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

Yeah I get what you’re saying too , unless they’re players & he clearly isn’t .
You don’t think it’s possible he just has been misfortunate , & has never met anyone he clicked with ?

Absolutely NOOOO !!
Do not ask him this , seriously OP !!
I’m sure he’s not anyway , he told you he’s met women but nothing has ever materialised into a relationship.
He’s just never met anyone he’s clicked with .
If everything is going well & you like him , why fuck it all up 🤷🏻‍♀️

If he's never had sex, you can teach him to do it any way you like it. Win!

Of all the ways to ask, this MUST be done face to face. Text message is a terrible way to do something so serious.

Same here.
It's not OP's place to teach him.

You have got to weigh things up: the cost of staying with such a guy - who less face it has a good chance of being weird-is far greater than the very minimal cost of breaking it off after a mere handful of dates.

The only thing is to be kind when breaking it off. No need to explain in detail.

Ouch!

People can have sex while not in a relationship.

Huge red flag.
Sorry but it just is.

Not just being a virgin but no serious relationship.
He may very well be a nice guy, no matter, it's just too weird, OP.

You've only had 5 dates, there's nothing really to give up yet, just let him down gently.
Somebody should tell him not to mention the no serious relationship part, it just makes him sound strange.

Yes this is harsh but true.

I would agree with this.
The sex is irrelevant up to a point but if he has just been dating around and not stayed with any women for more than a couple of months, that's different.
There's nothing wrong with asking that question when the time is right.

I met someone years ago... he had a tiny willy i mean really small it could be an insecurity like that that overwhelms his head not necessarily a virgin .

@Howyoop I can't help with the virgin question, but I'm 37 and my partner is 47 and until we got together his longest relationship had been a year - when he was 20!

My shortest relationship had been 3.5 years so I can't pretend it didn't concern me. But so far so good, we work well together and I've found a good one - been together nearly 2 years which for him is basically a lifetime, and for me is still early days.

See how it goes, it might be amazing!

A bit weird but not unheard of. My brother is 42 and has never even had a girlfriend.

I would be weird if he was a 50 year old virgin. Ask him how many women he has known intimately. It might be a lot and he's playing you.

does it matter?, you can teach him

He's soon learn tho! You might be hugely compatible. Don't look a gift horse in the mouth I say....

I started a relationship with someone very like this and he turned out to be impotent. I find men are fiercely private about this and will never admit it, so probably no point asking. You’ll find out soon enough if you try to take things further.

Exactly!

Too serious an issue to gamble with your own health.

It would for me. Id not want to have a bloke who hasn't got a clue

@Howyoop yes, of course it's weird.
I would imagine he has though if he's said he's had a couple of flings.
I'd ask him. Or if it's going well and you want things to progress physically, take things a little further and see how he behaves. And how good he is.
I've had a very inexperienced boyfriend before and it was quite fun. You can teach them exactly how you want to be touched, and if he is worth his salt, he'll love it and be open to your teaching.
He'll also think you are fantastically awesome at sex!! Lol

Really?! This is a terrible idea

People can have different opinions on that, but since he's waited 50 years, he might feel comfortable waiting a few more weeks.
The point was that the person insisting on the STI test was presuming the man was lying. Why would he lie when his lack of experience is considered quite a problem?

Would you rather he had sex once twenty four years ago or not ever? What difference does it make? Either of those is better than endless use of prossies.

If you take things slowly and it turns out to be rubbish, you have invested a lot of time and possibly emotion. Better to find out sooner rather than later.

And if he’s good, you reap the benefits.

I have to say I haven’t read any of the thread so have squat all idea what it’s about!

If he’s recently lost 7 stone he may not have felt attractive or been attractive to women before hence the lack of experience. As such, he might not have the experience to take the lead. I’d be asking a bit more about the insecurities. However, you won’t know whether, once he gains sexual experience, whether that will become a problem or not. If you fancy him, then tell him that you’d like to take things physically further at his pace. You never know, he might be wild in bed once he gets going!