To wish I’d slept with more guys?

I get where you’re coming from and don’t think it’s unreasonable unless you’re really dwelling on it. There’s always an alternative life you could’ve lived which could’ve been wonderful or rubbish. I think it’s normal to be curious about paths you didn’t take and it’s easier to ignore the potential downsides as you’ve not had to live through them.

If you’re happy in your life now it’s wasted energy having regrets as it’s your past choices that have brought you to where you are. And that 20 year old could only make decisions with her 20yo experience and perspective. It’s easy to look back with a 40yo brain in a more sex positive 2026 and think you should’ve acted differently.

I agree with this, I was single after a decade long relationship in late 20s and did a few one night stands and casual dating and none of it was very good sex, in my experience men are lazy and selfish in bed with women they aren’t emotionally connected to. You’re just fantasizing.
im 40 now and have been celebate for two years as what’s out there isn’t worth the bother I’m finding!

Maybe. But you can be too married! I know what you mean @britneyisfreebutnotokay . I got married at 23 and there's a bit of me that wonders if the same!

I had a few in my younger years and it wasn't anything special. several mediocre wienerings by rather dull men

ask any prostitute. They will tell you it’s not some wild glorious experience. For most women it’s soul destroying.

👍

Well, it's not what it's cracked up to be, especially in your twenties. However, while I probably (definitely!) wouldn't choose to sleep with most of the men I slept with again, what it did teach me is what I like, what I don't like and how to communicate it to a partner.
Things really picked up when I made a decision to have a number of regular sexual partners with no strings attached. So rather than bringing a random guy home after too many drinks, it would be more like indefinite "early stage dating" - going out for meals, events etc. and then having sex maybe for a few months. Then part ways when one of us found a better offer. Now, that was a lot more fun and a lot safer to boot.
Should you find yourself to be single, I highly recommend this approach.

I didn’t do that though did it. I compared sleeping with lots of men.

I was on the thread and my number is very high. Most of them were shit and I enjoy being with just one person. It’s not all it’s cracked up to be trust me!

Not so much about sex necessarily but I definitely regret not having enjoyed my beauty more and my complete lack of self esteem certainly held me back on many occasions.

Hmmm. You are “nearly 40” so aged 38/39 and you have been with your partner for 20 years so starting from 18/19. So your “prime years” when you had your own flat and wish you’d had random sex were in your teens?

I slept with loads of people, some good, some bad, some OK.

I dont regret it and wouldn't change a thing, I would change some of the people I have had relationships with however.

As for @Daisywhatsyouranswer comparing one night stands or flings to prostitution, thanks, I needed that laugh.

What’s a lot? I’ve slept with 21 men. Mostly while I was looking for ‘the one’, I didn’t enjoy a great deal of them because I knew they weren’t the one and so they were pretty meaningless to me. A few were good fun and as such as nice memories to have which I don’t regret

As someone who slept with her fair share of men in her youth and tbh I probably had your share too... you really arent missing that much.

Would you really have enjoyed it. Sleeping with random men. Them leaving, many not wishing to see you again, treating you like a body. Nothing more.

ask any prostitute. They will tell you it’s not some wild glorious experience. For most women it’s soul destroying.

Massively overrated

I’ve definitely had my fair share of fun.

I remember feeling ashamed for how much fun I had in my late teens, early 20s and so I went celibate for a few years.

But now I wish I had more fun as it doesn’t feel the same doing it in my mid 30s.

So basically I can’t win and other people probably feel the same.

Some men are absolutely shit in bed though and so if you have good sex with your DH then you haven’t missed out on anything.

I am very monogamous and love the sex I have with my DH but think there’s some truth in what you are saying.

If I became single then who knows?!

I am thinking of the older female character on ‘Benidorm’…😁

As someone who woke up in the morning to one too many strange men, YABU. I don't miss those awkward mornings. 😂

@britneyisfreebutnotokay I felt this way in my 20s. DP was my first and only. We met at 18 and somehow stayed together through long distances and many challenges. I was really attracted to lots of men in my younger days and often pined for them, but somehow I knew that DP was still the one and I should never take him for granted. My love for him was stronger than my lust for variety. I never strayed and I didn’t give in to the temptation of finishing with him so I could have some more different experiences. Believe me, I was very tempted.
Now in my fifties, I’m having the best sex of my life, with a man who knows me utterly and loves me completely. I want to go back to my 25 year old self and thank her for the gift she gave me. He’s the best.
That said—if you feel exploring more is right for you, then do it! You only get one life. Live it.

But is she? Maybe we read it differently. I read "I wish I'd done that then" not "I want to uproot my life now". No matter. Take care.

Yes exactly.

That's why OP wishing she had had lots of casual sex in the past is pointless.

But she has the capacity to change her life now and have casual.sex now if that's what she feel really is right for her.

Before I separated from my ex I’d only slept with 2 people. Then we split and I started going to swingers clubs, I’m having so much fun and loving sex again. My motto is you only live once so have all the fun you want with no regrets.

Haha I think that too sometimes...so many wasted opportunities I just didn't realise at the time.

Of course. But you could feel like that about loads of things. If you contemplated every decision retrospectively then you would go crazy.