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

Sorry but, to me, never having had a relationship at 47 is a big red flag. I would also assume any man in that position would either be asexual or a user of paid-for sexual services.

Asexual. Aromantic. Just a hunch. Happy to be wrong OP

The whole concept of virginity is so outdated. If he is a “virgin”, he hasn’t put his penis inside a woman’s vagina. What if he’s done all sorts of other sexual things, just not that one? OP, I would seriously question why it bothers you so much. Perhaps he has, perhaps not. Surely you only need to worry about the time, if it happens, that you have sex with him, rather than worry about whatever time may or may not have happened before.

I am 50. I have never had a long-term relationship, I’ve never found anyone I wanted to share my life with in that way. I have had sex. You don’t need to be in a relationship for that. I have a friend who was in an entirely sexless marriage for over a decade.

Just focus on the relationship as it is now, don’t judge what’s happened in his life before.

Entirely inappropriate

Best advice

Ask him round to get a takeaway and a film. Watch 4 weddings and a funeral. When you get to the bit where Carrie starts counting off all her ex lovers, tell him yours.

I think some of these replies are harsh - my main concern would be that, if he is a virgin, it might be a much bigger deal to him to have sex with OP?

I'm not sure you can directly ask the question though!

Could you perhaps frame it as a question about STD tests or something like that?! (Assuming yours are up to date, it's not unreasonable to ask that question at all!)

Not totally weird no.
There are men who for different reasons haven’t found a woman to be with. Part of the reason could very well be that past a certain age, this very lack in experience is partially what is holding them back.
If we accept that women shouldn’t be asked about their past sex life we shouldn’t be asking men.
I personally wouldn’t be bothered in that there is no correlation between ability to please a specific partner and number of partners someone has had.

It’s in his kiss! 🎤

So if he says that he is, is it over then because you’d think he’s a weirdo? Poor guy.

Dear god, seriously? You’d text to ask if he’s a virgin? While I’m unlikely to ever be on the receiving end of such a text (because I will never, ever date again), my response would probably be a crisp ‘fuck off’.

If you feel you need to know, and I can see why you might, take the approach LavenderDisco suggests.

No I don’t think it would be totally weird at all. Unusual yes. But not weird. Depends why. Unrequited love, shyness, nervousness, chronic fear of rejection, bad experience leading to performance anxiety.

Men can require confidence. The worst thing to do is be shocked. Be kind, understand, pretend etc. if you like him. He might turn out to be wonderful.

You never know, you may lose the love of your life if you text him to ask him if he’s a virgin. I’d run a mile if I were him!

I thought it was only teenagers who cared about who is and who isn't a Virgin.

My last partner had never had a partner and had only had sex once before me (he was in his forties). He was very good in bed 😂

And then I’ve had men with plenty of experience who were crap!

What has happened that he now able to be open about himself when this has been a barrier to any kind of relationship until now?

she can at the right time, but not over a text message as she was suggesting and in a much less intrusive way!!
anyway she thinks it could be weird so sounds pretty judgy so perhaps not the right relationship 🤷‍♀️

You can insist on STI checks without asking about their history.

These two things are completely different.

Yes I think it would be weird to be a virgin at almost 50 and that’s why I think he probably isn’t one

If sex arises then maybe you could talk a little about past history. Otherwise I don’t see what you’re going for here apart from drama

I would just assume he hasn't and take it from there (or not!).

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"

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

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.

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.