It would be weird, wouldn't it, to contact a man I like more than five years since I last heard from him?

[wallflowerchild]

He's a man I used to work with. I always liked him and I think maybe he liked me too.

I've seen people on MN say that if a man really likes you he'll always make a move, however shy he is. So that suggests he didn't like me.

But, we worked together and he was an over thinker, always second guessing himself. I can imagine him panicking that it would be sexual harassment in the workplace if he asked me out and I said no.

But then, even when we stopped working together he didn't. But neither did I. We both still work for the same company but different branches so we never see each other.

I'm worried that if I get in touch now after all this time it'll look like I've just run out of other options and I've finally got around to him. But I never had any other options, I just never had the courage.

For all I know he might not even be single anymore.

I was wondering if I just send a breezy "Hi, long time no see, how are you?" type message and then depending on how/ if he replies ask if he wants to meet up, would that be weird?

We always got on really well and I miss him.

I say contact him. What's the worst that can happen? This happened to me a few times and I thought nothing of it. And I know of a couple of people that did this and they have now been together for years, so you never know!

Read OPs posts.

Good plan and try not to think about him.

G’ah, this is absolute rubbish. Maybe he isn’t interested but that has nothing to do with the fact that she chased up rather than him. I had a drunken thing with a guy I met randomly at a university club social. We swapped numbers, I was the one to call him a day or two later. 24 years on we’re married with 2 kids (and another on the way). I can’t believe that in 2025 people are still peddling the old chestnut that women should be passive in potential romance 🙄

@wallflowerchild Gah - you people throw the towel in early! IMHO until you hear from him you don't know - I'd definitely give it more time - he could just have a lot going on and if he doesn't want to send a 3 line reply - he might want a bit more time to compose something longer. I know - I'm an optimist but... that's my experience from writing to penpals for nearly 20 years. If you haven't heard back in a month, I'd send another message - she who dares, etc.

What do you have to loose?
Life is too short, just do it. That one message could potentially change your life!

How unbearably smug. I can’t believe you even included your original post, just so we could be extra certain you were in the right.

Would you like a medal?

What did you say in follow up & how did he reply?

I'm actually embarrassed for you.

I certainly don't think it's true that even shy guys make the first move all the time. They usually have some mental block they can't get over.

Personally in your situation, easiest way would be to approach him on social media. You can likely find out if he's single or not and you can easily knock up a conversation on there. Don't let anyone tell you it's weird. You only live once and you get to an age where you don't care what anyone else thinks about what you do anyway. Go for it.

She went for it. It didn’t work. She’s over it.

Hahaha!!!! What a dickhead response!

Honestly wtf , do you make a habit of pointing out when you're right? 🤔💩🙉

Admittedly part of me is still hoping that he's just really busy or he's staring at my messages thinking 'does she actually fancy me?' and trying to think of a way to ask me if I want to meet up.

But I know that's unlikely and I can't keep waiting and hoping indefinitely. It's probably best now just to assume he's not interested and move on.

Hey love - you were bold, you were brave. You decide what deadline makes sense to you in terms of a response. Personally I think a week MAX, and then you know, which you wouldn't have known without trying. But set your own boundary and move accordingly. What's for you will not go by you... something even better (someone?!) will be around the corner.

@SaintGermain do you want a gold medal? So unhelpful. So yes, gold medal for unhelpfulness in the Self-Righteous Olympics!

It isn’t weird at all OP - I did this in 2010 and it had a successful outcome

good luck !!

I dint answer when the door bell rings hug j say

GET IN TOUCH !! - ITS NOT WEIRD!!

it worked for me in 2010 🙌

Yes move in, at least now you won’t be in a position in another five years time thinking if only you had contacted him.

What have your message interchanges looked like so far?

It's not weird. Send the short, breezy message and see what happens but don't get your hopes up; five years is a long time and he could be happily married with kids by now. Live life with no regrets!

Edit: I just read the update that you contacted him. Well done. At least now you can move on if he doesn't reply. I wouldn't wait too long pondering on whether he will reply or not. You can only think "what if" for so long but you've given him the opportunity now and if he hasn't replied I think it really is time to move on and hopefully you'll the closure you need from being brave and trying.

I think if he was interested you’d know by now, he’s likely married or something, I’d have tried to find him on social media first to see if I could find out. You’ve tried he hasn’t replied, maybe he still will, but at least you know now.

This is total bs. Absolutely send a hi, what's the worst that can happen? He ignores you..
If you don't do the lottery will you ever win it? Hell no.
Get on and do it, all the best.