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.

Of course you can’t ask him. You have no right to know. Would you be happy if he questioned you about your sexual history?

Does it really matter if he's a virgin?

I hope you give him a chance if he’s lovely.
Have another date and probe more if you need to, but don’t write him off immediately. You might be making a big mistake.

You can strike up a general conversation in the hope that he will share the information, but I dont think asking outright would be the right thing to do.

If i was on a date and the person asked how many people I had slept with I would run a mile.

Would it change whether you wanted to see him again if he hadn't had sex? If so its maybe better to end it just now.

Do none of you think that would be totally weird to be a virgin at almost 50?!

How do you take a leap from not having a serious relationhship to be a virgin
either way you cannot and shouldn’t ask him about his sexual history

He's highly likely a virgin but you can't ask him. If I was dating a virgin, I think it would be nice to be his first, quite exciting! Just find out as you go along!!

I was going to ask in a message not face to face and say of course he doesn’t have to share if he doesn’t want to

Be bloody careful beforenyou fall in love with someone who's never had a long term relationship. Most people make their teenage relationship fuck ups when they're, you know, a teenager. It's much worse being on the receiving end of those fuck ups as an adult, with work and kids and god knows what other responsibilities, especially if your lives have merged at all.

Don't do it to yourself.

Let him go, go be judgement on your own.
Poor bloke

unusual - yes

Very, but there are plenty out there! Better to have not made lots of mistakes than be a player!

Noooooooooo!

It doesn't matter what we think, we are not dating him. It only matters what you think. What is your concern if he is a virgin? If you can identify what you are worried about it will help you decide next steps more clearly.

This would be so demeaning and intrusive of you
I don’t think you and he are well suited on any level

Just because he hasn't had a serious relationship, doesn't mean he's never had sex. I'd be more concerned about those insecurities and whether he's done anything to overcome them.

Uncommon, yes, these days, but not totally weird.

Yes I would definitely find it weird but not necessarily a dealbreaker! It’s something I’d rather know about though before ‘going in’, as it were. So I don’t agree that you can’t ask him - I think it’s about how it’s pitched / phrased. You could gently
explore topics like intimacy as part of chats about relationship experience, and he’s already opened up the conversation about his relationship history.

Edited to add - do NOT do this over text!!!

God dont do this!!

So you're actively looking for something to find weird about him?

Either have sex with him or don't but I can't see why it would matter whether he's done it before.

It happens. If you're attracted to him and like him, you could have some more dates and see what develops.

Clearly it would be relatively unusual, but I suspect it may be more common than many people realise, as it's not the sort of thing people are going to broadcast.

Wtf?

Op can and should ask him about his sexual history - we're not in the 50s or before when sex was a matter for secrecy and embarrassment. If you are thinking this relationship has legs I'd ABSOLUTELY ask him about his sexual history - this age group is historically most likely to contract STDs because we assume all is ok 'at this age' or are still too prudish to ask about STI checks and partner's history.

No. Sex just isn't that important for lots of people.

Yes you can absolutely ask him this. He's opened the door to the conversation by sharing what he has. If he isn't a virgin, he may well be lacking in experience. If either of those two things are the case he's probably quite nervous and self conscious about sex and being able to talk openly and without embarrassment from either of you would certainly help you have a relationship.

Be straightforward and kind and curious
"So the other night you mentioned that you hadn't had a longterm relationship. Would it be OK if we talked a bit more about that?... I wondered about how experienced you might be and if you were comfortable talking to me about that and how you'd like to move forward with me"