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

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.

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.

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 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 😂

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.

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

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

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

You’ll be the best he ever had!

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'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.

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.

Double noooooooooooooooooo

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?

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.

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?

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.

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.

Did he live with parents for a long time?

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.

WTAF. Maybe he can ask how many guys you've given a blow job to, perhaps by text too

I think you can ask him.

But not until the relationship has progressed a fair bit further ie until it looks likely you might have sex.

And definitely not by text!

It’s unusual, but not necessarily a red flag. If he’s been overweight all his adult life then it’s perfectly possible he’s lacked self-confidence and been too shy to approach women and initiate a relationship. I wouldn’t write him off based on this alone, OP, when it sounds like you really like him otherwise.

Why is it so important to you? Even if he is a virgin, you would both be new to each other. It could even be an advantage in that he wouldn't be expecting you to like the things previous partners had liked and he'd be keen to learn!