Have you ever had sex and instantly regretted it?

Jack’s Answer:

When I was twenty-two, I got a page (remember pagers?) from an ex who was back in town after moving away shortly after our breakup.  She was the last person I wanted to hear from; fortunately there is nothing less confrontational than a pager.  The other party can’t have any direct contact with you unless you call them back.  Of course, I was horny and, knowing that you can’t spell “sex” without “ex”, I gave her a call.  We went out that night, and given that she was at best clingy and at worst emotionally unstable, I was extremely cautious.  We made small talk during drinks and dinner: How’ve you been, how are your parents, have you seen such and such movie yet, etc.  There was no discussion of resuming our relationship.  We didn’t even bring up sex.

After dinner, we returned to my place, where sex did in fact occur.  Overall, the experience was enjoyable, providing both an exciting spark and a more comfortable familiarity.  Although our dating relationship left much to be desired, physically I had always been in-tune with her.  Now, some eighteen months or so after the dissolution of our relationship, there were no emotions or egos to get in the way of what I hoped at the time was simple no-strings-attached sex.

When we were finished, we dozed off and I remember waking to the very unsettling thought of her wanting to begin our relationship anew.  It made sense; as stated above, she was a very clingy and emotionally insecure person.  I, on the other hand, was over her, and the last thing I wanted was to actually date her again.  With my climax not far behind me, I had a moment of clarity.  I realized the risk I took, and in fact did briefly regret hooking up with her.  At any rate, my fears were unwarranted.  When I dropped her back off at her parents’ house where she was staying, it became clear that she was no more interested in dating than I was.

Jill’s Answer:

No, I don’t believe that I’ve ever regretted any of the sex I’ve ever had, either instantly or days, months, or years later.  Whenever I’ve had sex, I’ve always made the conscious decision to do so beforehand, and I generally knew what I was getting into, including any likely risks.  Therefore I didn’t regret it.  It was simply what I wanted at the time.

When I was single I had a few one-night stands.  I usually enjoyed the sex, I knew I only wanted the quick, meaningless release, and I got what I wanted from the situation.  I always knew that it was only a one-night stand, I didn’t feel bad that it wasn’t more than that, and I never felt that I was used or somehow taken advantage of by the guy.  I’m a strong believer in my own sexual agency.  I like to take charge rather than letting things happen and going along for the ride.  If I was ever in a situation where I knew it wasn’t a good idea to have sex for whatever reason, I made the conscious decision not to.

The closest I’ve ever come to regretting having sex was with the guy who assfucked me without asking, warning me, or even lubing up.  It was physically painful, and shocking because up until that point he was someone I enjoyed being with, and the sex was really good.  It was unfortunate that he chose to do something so inconsiderate, but I don’t even regret that, as it showed that he was clearly unworthy of me.

Although there have been relationships that I chose to stay in longer than I should have, I don’t regret the sex any more than I regret the relationship itself.  These situations demonstrated to me what I wanted and didn’t want out of the next one.  Therefore I feel that each experience I’ve had, whether sexual, romantic, or otherwise, led me to have the strong commitment that I share with Jack.

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