How to approach dating a virgin?

[confusedlady10]

I’m a single mum to a 6 year old and have been single for 5 years. I decided to put myself out there, and have been talking to this 31 year old guy for about 3 weeks. We have video chatted practically every night for about an hour and get on like a house on fire. He’s a sweet kind person. We live hours apart so if it were to become serious we would be long distance.

We have a first date planned for the end of the week. However, I spoke to him yesterday and brought up sex and preferences as we hadn’t really touched on the subject and he’s not a very flirty person. Sex is really important to me as I’ve been in relationships with bad sex before.

Then he briefly said the last time he did anything sexual was with his ex a year ago (they were together for 3 years and she broke up with him due to him refusing to be a Christian after she found her faith) and he said he doesn’t do one night stands.

However today, he admitted that the reason he was so awkward about the topic and hadn’t brought it up before, is because he’s actually a virgin, and may have a medical condition which could require circumcision and feels awkward talking about it. I replied saying him being a virgin doesn’t bother me but would at least hope sex is possible and works (in a lighthearted way) as it would be a deal breaker.

He replied saying he understood and sent me a morning message. I replied with the same and apologised in case I had offended him. (Waiting for his reply).

Would this be a dealbreaker for you, and how do I approach the subject further with him? I’m worried about wasting time in a relationship where sex won’t happen but don’t want to offend him and really like him too!

I think you’re jumping the gun massively. You haven’t even met this guy!

Yes but if he doesn’t have sex ever then I am wasting my time even going on a date if we are not sexually compatible from the start.

Omg why do women get themselves in these situations like throw them back there are millions of men, what a waste of your life.

Why compromise right off the bat? You deserve not to have to.

Not sure what advice people can really give you here - only he knows the full details of this medical condition and whether it affects his ability to have sex or not. Although it would be rather odd for him to seemingly seek out a relationship in the knowledge that it couldn't progress physically before having an operation. Surely if he does want a relationship, he'd have been more proactive in getting that sorted?

That aside, it goes without saying that he's probably very anxious and nervous about things progressing that way with you. It was a big step for him to even tell you that he was a virgin, as there's a lot of stigma around that at his age. However, the more you continue to bring this up, the more likely you are to scare him off.

Just take things slow and don't put too much pressure on him - no pun intended. I'm not sure what your intentions with this first date are, whether you're wanting to sleep with him already. If you are wanting things to progress quite quickly, and quicker than he's comfortable with, chances are you're not really well suited.

Just depends whether you're prepared to be patient and understanding with someone, or would ideally prefer someone more experienced and confident.

The condition sounds like phimosis - which I had and was circumcised for very young. If it's that he definitely can't have sex without an op first; in severe cases even erections are painful, and sufferers avoid them.
Some PPs have made good remarks - why invest so much, being gentle. Some very practical things though. There's a middle of the road between saying "tough, goodbye", and being so gentle and sweet that you say nothing about your needs:

• You need to find a few things out. I was also a virgin until late. There's his medical condition, and there's also a personality or psychology element. Many men would have done something about this earlier, what stopped him? Other than not having PIV sex, how is his libido, is he curious, does he fantasises, does he fancies you?
• Good sex depends on good communication (or so I constantly see here!). Here you can be understanding about his (lack of) experience, and gentle, but also, clear that you want openness from him. If he hide his anatomy - that's not a great start! You two should be able to talk without embarrassment about what it is exactly, what is needed, how far a long he is in getting the medical care he needs, is there a waiting list... When... If he's evasive about all that how are you going to communicate about intimacy?
• The way you talk, you are - to an extent - already invested emotionally. Provided that he is with you on the communication, you could open up to him about how you might be intimate until his medical condition is sorted out - if he's been in a three-year relationship, presumably he has been close to his partner. You could decide that sex is not limited to PIV, or at least, that that can wait.

It sounds like a non-starter to me. You say he lives hours away from you. What’s the point?

Someone who only has sex with deliberation would not be a problem for me. It’s my style actually.

The medical condition is the complication. If he has not already sought treatment, he may have no interest in resolving the problem. I would want more information. Has he simply been stymied by bureaucracy or has he just ignored the issue because it doesn’t bother him?

So, he lives hours away. How would that look practically with your child? Do you have free sitters that are happy for frequent overnights?

Or are you hoping to move in your very own cock(or not)lodger asap? How would that impact your child?

You said good sex is important to you. Even if he has this op (why has he waited soooo long??), he won't have a clue about sex and probably too old and sensitive about it to learn. Do you REALLY want to be teaching a 31 year old how to have sex?

There are plenty of decent guys with working cocks and less hangups out there, and likely live a lot closer to you. I'd gently suggest you let this one slip away.

So just don’t go on the date. He’s already told you he’s a virgin, has had a three-year relationship without having sex (so he’s clearly not a highly-sexed person), plus he has a medical condition which may require circumcision. Plus he lives hours away. Sex isn’t important for him, and it is for you. He’s not the one for you.

I would cut your losses OP, if he'd wanted to have the condition treated he would have done so by now. If it's phimosis he will need to be circumcised and to fully recover to be able to have sex. And as a pp said it's not possible without the op. If you are set on meeting at least have this chat first to establish his condition, if it's not phimosis and is a psychological problem you may still have a long road ahead.

Being kind here, it sounds like this is just a pen pal. You are lonely and chatting away, sharing and hearing very personal information with a total stranger.
Be very careful and keep your boundaries and standards high.
Realistically, if he is hours away and you have a child, him being a virgin is the least of your worries

There are plenty of decent guys with working cocks and less hangups out there, and likely live a lot closer to you. I'd gently suggest you let this one slip away.

Can't argue with this @Ncforthis2267 !! OP, there don't seem to be many positives to the current situation.

I married a man who was a virgin when we met. He was in his 30s too.

If my husband and I ever slit up I would never date another virgin. Ever!

Too much hard work, too stressful and it took years to get him to stop being selfish in bed (and even now he has his moments) because it was always about him and his feelings. Urgh, I have needs too!