Advice on an older man

[GracieJackson]

Hey guys,

I have read so much great advice and wondered if anyone could offer me some.

I’m going through a divorce at the moment from a man who treated me really badly (a lot of cheating!). I’m worried about dating and can’t be bothered with the games.
I have liked a man at work (he’s 51 and I’m 35) for around a year, but thought he was happily married and so kept what I thought was a delusional crush quiet.

I went on a night out with work and turns out he is separated. We ended up spending the night together, I was very drunk but it was so fun to finally have the time with him I’d always wondered about.
He messaged me a little the day after saying things like come say goodbye, thinking about you a lot, wished he was in bed with me still etc. nothing creepy, just lovely messages. I then didn’t hear from him for 2 days. As I work with him, I sent a message that just said - hey just checking we’re good? (I worried he regretted it and wanted to assure him we could forget it if he did have regrets) and he said morning, yes of course. We’re good :) and not I’ve heard anything else.

I don’t get it, is it an age thing or is he not interested??
Im away now for 2 weeks so can’t see him to understand and it’s driving me crazy. I didn’t think I’d ever let myself get involved with these games again, and thought an older man would be a lot more straight forward.

Help, am I overthinking it?

I agree with this. Tbh, unless on that night he was saying he wants something serious or some kind of relationship with you (which you haven't said he did) then I don't see he's done anything wrong. You both fancied some casual sex or you wouldn't have slept with him straight away so he probably assumes you're both on the same page.

If he told you he is separated, then I'd treat that with caution. A lot of caution. That age gap is going to become problematic in the long term too.

I agree these could be possibilities. Maybe he likes you, really is separated, but isn't sure if you are interested and doesn't want to be a creep.
I suggest you ask him out for a drink or lunch and talk to him.

Same age gap as me and my husband . Happily married for 20 years so far.

wished he was in bed with me still etc. nothing creepy, just lovely messages

Ah OP. Can you not see that this is not lovely at all. It was just sex and this makes that very clear.

If you were hoping for something a bit more than a ons, step way back now.

OP my first instinct is, "he is not separated". I hope I am wrong but I am guessing I am not. Let this one go.

I'm afraid my experience of casual sex dating is that they are almost always at least one step more married than they tell you.

Take what positives you can from the situation (you had a great night with someone you were attracted to) and move on.

Why would it be an age thing?

Thank you for the response guys. He’s def separated, I subtly asked at work and turned out his annual leave was time to deal with it.

I’m still so confused though as the mixed signals
are wild.

Dating again is honestly a minefield. I’ve found this particular man very confusing. He messaged me twice while I was away - 1 saying are you enjoying the wine and another said he liked my new pic of WhatsApp.
When I got back to the office, he was WFH, he messaged saying nice to have you back and an hour later asked to set up a call about a work query. I said I had sorted the query and he asked to video call to double check. It was pretty flirty and as I was in the office I was very measured with what I saying, but it was 30mins long and only 10mins talking work.
He WhatsApp’d my personal phone after and said nice to see you and also set up a bunch of meetings and said we needed to meet often for planning purposes.

So seems quite keen but then it’s always about work and also he barely texts me etc we don’t talk every day, it’s more every 2/3 days.
I don’t want to play games or ever guess where I stand. I also don’t want to have a serious chat about it as it’s so early and that’s no fun. I feel like if he was interested like that, I wouldn’t be guessing.
I was in the mindset of be professional etc but sex shouldn’t happen again. It’s not serving me well, I really like him and it’s not been easy when I don’t get a lot back.

We have an end of day meeting on Monday, and all I want is to kiss him or go back to his hotel etc and I think I’ll be very disappointed when it’s just work.

Oh my days- I don’t miss these emotions with dating! I feel like a crazy woman.

At best if he is recently separated you will be a rebound but of fun.
If he's not properly separated it will be even worse.
Moreover he is OLD. 16 years is a huge gap and men age very badly through their 50s and beyond. You will be giving him an ego boost due to your age, but what will you get out of it?
If it went the distance, you'd end up with a man of 70 when you're only early 50s 🤢

Sorry OP but from your update I don’t think he’s sending mixed signals at all. Hes sending a very clear message that he’ll be up for a repeat and keeping you sweet for the next opportunity

You arent going to win this one on here @GracieJackson You will either be told he just wants sex (as you already have been) or if he was serious that he wants an unpaid carer for his old age.

Thanks guys.

Time to leave it. Appreciate all the feedback.