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.

Noooo. That is so rude and intrusive.

Does he live in his own place?

We want men to be respectful of women and not just use them for fun or 'experience', but they need to have had sex before we meet them?
So if they get past a certain age before having met someone in the right circumstances, they are not a suitable person with which to have a relationship?

You describe him as kind, tender and you are attracted to him. What gas gone wrong with our society that someone's possible lack of sexual exerperience would be a red flag. You say you're shy yourself, I would have thought this could be a great relationship.

yes I was thinking about checking he'd been checked......you too of course

There are PLENTY of guys who have lots of experience in the sack and are not good lovers. If you like him I’d see how it goes, the risk of him being shire in bed is the same as someone who isn’t a virgin I would say

He may well have sex in his teens and 20’s but not had a ‘serious relationship.’ I wouldnt say a relationship is anything under a few months. He then may have gained weight and been very shy/self conscious and not had a proper relationship in the era most people start dating/settling down.

I wouldn’t necessarily assume he’s a virgin.

This with bells on! If you like him and it instinctively feels nice, just go with the flow.

So obviously a confidence thing. Well done him - and quite something to confide in you regarding long term relationships. Please don’t destroy his new found “zing”. It’ll be sonething you’ll discuss further down the line.

Is he successful in other ways? Does he have lots of friends, a good career, healthy habits and financial stability?

It would be totally useless to make a virgin have an STI check!
(I realise you can catch some STIs without 'going all the way', but those ones are usually diagnosed with symptoms e.g. herpes and warts).

I agree with not asking by text. However, she's dating him so it's not 'none of her business'. And I say this as someone who lost her virginity much older than average. It's not something to tell everyone, but if you're starting a relationship, it's relevant.

I dated a man in his thirties for a while and think I was his first sexual partner. I was maybe five years older than him.

It was awful. He had no idea what to do, the language he used was juvenile....he finished before I started....he was over- enthusiastic like a puppy dog and once tried to set an alarm for 2am when he thought he would be ready to go again - I vetoed this!

People might say "ooh, you can teach him what you like", but a) I literally never had the chance, b) I don't want to, I want a man to know what he's doing to at least some extent.

And he started talking about moving in with me after just a few weeks, and I had a one month trip to Australia set with my work and he was going to miss me so much he asked his firm (not linked to mine in any way) if he could work on a project in Australia for that month 😵‍💫
I ended it before he crawled to the airport to see me off!

FWIW as I’m unlikely to be in this situation I don’t think asking outright or putting the ‘virgin’ label on it is helpful at all. If you are open to intimacy (of whatever sort) with him it might be nice to explore that together and creating a safe and non judgemental space for you both to do that would be pretty key. I think you should know that asking ‘are you a virgin’ or ‘what sexual experience do you have’ will likely lead to more stress and potentially the end of the relationship, which is of course your prerogative .

Not important, yes - but not to the point of having none at all? I mean I had dry spells but even then I had my urges, its quite normal?

However I would be more concerned regarding lack of relationship, not lack of sex. Though two may be connected.

OP I'm going to go against the grain and say it would really bother me if someone was that age and a virgin - I can't quite articulate why but I'd be grossed out.

I guess if you were similar to this guy it would not matter but for me it would be very, very odd. I cant say I had many partners by mid-50s but I was married for 10 years and had several relationships raging from short to quite serious, plus some one night stands and some small flings. And I'm not really sex mad, particularly attractive or promiscuous - its just normal life, by the time you get older these things accumulate. I would find it really strange if someone somehow managed not to have these ordinary experiences - at all. TBH I'd rather date some fuck boy who had hundreds in body count. At least it would be fun!

I wouldn't ask him. If he's lovely and you both really like each other does it matter?

Personally I think no serious relationship at the age of 50 is a red flag, as is the language surrounding it.

I’d assume he’s either A, a commitmentphobe who leads women on and then does a runner.

Or B, “insecurities” to me screams controlling and possessive and all the women he’s ever dated have run a mile as soon as these traits have emerged.

The alternative is that there’s something in him which puts women off in the longer term.

Either way to have never had a serious relationship by the age of 50 really isn’t the norm, and while he may be lovely, I wouldn’t kid myself that you’re “the one” although I don’t doubt he’ll tell you that he’s never felt strongly enough about anyone before, “until now.”

I wouldn’t take that as he’s a virgin. I would take that as he’s casually dated before, but not had any serious relationships. Which I do think is an issue at that age.

I think that if I fancied someone, and there was trust there, I wouldn’t feel weird about it. I mean for sure it’s a bit unusual but I’d try to be really open minded and sound about it if it is his first time. It wouldn’t bother me although it would be something different. But that’s ok

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!

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.

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!

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