Not All Singles Are Swinging

By Cheryl Lavin

December 16, 2018 4 min read

Dear Cheryl: I'm 43 years old and single but far from a "swinging" single. I've barely had any sexual experience at all. I'm so shy I panic when I try to ask a woman out. The older I get, the worse the panic attacks get. I guess they come from having known a few women who seemed to take great delight in turning me down.

My lack of sexual experience is torturing me as I get older. I see so many people around me having fun and doing things without regret or bad consequences, like the married men I work with who flaunt their affairs.

There is one woman I like and want to ask out. The problem is I know she was sexually active, and it bothers me. I didn't think it would, but I keep thinking about her with one guy in particular. This isn't the first time this has happened to me, either. It seems like I always think about the sex lives of women I like, to the point where I'm sometimes convinced I'm psychotic.

I know you must be convinced I'm some crazy, psycho nut job. — Conflicted

Dear Conflicted: I don't think you're a crazy, psycho nut job. But I do think you need professional help for several different issues.

The first issue is your panic attacks. I think the basis of them is that you see women as sex objects, not real people. If you would allow yourself to get to know a woman and see her as a friend — not just someone you want to have sex with — you wouldn't feel as pressured. You wouldn't be asking her for a date; you'd just be asking her to see a movie with you, or have coffee, or watch TV — as a friend.

Once the friendship is established, you could move it to a romantic plane, if that's what you both want.

And the second issue is your unrealistic view of women. If you're 45, I'm assuming the woman you're interested in is at least in her 30s. It would be naive of you to think she hasn't had affairs. Your obsession with her sex life is unhealthy, and it's something you're going to want to discuss with a therapist.

Dear Cheryl: I went out of state for college and wound up staying in that state for 10 years. I recently moved back home. The other day, I was walking down the street and saw an old high school friend. I wasn't really sure it was her at the time — she passed me so quickly — but the more I think about it, the more sure I am that it was her.

I looked her up on Facebook. She's not married, and she works a few blocks from my office. I'd like to call and ask her out, but I don't want to seem like a stalker. — Friendly Guy

Dear Friendly Guy: What have you got to lose?

Call her at work. Tell her you saw her walking down the street and you'd like to take her to lunch. Tell her what you told me, that you recently moved back in town and you'd like to reconnect with your old friends.

I'm guessing she'll be flattered and happy to hear from you. If she isn't, her loss. If you don't do it, you'll regret it.

Got a problem? Send it, along with your tales, questions and rants to [email protected] And check out my e-books, "Dear Cheryl: Advice from Tales from the Front" and "I'll Call You. Not."

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