Would you go on a 4th date?

[LydiaHenry]

Met him online and went on a 3rd date at his house - he cooked. We get on well and he seems well adjusted.

He has never been married and has no children.

At the end of dinner I asked him how long was his longest relationship and he said ‘3 months’ - I thought I didn’t hear properly and clarifies but yes - his longest relationship was 3 months and no woman wanted to go beyond the 3 months mark. I asked why and he simply replied with ‘they don’t like it’

At this point I was weirded out and as it was late I decided to leave without asking any more questions.

He is highly educated, has a very respectful job (all verified) and from what he says he is from a normal family, parents still together, sister is married with kids.
He is 53.

He wants a 4th date and I could then ask some more probing questions but is it really worth it? I can’t think of a good reason why a 53 year old man never had a relationship last longer than 3 months.
On one hand I’m curious but on the other I feel like it is just too weird. But should I just discard without knowing?

Also I would feel uncomfortable having to ask again since the answer he given is too simplistic.

If it helps the chap I knew eventually revealed massive commitment phobia due to having lost his dad to suicide as a child. He suddenly started making hints about a habit of meeting men in alley ways 🤮 and I backed off pretty quick after that as not my cup of tea! Really sorry OP, its a minefield out there at our age. I like the idea of Sarah Beaney's dating app where people are put forward by their friends, but even that I don't knownif you can trust or not! I think I will only ever go via a more expensive and vetted dating organisation in the future!

“They don’t like it” is a bit of an odd phrase. If you like him then date him until you find out what “they” don’t like.

Sorry I've just noticed you are neutral about him. To me that says he's not the right one for you.

Micro penis or huge penis.. Curiosity would see me have a 4th date....

I will probably just request a phone or video call to ask tbh

Can’t be arsed with getting ready to go find out on a 4th date or have sex just to find out

Shame that I didn’t ask straight away as a follow up but as I said - I noticed the time and it could be a long conversation if I started asking because one question would lead to another until I got to the bottom

As for me feeling neutral about him - I’m slow and see this as a very good thing - I no longer have shiny object syndrom - when I say neutral I mean not attached yet but I enjoy the company and see compatibility but I’m not choosing a white dress and daydreaming a house like a teenager would do. I think dating older and with the online apps make people jaded like that.

It doesn't look good, so at least be wary - but if I was looking for long term I'd sack it off, as chances here of being the one to last, when he's had 30 years or more of trying, are slim to nill.
My guess is something sexual, given the short timeline. "They don't like it" could be anything from a kink, or maybe he has a micro-penis. If it's the latter, it's up to you to decide if it's a dealbreaker or if a willingness to compensate in other ways to promote satisfaction, might be enough for you.
If its the former, its clearly something he knows is odd about himself, so I'd be unimpressed if he kept that knowledge to himself until a moment where you're in a vulnerable position.

If you go for a 4th date, make it in public but where you can talk in confidence, then probe as much as you can. It will be obvious if he's hiding something, don't let him brush you off, be direct if you have to " what's the 'it' that women don't like about you?" Otherwise, you'll probably find out one way or another within the next 1.5 months, but it could be a traumatic end by then, depending on what the reason is.

You sound like you have your head screwed on properly OP! Exploring this in a way you feel safe with seems the way to go. There is a small chance he's just not found compatible people, but it's quite a log shot. If he's got everything else going for him then might be worth a punt to find out a bit more.

When you ask him, be wary of him blaming the women. Can’t all be their fault why he’s only ever had a 3 month long relationship span his entire life.

I'd definitely just give him a call and continue the conversation- just say you've been thinking about it and are curious as you realised you didn't know what he meant. Then of course, report back 😅

Yes I would go on a 4th date.

I was about to write a long reply about how unkind peoples' attitudes are about people who have never had a relationship for one reason or another... or people who feel they can no longer be honest about their lack of romantic experience for fear of said unkind judgement....then decided I can't be bothered.

If you want to judge him and bin him on such an unclear comment, then do it.

He'll probably be used to it and won't be surprised. He'll be fine but you might regret it.

3 dates in six weeks? That's pretty slow going, is that a mutual thing?

If you're not that bothered about him then I think a quick video call to clarify is perfect.
No point wasting time and effort on a 4th date just to ask the question.

Yes but he is a very eloquent person
Badically his job is about talking, writing, debating, reading

His ideas and words are literally published

So his answer is just a contradiction to all that he is / how he presents himself

I think it's important to work out if there is an attraction there.
Just because they havent had a long term relationship wouldn't be a total deal breaker for me, but I'd want to feel something about them by date 4. If you feel something there then it's still worth a bit more exploration.
There may be things in their past, insecurities, they may have been hurt and then not been able to open up to enable something longer term. We all have problems, but it doesn't scream "red flag" just yet.

You need to know what the 'it' is here, if you are interested enough otherwise to stay. I don't know anything about older men to know if this is a red flag or not.

I mean, he sounds like a catch. I'd carry on for a bit; - if only to find out what 'it' is - you've nothing to lose as you're not invested yet.

Just go on a 4th date. Then bin him if you're still not happy.

It's not marriage.

Lots of people get to 50s and not had committed relationships regardless of length ending because partners didn't like something. For me it was my job, it took me away a lot and I was emotionally and physically unavailable enough, phone contact only goes so far. It may be as someone who writes a lot is more insular and tends to be alone for long periods of time.

There are lots of reasons why this happens, it doesn't mean it's a terrible thing. And nothing wrong with a micro penis, less jaw ache and often more adventurous, men who have a larger penis tend to rely on size rather than technique.

If he is clean, intelligent, and decent to me I'd be tempted to continue for a while and look out for potential issues.

How many women here say they've been in a terrible abusive relationship for 20+ years, a long term relationship is no indicator of someone being good at partnerships.

I think it probably is something like a micropenis. 😐

I think you're right to see it as a red flag though, regardless if whatever 'it' is. There's something cryptic about his answer and the way he delivered it that made you 'weird out'. So not only is it likely he's hiding something, he's not showing good interpersonal communication. However polished his professional skills are, academics can be quite notorious for eccentricity and lacking interpersonal skills.

A third date at the guy's house? If he didn't make some kind of sexual move then that's likely related ...

Just wanted to say that my lovely but rather shy cousin had never had a girlfriend, but in his late 40s met a woman through the sport they both played. Got married when he was 50 and have been very happy ever since. Some people are late (very late) bloomers

My god how judgemental some on this thread are . We don't know why he has not had a long term relationship. He may have not been looking early on preferring to concentrate on studies / career etc . It's well known you hard to meet several frogs before someone good comes along and some people just never find their person .
I'd be happy he had no baggage tbh and if I liked him I like him . See where it goes and if he's not for you then move on .

I too am described as eloquent person in work, am told I'm a good communicator and present myself extremely well.

But asked to explain myself over my lack of romantic experience....well on this sensitive and deeply personal (and shameful?) topic I'm liable to clumsily fumble my words.

Re 3, TBF you said "why haven't you had a relationship longer than 3 months", he replied "people don't like it" and you didn't follow up with a normal conversational "what?", you just noticed the time and fled.