I presume this would bother you too… how can I phrase this to know one way or another? Can I even ask this?

[Howyoop]

Met someone five times now. Really get on well, message a lot in between, lots in common. He’s around 10 years older, I’m 39 he’s 47.

He hasn’t had a serious relationship before. He told me this last night on our fifth date. I asked a little about it, he said he was painfully shy and has had insecurities which he thinks didn’t help. His three other siblings all been happily married for a long time with children.

He said he had liked a lot of people and there had been ‘brief things’ that hadn’t materialised as he hadn’t met the right person. I didn’t go into it more than that but now I am actually wondering if he’s never had sex before?

I don’t think I am being shallow wanting to know this. I am not sure how I would feel if it turns out he’s a virgin. I want to know before I see him again. How do I ask this? Can I even ask this? He’s been completely lovely and I don’t want to upset him or make him feel uncomfortable.

I would just see how it goes when things progress sexually. You will know pretty quickly if you gel or not. Same for the relationship generally, if he's not had any / many - you can see for yourself. I'm sure the conversation will turn to the past and you will find out more, ask questions etc.

Did he live with parents for a long time?

I wouldn’t be keen, but if I liked this man, I wouldn’t be contemplating asking him by text! I think that would be brutally insensitive, reductive and plain rude. By all means have an actual conversation. And if you think that is too awkward, then that probably indicates a lack of investment in the relationship.

This would totally give me the ick. Having not had a relationship is odd but not having had sex by that age just seems weird.

Ffs do NOT do this!

And, yes, I do think it's weird not to have had sex at 50.
But you don't know that's the case, do you?

OP you have to be GENTLE here. If you're right then he's potentially very vulnerable to being hurt.

The real question is, do you like him?, do you fancy him? do you want to explore the possibilities of a relationship?

I think this is a good point. First sexual relationships (or good ones you actually enjoy and learn things) can be very emotionally intense at any age. When you are both relatively inexperienced it's fine as you grow together or if you are young and inexperienced and get a more experienced partner it's a learning thing that's shared. But if one of you experiences all this emotion for the first time at nearly 50 and the other has already done it and is a grown mature adult, I imagine it might be as above. Maybe not as bad, but certainly elements of it.

Been messaging more. He’s clearly not keen on going into detail much but then again I’ve barely asked anything further based on all the advice here!

I think I do really like him and that’s what’s making me a bit anxious. I’ve had some absolutely terrible experiences with men and I just don’t know if I can take another one. I suspect I may be looking for problems as a defense mechanism.

Turn the tables - if you were feeling stressed and inadequate about your own lack of experience (if, indeed, he is) would it help for your new partner to quiz you about it? Or would you prefer just to try it and see how you got on?

Double noooooooooooooooooo

I tend to assume that sexual inexperience is more common that most people think. You really don't know how much sex other people have actually had.

This probably applies to most people you've had sex with, too. I've never been in the habit of discussing my partners' sexual history so it's possible I've slept with a lot more virgins than I know.

That said I wouldn't assume that inexperience in relationships means anyone's a virgin. I didn't have a real relationship for around a decade after I started sleeping with people.

And no, you can't ask him outright unless the conversation directly leads you there. Talk around it. You can talk about sexuality and experience as abstract concepts so you're both saying what you feel but it doesn't seem quite so personal. Use popular culture for examples. You can talk about virginity as a concept without talking specifically about his maybe-virginity.

But all that said I don't think it would bother me. There are risks that it might not be a great experience but that's true of everything and you can cross those bridges when you come to them.

You're definitely not going to get that with someone with little to no sexual experience! I love sex, and have had good to great sex since I was a teenager. But the mind-blowing sex came as a combination of me getting more experience as a got older (as in, my 20s, but I did have A LOT of sex by that point 😂) and being with other people who also had a lot of experience.

I'm not saying that'll be the same for everyone, and it doesn't have to be a lot of sex with a lot of different people - when you're in a long term relationship with great communication, the sex is bound to become mind-blowing.

Yes. Surely being shy can’t be the only reason he hasn’t had a relationship by his age! That in itself is a red flag to me.

You’ll be the best he ever had!

There's a substantial minority of men who have had very few or no relationships, so this is not particularly unusual.

This is different. It is important to know beforehand in case there is anything you can do to make things easier for them.

Bloody hell OP, you are seriously overthinking this. Just take it one date at a time and see how things go.

Ah you know what, he actually sounds really lovely and the fact he’s recently lost 7 stone likely means he is feeling more confident and secure in himself. There are so many awful men out there, how sad it would be to chuck a potential gem away due to fact he’s not had a serious relationship before. I’d say give it a few more weeks before you decide and see how things evolve.

I think if you ask nicely then you can, but it may make him feel uncomfortable.

I think if you are going to start a sexual relationship then you should be able to ask about sexual history, I don’t understand the fuss. I see it from a what kind of things have you enjoyed before and also a sexual health point of view.

I have had conversations like this in the past, and it’s never caused upset, quite the opposite.

Maybe I am still a bit 2000’s though 😂

If he's been overweight most of his adult life and is shy or self-conscious as a result, it would be less surprising if he's 'inexperienced', and that doesn't mean there's anything wrong with him as a person. No, I wouldn't ask such a personal question so early in a relationship.

There are no guarantees in life or love. If you like him and get a good vibe from him, all you can do is take things slowly and trust your instincts. That's all anyone can do. But if the thought of an inexperienced man is off-putting, you can end it now. It's your choice.

I would want to know but wouldn’t ask. I guess I would try to create a situation where he would feel comfortable enough to tell me and talk to me about it.

Or if he was up for it, I would just shag him and resolve the question.

Unusual, but doesn't mean there is something "wrong" with him - my grandfather was 40 when he married my grandmother (who was 22) and had never been with a woman before. They had a blissfully happy marriage which produced 8 kids. Some men - particularly very sensitive, introspective ones - are late bloomers, and I think if you get to 40 without having sex it's very easy to then get to nearly 50 as women get put off if they find out, his confidence dwindles, he becomes risk-averse, and the problem becomes self-perpetuating. This quality runs in some of the males in my family, including another close family member, who is an absolutely lovely person but has never had a relationship for these reasons.

If your attraction to him is based on whether or not he's has sex before then maybe it's not genuine attraction. But if you do like him and you are really attracted to him, then give him a chance.

No.

It’s uncommon. But not impossible.

I would suspect he has severe confidence issues, or neurodivergence and perhaps mental health problems because of this.

That being said, you don’t need a reason to not pursue anything further with him. If you’re not feeling it. End it. For his sake.

Some people would say you've no right to know, others would say that if you're sleeping with someone, you do have the right to know their history. For example, if 2 people were both virgins but the woman was post menopause, they might decide not to use any protection, if neither partner had had sex for decades, this again might affect things in terms of STIs (before anyone snaps it's still not 100% safe, ok, but most people would think the risk levels are very different if Mark was sleeping with 10 people on an average week, or if he'd only had sex with his virgin teenage girlfriend decades ago).
And if someone was a virgin, or didn't believe in sex outside a serious relationship,you might want to do things differently, or take a bit longer before deciding, because it could mean that person has a totally different set of beliefs to you.

Do you not think that if he is inexperienced he is likely to be a little nervous and you drawing attention will put additional pressure on him that wouldn’t be there if things happened organically ?

I dont think hes a virgin he could have a serious kink that women dont like,.if it were me id want to know why his relationships ended and does he want a serious relationship...does he have a mortgage and a good job or is he living with mummy...if hes never had a relationship that doesnt bode well