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.

Has anyone been with a man who is older and not had sex? I don’t know why I feel strange about it. I suppose just wary of another let down relationship

@LadyValerie well I hadn’t even considered that!

Very very unusual, but if he is decent, give him a chance. In our depraved world we seem to be OK with people having sex from age of (don't even want to write it, it is awful) and girls get pregnant at 12? So naturally we think that he must be a weirdo, which is not necessarily the case.
You are absolutely right to ask him, if you want, if he had sexual experience if you want to continue with him.

My sister when out with a powerful American movie executive, she was 24 he was 36 and he had not had sex before - he was a practicing Christian and wanted to do everything accordingly. They split up and he only married and had his first child when he was 50. I don't know if he had sex after 36, but before - definitely not. Very unusual, but not unheard of. He had money, looks, thoroughly decent chap. So not all of them over there in the film business are like that sordid guy.

Don't ask cold, certainly not over text! Maybe you will get there as part of a conversation but you don't want to scare him off!

(I have a male friend who would 100% fit the bill of the person you described other than they have 2 siblings not 3. He is lovely and it upsets me he hasn't found the right person yet)

@indigorising he recently lost 7 stone

Certainly better a virgin to porn addict or a frequenter of prostitutes.
Less chance of HIV/HPV/HSV and a multitude of other STI’s.
Maybe when you discuss exclusivity and sexual health/pregnancy prevention etc you can find out more.

Would it make you happier/more relaxed if you discovered that he'd had sex (however rarely or frequently) outside of the context of what he'd consider a "relationship"? I'd certainly rather he'd never had it than that he'd paid for it, just for example. But if your hunch is right and no relationships means no sex, then he's inexperienced whether or not he's technically a "virgin". That may be a big drawback for you, but there are other challenges as well - the lack of any relationship may mean he has a lot to learn about communication and compromise in the context of a pair-bond relationship but most importantly, if he's STILL painfully shy that is likely to have a big impact on the relationship.

If the sex question is really critical you COULD just ask, or you could hint around, or you could "overshare" yourself, or you could try to couch it as a joke and see if that starts a serious conversation - but prepare for any one of these to put him off if it feels too soon/crass to him.

Where did you meet him OP. I probably missed the post. Has he said he's looking for a full on relationship or is he looking for companionship. Surely that's the first question to ask.

That’ll have made a huge difference- go slow op.

I would be vary wary about entering into a relationship with someone aged 50 who has never had any sort of serious relationship. I would also be wary of his self confessed "insecurities". Tread carefully OP.

@Slugfest i thought it was nice he shared that tbh

What makes you equate serious relationships and sex? I didn't get into a serious relationship until I was in my mid twenties but I had a lot of sex before that. The "brief things" that didn't materialise could have been sexual and never progressed. But no I don't think you can ask if he is a virgin, as others have said, how would you feel if he started questioning your sexual past.

Have you had a snog yet ? If so, did it all seem nice and natural? Do you want it to become sexual ? Xx

A good friend of mine never had a relationship until he was 40, had no interest in sex outside a loving relationship, but then met someone lovely and has been in a perfectly 'normal' relationship ever since.

Someone above mentioned wanting to confine teenage mistakes to your teens - well, he was a bit like a teenager when he first met his partner, in that he was giddy with excitement and happiness, but he wasn't a teenager, he was a proper grown-up who knew how to behave himself and be an adult.

Anyway. I suppose what I'm saying is that he was a virgin until 40 but no red flags to be seen.

You can definitely ask him if he's a virgin and it would have flowed naturally from your recent conversation. Since you didn't ask then, it would be really inappropriate to ask him via a message. Bring it up next time you see him, but do it gently.

What....being shy, does not make someone defective! Being scared to show their true selves for fear of being found lacking says more about the people in their lives than them. Everyone deserves a chance until they do something to deserve otherwise.

See to me the fact that he told you he hadn't had a LTR and that he has insecurities (which are understandable if he was previously unhappy with his weight, amongst whatever else has been going on in his past) indicates that he wants to have a relationship with you, but is scared. He wants you to enter into a conversation about his past. He wants you to help him say whatever he feels he needs to tell you.

He didn't have to tell you he's never had a relationship. But he did. He chose to for a reason

Yes though, I would be wary about it all. It is unusual. He might be lovely. Or he might be very odd. Take it slow

Two things jump out

One I think people saying you can't ask him are being weird. If you're going to embark on an intimate relationship with someone of course you at some point have to talk about sex. I wouldn't ask him in a way which is prying or suggests you find it weird and I definitely wouldn't ask him via messaging/text. But you can't avoid that topic altogether.

Two, I would be a bit careful. It's not necessarily a disaster that he's never had sex but if he has hangups about sex you could be setting yourself up for a world of pain. I had a relationship many years ago with a guy with major sex hang-ups and honestly after a while it did a real number on my self-esteem.

Be open about it, make sure he doesn't feel he's being judged by you or put on the spot. But also have your antennae up for serious neurosis. You don't want to end up being someone's shrink or sex therapist.

Of course you're curious as to whether he's a virgin. I think anyone would be. But I would be more concerned about his lack of relationships at the age of 50 and his insecurities to be honest. Anyway, for the love of god don't even think about asking such a loaded question by text. I know I'm old and nobody (but me it seems) communicates through conversation any more, but even so. Bloody hell.

@Kevinbaconsrealwife no but have been quite touchy hand wise and he was quite tender about it. Though he was definitely following my lead and I instigated the hand holding

I think its ok to want to know but your thinking about it as weird is rather odd.

Also, once you have that information - if you manage to find out without offending or scaring him, what does will it actually do for you? Do you want to continue date someone you consider weird?

@fivetriangulartrees i got teenager vibes after our last date as he kept saying he had butterflies. But in all other aspects he is very much adult

I agree OP I wouldn't fancy showing the ropes to a virgin of any age, let alone a 50 year old. I'd also be worried about his inability to navigate the emotional side of an adult relationship.

However, I really dont think I could ask him out right.

I don't think you've got enough information at the moment to be worrying about this. All you really know is that he hasn't had a serious relationship before. That doesn't automatically mean he's a virgin, and even if he is, I'm not sure why that alone would be a deal-breaker.

People reach middle age without long-term relationships for all sorts of reasons: shyness, caring responsibilities, low confidence, throwing themselves into work, bad luck, or simply not meeting the right person.

What matters more is the person he is now. Is he kind? Honest? Emotionally available? Do you enjoy spending time together? Those things are far more predictive of a successful relationship than whether he's had previous partners.

If things continue and intimacy becomes a possibility, then a conversation about sexual experience can happen naturally. But at the moment I'd be inclined to take things slowly and judge him on his character rather than on assumptions about his past.

In your situation I would be curious as to whether or not he was a virgin, but there’s no way I’d ask. What you have to consider is - what difference will it make? Will you stop seeing him if he says he’s a virgin? If not, then there’s no point in asking.