Should I let him ask me?

[AllTheFours44]

Hi, I’m hoping for some input. I’m completely clueless about dating in 2022, having been out of the game for so long. And let’s face it, the game has changed beyond recognition since my hey day…

I’m in my mid 40s, divorced with one primary aged child. Have had a recent foray into OLD, with a mixed bag of results; ghosting, dick pics, being approached for all the usual weird and not so wonderful stuff I had half expected from my reading here on MN. I lasted 2 weeks before deleting my account.

There is, however, one last man standing who I had been talking to via WhatsApp prior to binning off the app. He has been nothing but sweet, respectful and someone I’ve wanted to get to know better. I brought up the possibility of meeting as I was weary about falling into a texting ping pong and then meeting and being sparkless in Seattle. He said he was just about to ask me when I suggested meeting up. We had a date, went really well and he made it clear he wanted to see me again.

My time is limited. Between shift work and parenting, I don’t have many opportunities to see people. I can look at my diary and see the only available dates I have for at least 2 months in advance; typically once every 7-10 days would be all I have to give. With this in mind, and knowing I had one free night in the next fortnight or so, I again suggested the next date. Tomorrow night. He was up for it and has contacted me every day since our first date last week. He has never been married or has kids. He’s a few (7 🫣) years younger. Doesn’t seem put off by the age gap. I like what I’ve seen so far.

I am trying hard not to get too far ahead of myself. But, assuming (ass-you-me anyone?) things go as well as the first time and I want to see him again (and him me obviously), I know I have, again one specific free night in the next 10 days…

So, what do I do. Do I continue to be the one to take it by the balls and suggest the next date? Of course I would much prefer that he has some oomph and pins me down for a date before we ways tomorrow night, but I think he’s more of a slow burner. Rightly so after only meeting. Do I just let it sit and let him make the next move in the hope my free night doesn’t pass us by?

I’m totally out of my depth here.

I get you want to protect yourself.
But isn't life too short for that? You are denying yourself something that could be really joyful for you, for the sake of something that may or may not be an issue.

And further, you can give yourself that pain now (which admittedly may be less than some possible pain in the future) but always be left with the 'what might have been' question.

Is a small part of your lack of availability, part of your self-protection? Are you deliberately making yourself an unattractive proposition or deliberately trying to minimise the chances of your mind forming an attachment?

But of course only you know how resilient you are.

You need to keep enough of yourself safe in all relationships that if the other person suddenly had a change of heart, you wouldn't be too wrecked. Have your own back.

You're investing too much. It's probably why you've had so much heartbreak. You're getting carried away on the romance.

This stage of dating shouldn't be scary or worrying because it shouldn't feel like it's a threat to your happiness if it goes wrong. Are you invested in lots of other things in your life? You need a situation where you know you'll be able to say 'Well, the relationships went wrong, and that's sad, but at least I have x/y/z passions to fall back on.'

You are all very wise. I’m glad I posted. I need to lighten up. I’m going to keep going and see what happens. I’m firmly in the camp of looking back and not regretting the things I did.

@AllTheFours44 howd it end up going?

An update. It’s still going! We’ve continued to see each other every week or so, as and when my schedule allows. The time in between, we keep in daily contact. It seems to be enough for him too.

We’re going away for a couple of nights for the first time this weekend in fact. For now, it’s great. He’s great. I took all the advice given here on board and am concentrating on how it makes me feel in the here and now, trying not to think about anything beyond that. If nothing else, the summer of ‘22 has been a fun time. I wouldn’t change it and am glad I hung in there. Thanks again to each of you who took the time to advise me!

Also, just to mention, he has become a lot more proactive in organising the dates. He asks me when I’m next free and, like this weekend, has organised the getaway. I think he likes me ☺️

Sounds wonderful op.

I was going to answer that when you’re with the right person it doesn’t matter who does the asking and who messages first. You just do what you feel like doing. With my bf I’ve usually done the organising because like you my time is more constrained. But I know he loves me and from the beginning I felt that he really liked me.

Have a great weekend!

Great update! Keep us posted.

Glad it's going well! Would have said wait til he asks and then say 'love to but I'm only free on X date'.
But seems you have come to grips with your schedule and slow and steady is good.

No don’t bother with games. Just ask him, if he says yes then great if it’s a no then you know. No need to sit around waiting like a sausage, if you want to go out just ask, it really doesn’t matter does it and to be honest as you’re the busy one it makes sense for you to suggest the dates.

Thats great news op, just go with the flow