Will I be able expected to DTD?

Age comes into it if she prefers men 10-20 younger than she is. It's not a coincidence that her previous relationships have been that young and she finds a man 5 years younger OLD.

perhaps do something together (4-5 hours) involving a shared interest that isn't a dinner date or staying overnight. To get to know him better, and broaden your relationship. See if your connection grows or shrinks before you commit to going somewhere overnight.

(And share the cost.)

When you said OLD I thought you meant he was way older than you not 5 years younger than you.

It doesn't look like you fancy him and maybe your preference is for younger men which is fine. In that case you should end it and stop stringing him along.

Jeez went straight into it 😂

If you don’t fancy him then stop seeing him but definitely don’t have sex with someone you aren’t even attracted to .

This^

You aren’t sure. Best to not go away with him until you are.

Seems very soon to be going away with someone for an overnight stay.

Also...why is he paying for your taxis home?

“jay55 · Today 00:09
Agree with pp it’s the wrong order. You can’t go away for the first time you do it, what if it’s shit and you can’t escape. What if you have no sexual chemistry and it’s all awkward and you can’t leave.”

This with bells on. It’s a bit odd that you’ve always gone for considerably younger men and you say that your previous relationships have been abusive. It may be that this guy is different since it sounds as if you’re changing some patterns but there’s no need to rush anything and plenty of reason not to. As another PP said - if this was right for you, you would have said yes, not posted on MN for advice and having sex for the first time when you’re away sounds like a very bad idea.

It’s only been four dates. It’s too soon. The fact that you are even questioning it shows that you are not ready go out with him for a few months before you decide these sort of things should just evolve and happen naturally not be forced. There’s no rush.

Maybe you don't fancy him or some instinct is warning you off?

You don't know them from a can of paint after 4 dates and definitely not 2. I wouldn't have shagged anyone as early as that. I know there are stories on here where people have said they slept with their husband on the first date or after meeting them in a bar and everything worked out and they're happy but I couldn't have done that myself.

How long in the past have you waited before DTD with the partners that ended up abusive? General advice would be to take that amount of time, and triple it. That way you know your feelings are sure and you aren't getting spun by special treatment etc.

Agree with pp it’s the wrong order. You can’t go away for the first time you do it, what if it’s shit and you can’t escape. What if you have no sexual chemistry and it’s all awkward and you can’t leave.

Do not go on a mini break with this guy. He thinks that paying for taxis and a hotel gets him a shag. You will be in a strange environment and potentially vulnerable with someone you hardly know. If he realises he isn’t going to get his way he coukd get tricky. Pay for your own taxis (or drive) from now on - I know some women like to be treated - but it often comes with a price tag! Obviously you don’t have to have sex eith anyone you don’t want to, but he doesn’t sound like someone who slwsys sees it that way. Tske care

Christ! 4 dates is nothing, you barely know this man!
A hard no from me.

Age doesn't come into it.
You need to feel ready for an overnight trip and you are not.

Get to know him a lot better.
You might never be comfortable with him - he might not be a long term prospect for you.

Go away have a good time, but have an open discussion on separate rooms if you do not yet feel comfortable with sex. IME having sex and actually sleeping in the same room are in any case a different thing, so it might be good at this stage to have the opportunity to go back to your own space. If he is the real deal he will understand this. If you have been out of the game for a while, you do need to slowly get back into it. More intimacy over the coming weeks maybe but go at a pace you feel comfortable with?

In your late 50s you may be lacking hormones that inspire your sex drive. If you're n HRT, you may need testosterone. Otherwise you may need some oestrogen & progesterone if you're not on HRT. I would recommend speaking to the menopause specialist at your GP practice.

4 dates is nothing! It would feel too soon for me. Plus this dating bit and anticipation is often the best bit, I'd prefer to make it last longer.

But.. if you don't fancy him, don't string him along.

Don't overthink that part. Sometimes it takes a while to warm to someone or maybe you juat don't fancy him?
Either way, don't go away with him just yet. Seems far too early and if he doesn't accept it then he wasn't the man for you as perhaps he was only after sex. Being that you've been on a fee dates probably not though. Some men won't bother if no action on first or second date if that's all they're after.
Ultimately don't feel pressured, just do what you're comfortable with.

I've just clocked this properly. You're, say, 57 and you've been dating men who are aged 37 - 42. Lord! 😵‍💫

And your current beau is 52 and you don't really fancy him because he's a bit old 😳

After dating men who are so much younger then you, I find it a bit weird that you're struggling to express your preferences to the 52 year old

Do you think you might be a bit confused about relationships?

Well, I think being smitten after four dates is a bit of a red flag, to be honest, he barely knows you. Really, you are at the getting to know each other stage.
(I just realised someone else above me said the same thing when I refreshed the screen).
I would be wary, I ditched and ran after a scenario where everything seemed wonderful (and I did like him) but after a night away, he got too intense too quickly, and really I should have seen the little red flags before that.
[Edited to add: yes, mine was lovebombing, gifts, paying for things, and going towards the politely controlling, it was dawning on me that whenever I suggested a place to go, there was a reason why we could not go; and then when I said no a couple of times, he created an emotional chaos by questioning my commitment - to what? I barely knew him really)

It all feels a bit too perfect, him wooing you and paying for dinner and taxis. A bit like love bombing and a hint of controlling things.
I'd go very slowly, look to be paying your own way on future dates and see how he responds to that. If he doesn't like you being an independent woman, it doesn't bode well.

Staying over night is more intimate than sex in my opinion. Take the pressure off by having him round yours for an evening and see where things go

You don't have to. If going away for a night or inviting him into your home seems too intimate then stick to dates outside of that and see how you go. Just because something is expected it doesn't mean you have to go with the norm.