15 Women Reveal Their Biggest Sexual Regrets

woman in bed

Sometimes it is the wrong guy, or the wrong place or just plain awkward, but sex regrets happen to the best of us. Read on to hear the biggest regrets from real women. 


While I’m not sure there is a perfect place to lose one’s virginity, I can say with certainty that the back seat of a borrowed Volvo station wagon is NOT an ideal location. Really, the only good thing I can say about it is that, because it involved another rather inexperienced person, it was over rather, um, quickly. We've collected some other stories that don't involve station wagons but still come with the same dose of regret.

Good luck reading #5 without getting a headache.

1. “My biggest regret is the sex I didn’t have. He was a gorgeous Irish exchange student (that accent still turns me on) and I was too naïve to realize that he was hitting on me the last night before he left to go back home.” -- Cari R.

2. “I did *something* with my now husband, when we first met. I did it again a few times over those first years, always when drunk. He thought I liked it. I soooooo don’t like it. I regret letting him think it was something I like and was willing to do often.” -- Shannon H.

3. “Occasionally curiosity makes me wonder if I would have enjoyed being a little more ‘active’ before settling down. But I’m happy with what I chose.” -- Autumn C.

4. “This may sound super prudish or something, but I was my husband's first and only girlfriend, so I felt really guilty and awful that I'd done anything before I met him. These were all things that I already felt guilty about, so knowing that he HADN'T made those same mistakes made it harder. It was super special and amazing every time we did something new, knowing that he'd never experienced those things before.” -- Jessa M.

5. “My college boyfriend and I were having sex in his bunk bed. I was on top and flung my head back in passion and slammed my head into the top bunk and knocked myself out. Waking up naked with a freaked out RA calling campus police is one of the low moments of my sex life.” -- Cameron V.

6. “I may regret them, but I promise they don't regret me! I will say as women we shouldn't be so hard on ourselves and act like our past is a patch of shame. My guess is most men would answer this question with, ‘My only regret is that I didn't bang the girl next door'.” - - Bethany P.

7. “I kind of regret never doing anything with a woman. I'm into men, but still, just curious sometimes.” -- Lisa V.

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8.Nope. I made a lot of bad choices in my teens and 20s but I wouldn’t be who I am without those experiences. If anything, I'm grateful that it all worked out and I'm married to an amazing guy. It could have been much, much different.” -- Helena R.

9. “Right up till I met my husband. I wish I had respected myself and my body. I wish that I hadn't allowed myself to only feel worth something when a man found me attractive. It took me a long time to forgive myself, but I finally have and know that it has made me who I am today. I just hope that through my mistakes, I can teach my daughter self-respect and how to treat her body like a temple.” -- Fiona H.

10. “Only a few I didn't do. ... okay, maybe a few I did do too …” -- Leigh P.

11. “I have one big one and one little one. Both involve drinking too much.” -- Annie T.

12. “I wish I hadn’t wait until I was married. It turns out my ex and I were really not sexually compatible and it was one of the reasons we broke up. I’m married again and this time I definitely sampled the merchandise before I committed.” -- Colleen D.

13. “I let an ex-boyfriend talk me into some kinky stuff like golden showers and spanking. It wasn’t a turn on to me and I wish I had respected my own boundaries more.” -- Elizabeth J.

14. “When I was 15, I told my male best friend that I thought I was a lesbian. He spent the next six months trying to convince me that I couldn’t know for sure unless I had sex with a dude. I eventually gave in and had sex with him. And, yep, I am definitely a lesbian.” -- Drea G.

15. “I let a boyfriend take naked pictures of me and then we broke up. He swears they are deleted but I’ll be nervous the rest of my life that those photos are going end up online someday.” -- Rachael O.

What is your biggest sexual regret?

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