mom! He said he liked it because she had “the body of an 18-year-old.”

Somehow I sense a little pride in what he did and I want to puke. We haven’t talked further about this because I know it will just turn into a bigger fight. Why did he do this? Should I just try never to think of it again? — Disgusted

Dear Disgusted:

As long as he was of age then there is nothing wrong with what he did. I am pretty sure most straight guys have had a cougar fantasy at some point in their life. C’mon, Stifler’s Mom? Those type of women exist. Trust me. Your disgust is a personal preference but if the gender roles were reversed, with a Sugar Daddy perhaps?, would you feel the same?

You sound jealous and bit butthurt. He has moved on from that relationship and has now found something, I would assume, special with you. I suggest you should do the same.

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