Will I be able expected to DTD?

[Paladinski]

I’ve met a really nice man OLD after meeting several very disappointing ones with red flags all over the place.
I’ve not had any red flags from him at all and he’s a gentleman, we’ve had four dates and each time he’s arranged a taxi for me home and paid etc, he’s very complimentary and has told me he’s smitten with me, without being smothering in any way. It all seems a bit too good to be true to be honest because in the past I’ve made very poor choices with men who have been abuse and destroyed my confidence, so I’m extremely cautious.

He has suggested we go away for a night, his treat, for our next date, but I’m nervous as we haven’t had sex only kissed so far. I’m in my late 50’s for goodness sake - I was never this nun-like in my past!

I’m Im guessing he’s expecting intimacy so why am I suddenly so shy? Any advice anyone- sorry this should probably be in Relationships rather than AIBU.

Sorry meant to add, I’ve got round this by suggesting an air bnb with two bedrooms. Though I haven’t told him yet that I’m planning on using one of them, I don’t think it’ll be an issue though

I’m wondering if I’m struggling to fancy him because he’s close to my age and all my previous partners (which haven’t worked out I hasten to add) have been anything from 10 to 20 years younger than me, so he seems so much older than them, even though he’s 5 years my junior. I’m just not used to ‘older’ men, not good on my part I realise.

You shouldn’t be struggling to fancy him! What are you doing woman???

it’s nothing to do with age

If you don't feel like having sex, you don't have to. He's not necessarily expecting it (I had some lovely nights away when I did OLD, sometimes separate beds, sometimes same bed but not always sex) but you could broach the subject beforehand. If it's the only reason he's taking you away, it's not a great sign.

If you don't fancy him after 4 dates it's time to call it, I think.

I wouldn't let anyone pay for me at this stage. IF I couldn't afford something, we would do something cheaper!
I don't think this applies later on, by the way, if one person is richer than the other.

It does seem a bit soon for me, but my DH and I did this not long into our relationship, we went on holiday for a week, but slept separately, he had absolutely zero expectations or pressure and to be honest I fell in love with him on that holiday, that was 12 years ago now and I've never looked back.

I'd just take sex off the table, say you are happy to go away but you feel it is too soon for intimacy, then if you do go and he's a perfect gentleman you may find yourself wanting to take things further, or it may just be the next step in your relationship while you build up trust.

But if you are at all unsure then just say no, you'd prefer to wait, in fairness there is something about 'scheduling' intimacy that puts me right off to be honest.

I think it's heavily implied that "going away together" means sex imo. If it were me I'd decline, until you're already at that stage. He sounds lovely, so I'm sure won't be difficult about it (and if a person IS difficult about this sort of thing then they should be binned off anyway).

Re not wanting sex yet, I don't think that's a problem at all, so long as you know you fancy him. Idk where this notion has come from, that everyone must be gagging for it by the 2nd date? I think historically this hasn't been the norm or the expectation. And for me at least, as well as the hormones not being the same as when I was 14, I'm less trustful, more body conscious, more tired, more distracted by responsibilities, on more medications than when I was younger... all of which reduce my sex drive. It's not abnormal in itself.

I would wait a bit longer. 4 dates in and then a weekend away seems a bit full on. I thinknI would be more cautious.
I used to be fine with a one night stand in my 20s.
But worked hard on myself and boundaries and I would want to know a person better I think than 4 dates worth. I would however change up the dating to do something different to your usual dates and see if you still get on in a different setting.

Oh ! Well, maybe that doesn't bode well for sex

This

How is him paying for your taxi making you safer?

I think you and he need to have a conversation about this, explain your fears, he is probably a little nervous too. That's quite normal at any age when you haven't been intimate before. The important thing is good communication and to be kind and loving to each other. I presume desire is there, that is a good start, just don't expect too much. My wish is that you are pleasantly surprised!

First of all, talk, gently and thoroughly. You need reassurance and so does he.

Good luck.

10-20 years younger than you? Yuk

yes I was going to say the same. "smitten" after 4 dates? Be careful OP

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.

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

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.

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)

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?

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.

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.

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.

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?

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.