Should I message him again, or leave it?

[bananasarent]

Reposted to remove identifying info..

I should preface this by making it clear that I am a massive over thinker so I appreciate most people will tell me I'm doing this here..

I went on one date with a guy I'd met on a dating app literally 2 days before 2020 lockdown. Good date, wasn't sure if I fancied him but would have seen him again. I got the impression he was keen on me. Then ofc the whole world went crazy and neither of us messaged again (after the initial "got home safe" etc) It would have been on me to do so tbf I think as he'd messaged last but there wasn't as such anything to reply to. I think I probably deleted him after a few weeks or something as I was very impatient back then too with dating! This is just the background so you know how we met.

5 years passed, I've been in relationships etc since (2 serious) and not thought much of it. I'm now single again recently and a (male) friend of mine ended up on a night out with this guy. There's a vaguely identifying reason why my friend recognised the name/person but otherwise it's a crazy coincidence. Anyway, I thought what a weird coincidence/maybe a sign as I'm single now and thought I've got nothing to lose by messaging him, asked if he remembered me and told him about the weird coincidence with my friend being out with him etc.

He remembered and we had a bunch of messages almost non stop from my first message but he was heading abroad for work. He's already dropped into conversation that he was only in the UK for 2 days in the rest of the month (not usually this busy though - back to normal in June). Those 2 days are this weekend but he's got a big event for pleasure on one day and another event for work on the next day, before he's off abroad again.

After a couple of days of messaging I made a joke about is this a pen pal thing or if he ever going to ask me out again and he replied haha and that he's back in June for a drink. He then (before I'd responded to the idea of waiting until June!) sent me a long message setting out his crazy schedule of flights etc for work. I do believe it all. We had some banter about if I'd still be available after 2 weeks etc and I'd let him know if I wanted to join the waitlist etc! It was all light hearted and he said it's not the case of a waitlist but he's literally can't go on dates but he's available in June if I fancy it. We said goodnight late on Mon night.

So.. do I now just leave it as the ball is fully in his court? I feel like if I messaged again he'd be very responsive and reply quickly (as he has done previously) but I'm kinda cautious about not creating too much of a false sense of intimacy as he's very responsive and easy to talk to. I also don't want to look too keen seeing as I reached out initially first to him and then I also ended up being the one to suggest a date! (Although I do think maybe he was deliberately NOT suggesting one as he couldn't until June..!) Maybe I could message on Fri and just check in how his week's been? I feel like I either need to message fairly soon to keep the momentum going or I need to leave it completely until he messages.. either now or in June..

Final note: Yes, I'm sure he's single, Yes, I believe the schedule issued and Yes I believe it's just a crazy few weeks and his schedule isn't always like this!
TIA and please be kind!

well it was all over a few days yes.. although I deliberately didn't message yday as I wanted to see if he reached out.. which he hasn't.. but his work event thing is now - started yday (until Fri) so also makes sense that he'll now be more busy than he was when we were messaging a lot...ohh the overthinking!!! 🙄

Oh my - I used to be the same. Drove myself mad thinking about every text and what he meant.
I think you are putting far too much on this for what it is.

Don't build up a big fantasy in your head of you two falling in love, getting married and living happily ever after. For all you know he could be a serial killer (I'm sure he isn't but you don't know this chap or anything about his life).
Not everyone is an overthinker and he is just concentrating on work and his life as it is now. You are not a priority to him, just something pleasant to look forward to in the future when you meet for a drink.

I would resist the urge to text again and if he wants to get in touch, he will.
No need to remind him, just try and relax, get on with your life, go and meet other people and then when he texts, it will be a nice surprise.
If he doesn't, then his loss and you carry on with your life.

Good luck and keep your fingers off those texting buttons 😀

I’d definitely wait for him to contact you.

I'd probably leave it for now. He's told you when he's free, send him a message a couple of days before saying "Still fancy that drink?"

haha thank you!

I would wait until June and if he didn't contact me send him a light hearted text saying he was in luck, you were still available and how about that drink.

Contacting him before then creates too much pressure and false intimacy. He is busy and I think will definitely ask you out properly when he is back.

I agree with this. If he’s interested then he’ll let you know. Don’t look desperate.

I feel most of these pp are insane and unfair on the poor guy. And so many of you didn’t even properly read the OP.

OP, you came out of nowhere with your message to him after not speaking for 5 years. He had a busy month already booked up. It’s unreasonable to think he would rearrange or squeeze you in those 48 hours that he’ll be in town, but I see you somewhat acknowledged that.

Stop overthinking it. None of this is that deep. He’ll be back and with more free time in June and has expressed interest in meeting then, so give him a chance to follow through. I wouldn’t message him again. It would be lovely if he messaged and continued the momentum, as you said, but I also think fair enough if he doesn’t as he’s incredibly busy and again, you came out of nowhere. It’s very early days, so give him the benefit of the doubt just this once and don’t assume that he’s just not that into you or that he’s using you for an ego boost while shagging someone else. I mean come on.

FWIW, if an old flame from ages ago hit me up out of the blue in my busiest month of the year, I would also put them on ice until my schedule cleared up.

I mean, she’s not even an old flame, they had one date five years ago and have barely spoken since.

The whole thing is just bonkers to me.

It's not a slight against him to say he's not that into the OP and I think only the part about him using her as an ego boost is unfair. He's not really into her right now. If he was he likely would have contacted her in the first place and be messaging now, keeping up the contact until the date. Maybe that will change afterwards if they do meet up and start seeing each other but right now all he has to go off is a date 5 years ago. There was nothing to lose with OP sending the initial message but now the rest has to come from him. There's no point trying to pin down a disinterested person.

@bananasarent the guy had and has a life before you .
June isn’t that far away . Jeeze
You sound needy . Chill out and meet him
when he’s free .