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.

Absolutely not ~ you cannot ask him. If he is or isn't shouldn't make any difference. I don't think it's weird but it is uncommon. Just enjoy the company of a lovely man.

Wasted on her.
You have got to be kidding.

The most obvious and probable answer is, of course, that he's socially awkward and very strange.

The OP should get rid. Pronto.

There may be a sinister reason behind his lack of experience.

At the very best a sexually inexperienced man is no prize.
She's not won the lottery here.

Of course it's a red flag.

I wonder if the people seeing this man's lack of experience as a very good thing would feel the same if the sexes were reversed or would they, as I expect, not be be saying how great it was that this woman was a virgin/lacked experience.

For example, 'if she's a virgin, she's a prize, you can teach her.'

There's never been a time where a man's lack of sexual experience has been prized. Never.

Absolutely!

To me, a player would present a red flag and hints to me that they are unable to form a long term, deep and meaningful/respectful relationship. You can look at these things both ways. You can't judge and have to take each situation at its own merit

My bro was a virgin at 49. Literally never found the right person and is happily married now and very committed/loyal/kind. We think he has (high functioning) Asperger's so that also played a part probably....but Jeez let the guy live and find happiness! Which he has 🙏🏼

It's not a binary choice between player and virgin.
Most men are neither.

Just like most women are neither virgins or promiscuous, nor are most men.

We grasp this concept quite easily when it comes to women.

It's good that your brother has found happiness, and I do appreciate that there may be truth in the adage there's somebody for everyone.
There seems no hints at adhd with this man, though.

At the moment the potential cost of staying with this guy - that he's very weird - far outweighs the cost of ending a 'relationship' that has only had 5 dates.

Not worth the hassle in other words.

Why can't she ask? He doesn't have to answer.

Just take him to bed and find out for yourself.

Not really no, if he’s never met anyone he wants to sleep with then why wouldn’t he. I actually find it reassuring that there’s people out there that don’t just shag for the sake of it.
Whether he is or indeed isn’t a virgin isn’t really your business. I wouldn’t dare ask him this, it’s rude

But don’t you see that it’s that which is unusual. To have reached half a century and never ever met anyone you have ever thought that it might be nice to sleep with them?!

You can’t assume someone is a virgin because they’ve never had a serious relationship. They could have a different girl or bloke every week. Also if they are then that’s up to them it’s their body. In answer to your presumption no it wouldn’t bother me but I’d never know unless they told me because I’d never ask

No

Not really. Perhaps you met someone you'd like to sleep with but the feeling wasn't reciprocated?? Not everyone is confident in that way. Maybe he's painfully shy etc. Its unusual if course but shouldn't be a deal-breaker

So we agree. “Unusual”

Yes I guess we agree 😃
But by the same token I would try not to judge

Where did I say I would “judge”?

I didn't say you did but others posters have.....so speaking generally

I knew of a former work colleague who had always lived at home with his mum, and was her carer after his late thirties. He was shy with all women but had a few male mates who were married with families. He never had a relationship with a woman, probably due to his mother, but he had regular sex with prostitutes. He didn't talk about it, but his mates were less than circumspect . You can't always judge the shy quiet ones by appearences and life experience..

@fivetriangulartrees could be talking about me to be honest - I am indeed a lovely person and three years ago I met a 40 year old man who had never been in a proper relationship and had never had sex. We are very much in love and he is a wonderful, funny and generous man. I am having the best sex of my life with him (I am 43 and have a very adventurous past) and I couldn't ask for more in all areas of our relationship.
My boyfriend had similar reasons around confidence issues and had met a few women in the past but ended up just being friends as they apparently weren't the right choice for a relationship.

I really don't think s*x is sooo complicated that it requires even any previous practice. Find the hole, job done. In 3 or 4 tries it can be mastered. Maybe even nice to enjoy with someone as their first experience, rather than it having lost it's novelty. Women are different anyway, so what worked for a previous partner might not work for you.

And what does "weird" or "unusual" even mean? Aren't we all "weird" or "unusual" in one way or another? Life would be pretty dull if we weren't....

Goodness! You sound lovely!

he's told you he's never had a serious relationship and you're making the giant leap of assuming he's a virgin? and you're going to suggest this via text?

Exactly! No previous experience required really! If you're compatible it'll be fine........!

At the very best a sexually inexperienced man is no prize.
She's not won the lottery here.

He's a person, not an object. 🙄 You sound like one of those frat boys. Are you this revolting in real life? Twat.

Agreed.