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

Unusual, yes.

None of your business though...

No. (And the people who do that usually don't insist on an STI test, do they?)
Given the circumstances, I think OP and her potential boyfriend will take it slowly.

Never shagged anyone fairly early on that you don’t know all that well in your twenties?!

Comfortable, confident and capable aren't necessarily linked to experience. The worst sex of my life was with a man who obviously thought of himself as a good, experienced lover but he wouldn't take direction and it just felt like he was doing all the moves he did every time to every woman. On the other hand, I really enjoyed another occasion where I knew I was significantly more experienced, because it forced me to take charge and do the leading - that one wasn't any more than a fling but it taught me a lot about what I like to do and having the confidence to do it.

Ultimately compatibility is the most important c word. Comfort, confidence and capability all come with time regardless of the starting point.

Also I don't think any of them are major "concerns". Sleeping with anyone for the first time always carries the risk of underwhelming sex. If he's so lacking in confidence that the sex is awful then you don't have to do it again. Cross that bridge when you come to it.

If you can't trust someone's word, don't go out with them.

How could one be sure anyone is a virgin?

You're the silly one if you'd try to insist on a virgin getting an STI check.

I would be uncomfortable with this situation too.

Sex is very important to me and I need a partner who is comfortable, confident, and capable in bed.

You’re not a bad person for being concerned.

Yes I absolutely would be weirded out a bit. I think most people would find that weird if they’re being totally honest. You’re not a bad person or a weirdo for thinking that’s a bit odd.

I think you could ask, but you would have to go about it with genuine sensitivity and accept it might not go down well. Tbh, he will probably tell you himself if he is a virgin.

Maybe I’m a bitch, but I do think no serious relationships by that age is a bit of a red flag. To me that indicates there’s something very wrong.

Are you one of them @shuggles ?

Agreed. Because this will show up at some point. Maybe not right away, but down the line. Do you really want to be the training wheels/guinea pig. I can tell you from experience that it hurts.

I would be more concerned about him not having had a serious relationship by that age tbh and would probably walk away based on that rather than wondering about his sexual experience.

So, if you like him, have sex with him and see how you both feel afterwards.

I don't think it matters if he's a virgin at 50 by circumstance. I'm around that age and have only had one sexual partner. I suspect I'm in a minority too. I'd hate someone to be put off me by lack of experience if we got on well.

It's unusual, yes.

If you woukd judge him for it, would be less likely to want to continue the relationship because of it or would in any way let it affect you then that's not very nice of you and possibly means you'll be one more to add to his experiences of "brief things that don’t materialised as he hadn’t met the right person"

If you like him, and he's a good person then it doesn't matter so you don't really need to know. If you really are his first then you get a jackpot prize - zero risk of STDs, zero risk of HPV! And you get to teach him what to do to make your body delighted. But asking him about it will only make him self-conscious and would be unkind. You don't have to shag him if you don't want to but if he's inexperienced there's an easy way to get him more experienced.

Nope.

Dont ask him. He will tell you if and when he wants to.
It’s unusual but not a disaster imho. One of my best friends is 50ish absolutely lovely and a virgin. He’s just never met the right one.

No no no no - are you mad? That is totally inappropriate.

What if you got a text asking about your body count as he was trying to decide if it was too many.

Don’t be silly.

Unless you’re naive enough to believe every man who tells you, you don’t need to bother with an STI check, you can still insist on one without asking about history.

The check is the OP’s business. Anything else is not.

Exactly. A shy, inexperienced man could make a much better long term partner than a cocky player. Give him a chance unless you are just very shallow and judgemental yourself.

He's entrusted you with some very personal information, mainly that he's painfully shy and that has affected relationship opportunites, he clearly feels safe to tell you this, i would keep an open mind he may surprise you, still waters run deep.

I dont think hes a virgin he could have a serious kink that women dont like,.if it were me id want to know why his relationships ended and does he want a serious relationship...does he have a mortgage and a good job or is he living with mummy...if hes never had a relationship that doesnt bode well

Do you not think that if he is inexperienced he is likely to be a little nervous and you drawing attention will put additional pressure on him that wouldn’t be there if things happened organically ?

Some people would say you've no right to know, others would say that if you're sleeping with someone, you do have the right to know their history. For example, if 2 people were both virgins but the woman was post menopause, they might decide not to use any protection, if neither partner had had sex for decades, this again might affect things in terms of STIs (before anyone snaps it's still not 100% safe, ok, but most people would think the risk levels are very different if Mark was sleeping with 10 people on an average week, or if he'd only had sex with his virgin teenage girlfriend decades ago).
And if someone was a virgin, or didn't believe in sex outside a serious relationship,you might want to do things differently, or take a bit longer before deciding, because it could mean that person has a totally different set of beliefs to you.

No.

It’s uncommon. But not impossible.

I would suspect he has severe confidence issues, or neurodivergence and perhaps mental health problems because of this.

That being said, you don’t need a reason to not pursue anything further with him. If you’re not feeling it. End it. For his sake.