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dating coach for smart, strong, successful women Evan Marc Katz
I’ve been spending a lot of time with an attractive, interesting man these past few months (I’m 37, he’s 32). Until recently, we were just friends – dinners, cultural events, hikes, lots of long intellectual conversations and escalating sexual tension. While we were having wine at my house last week, he finally made a pass at me and we ended up sleeping together.

This was a big deal for me; I had been celibate for 3 years. In fact, I’m extremely sexually conservative – I only lost my virginity when I was 27 and in the seven years since breaking up with my ex, I’ve only had sex twice, including sleeping with my friend. I had been hoping he would make a pass at me so I was glad when he finally did, but I deeply regret having slept with him. I knew I would regret it but I pushed myself to do it because it had been three years and – goaded by my therapist – I was trying to work past my sexual hang-ups. Also, I like him. But I should have been true to my sexually neurotic self; it was too soon for me, and it was especially too soon considering that we’re not even committed to each other.

Since we slept together, he has shown no signs of losing interest in me; if anything, I’ve heard from him more often and our fun, playful, cerebral dynamic hasn’t changed. He was very affectionate and attentive to my needs during our night together. I don’t want to stop spending time with him and I’d like to keep exploring what’s developing between us, but I don’t want to sleep with him again… at least not until I figure out how I really feel about him. How can I take that step backwards… CAN I even take that step backwards? I’m afraid of offending him, and I feel guilty about changing the “rules”. Any advice would be greatly appreciated!

Julia

Most people who ask for advice aren’t really asking for advice; they’re asking for validation.

A shorter version of your question might read:

Most people who ask for advice aren’t really asking for advice; they’re asking for validation.

“I want to stop sleeping with the guy I’m sleeping with. Please give me your expert opinion and tell me you agree with me.”

The only good (read: satisfying) advice would be: “Yes, I agree with you.”

Unfortunately, that would be a really boring advice column.

Whatever the original poster asks, I’d agree, she’d feel better, and nobody would learn a thing.

That’s why I pretty much NEVER choose a question where I agree with the original poster.

It’s not educational. It’s not entertaining. It’s essentially worthless.

What I sacrifice in agreeableness, I make up for in valuable and sometimes controversial content.

Years ago, I had a woman write to me about not sleeping with her boyfriend because she wanted to get closer to God. I told her how I felt. Christian virgins have been excoriating me ever since.

Which brings me to your question, Julia.

My advice is never about “right and wrong” but “effective or ineffective.”

My advice is never about “right and wrong” but “effective or ineffective.

Does your behavior get you what you want or does it sabotage what you want?

In my opinion, sleeping with a guy and then claiming “I don’t do that” sabotages things.

It paints a picture of you as confused, fickle, and insecure.

It suggests that you may not have a healthy view of sexuality.

It may hint that you’re having second thoughts about him or that he’s not attractive to you.

What it does not do is make him feel encouraged or strengthen your relationship.

By the way, that’s okay!

You don’t OWE sex to a guy because you slept with him once.

You’re not OBLIGED to do something that makes you feel uncomfortable.

You can ABSOLUTELY tell him exactly what you told me:

“I’m sexually neurotic. I made a mistake. It was too soon. I’d like to take a step backwards and explore a friendship first before we have sex again.”

If that’s how you feel, by all means, go ahead.

Hey, for all I know, he’ll be perfectly fine with going backwards. There are exceptions to every rule. Still, my job is to give the rules:

If you’ve slept with a guy once, it feels pretty insulting if you don’t want to do it again — no matter how you frame it.

Your choice — and it is YOUR choice — to start over is well within your rights, just as it’s well within his rights to determine he wants a woman who doesn’t make such a big deal about sex.

Whatever you choose, I hope it works out for you.

Please come back and tell us what transpired.