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Women Confess Their Greatest Sex Regrets

These bold and brave admissions may surprise you.

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Thoughtful woman looking away while sitting on bed at home
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My boyfriend recently opened up to me about a particular sexual fantasy — something he wanted to make a reality with my help. The details of said fantasy were slightly outside of my comfort zone. At the same time, however, the idea completely turned me on. I was equal parts hesitant and eager: Could I? Would I? Should I? I wasn’t prepared to offer him a yes or a no, and so I said … “not right now.” But I was definitely thinking, Maybe in the future.

Midlife has me keenly aware of the undebatable fact that time passes too quickly. While I sure hope to be alive and healthy(ish) for at least 40 more years, I know that my sex drive will likely die much sooner. That has me wondering: Should I be indulging in my every fantasy while my mind and body are sexually in sync and up for the challenge?

Behind my reluctance to try new things in the bedroom lies the fear of regret. What if I do it and feel dirty afterward? What if I do it and spend the next weeks and months wishing it never happened? Or, on the other hand, what if I never do it and in five years I am postmenopausal, with an extinct libido and no more time or desire to spice it up with the man I love? Will I regret not taking more risks in the bedroom?

In an effort to learn from women who have pondered such very questions, I reached out to girlfriends near and far and asked: What are your greatest sexual regrets? The bold and the brave answered honestly. Some wished that they had done more.


“I wish I had found someone experienced that I could talk to rather than trying to discover everything out on my own (secretly). I would extend my focus from simply the nuts and bolts of how sex works to the emotional implications, how to know when you are ready, how to choose a partner, danger signs, etc.” — Amy, 42, Maine

Taking risks

“I wish I had been more open to trying new things. I wish I hadn’t been so afraid of being judged. And most of all, I wish I had been more confident in my own skin. Because at the end of the day, our sexuality is one of the most important parts of who we are. And it should be celebrated, not hidden away out of fear or shame.” — Sofia, 57, Oregon

Embracing kinks

“It wasn’t until the last few years that I was able to open up about some of my kinks. For the longest time, I have been in love with feet! Don’t ask why, there is something about them that turns me on. However, this was something that I shared only with long-term partners that I trusted. Often, I felt a sense of shame, concerned that other people would judge me. It wasn’t until I reached my late 30s that I said ‘screw it.’ I am now 42 and have only grown more confident in myself. Embracing sexuality includes any weird kinks you might have! My only regret is I didn’t do it earlier.” — Amber, 42, Australia

And others wished they had done a little less.  

Sleeping around

“I regret [what I refer to as] my ‘free-love’ phase. It was after my divorce, and I was celebrating a new, sexual freedom. I went a little crazy and had a lot of casual sex with men I met online. Now that I am in a serious relationship with the true love of my life, I feel ashamed of my behavior. I should have waited for the right man out of respect for me and for him.” — Lisa, 48, New Jersey


“When I first started having sex I was in college, and I couldn’t do it sober. It felt so awkward and was not at all enjoyable. When I was drunk, I played the role of who/what I thought my partner wanted. It was an act, but I was good at it. I pretended to enjoy it. I said and did the right things. I felt brave and sexy when I was drunk. I thought sex was just about pleasing a man and so that is what I tried to do.” — Jami, 38, New York

Hitting send

“Hands down my biggest regret is sending inappropriate photos. I sent photos to several men in the past and I cannot stomach the thought of it today. It felt harmless at the time and I only sent them to men I ‘trusted.’ Ten years later and I am still wondering if New Jersey Mike deleted my late-night photos.” — Caryn, 42, Massachusetts

We all have a regret or two, girlfriends, but let’s not get too stuck in the past. Be gentle with yourselves (past, present and future) and learn from your mistakes. And if you, like me, are feeling rushed to have as much mind-blowing sex as you can before it’s too late … well, stop right there. Sex therapist Zoë Ligon, owner of Spectrum Boutique, calmed my hormones with this tidbit of wisdom: “Great sex doesn’t end at a certain age, stage, or after menopause. There can be multiple primes in your life where you’re having ‘the best sex of your life’ — because a sexual prime is largely a made-up concept. Great sex comes from our mental attitude more than anything else!”