How do I ask this guy out?

[capturingdaydreams]

So I have a friend of a friend who asked me out years ago and was interested in me for a while. I'd just broken up with someone so I wasn't that bothered. Since then I've changed my mind about him. The last time I saw him he was telling me about his new girlfriend but I know now from social media that they're not together anymore.

How do I ask him out without seeming like an online stalker? He obviously has no idea I know. I haven't seen him or our mutual friend for a year.

When did they split?

Rather than ask him out directly, can you message him and say hi kind of thing?

Not really sure. A few months ago maybe. They weren't together that long.

If he asked you out at a particular place or there was something memorable about the time/conversation, message him with something like "I was just walking past x and thought of you - how are you doing?" or "I heard that band we were talking about on the radio and wondered how you are?"

I guess I could just message him with some chit chat and then ask him how things are going with his gf. He'll tell me they're not together anymore and then drop in how we should go for a drink...?

No!!! Just message and say hi
Don't say how's it going with your gfriend, sorry I just think this is very full on....I would be freaked out if I got a message like that. You know he hasn't got a gf so why not just message and say hi - his reaction will tell you what you then need to talk about surely

Sorry if that sounded harsh and you can do what you want but I think a message to say hi is enough

Btw my partner and I split January, we are not friends on fb, not connected on social media and both our profiles could be taken as single by the exterior
But we've just started talking again and in my situation he's very sorry, wants me back, wants to meet up this weekend, doesn't want anyone else
So just be mindful of that

A simple hello message would be my opinion and then take it from there
Please don't say how's it going with your gfriend when you know they are not together

Well we've been friends for many years so if I just drop him a message to say hi - as one of us has done in the past - he'll probably just assume it's a friendly thing and it won't go past a few messages.

Of course it will! If he likes you in that way. You don't need to say how's it going with your gfriend wanna go for a drink - just think it's a bit forward but as I say, it's your call.
Message and say hiya kind of thing and see what he says back - see if he's chatty, see if he's putting questions back to you, replying etc
There are loads of signs without being direct

And you haven't spoken in a year so if a guy messaged me after a year, I wouldn't think he was just being friendly - it would depend on how the conversation went
Ie if I was interested I would reply, ask questions and think this is good that this guy has messaged
You will get the vibe on his reply
Do it now lol

Are you still friends with the mutual friend? Ascertain if he is definitely single from then. Then tell the guy you are interested in, that you heard he was single and have been wonderinf about him...whatever. Give him a get out clause maybe by telling him to let you know if its too soon (re: ex). If he thinks its a bit intense, or isnt interested, he can use that as an excuse without anyone being too embarrassed.

Start a conversation and say "do you fancy a drink sometime?" - you've mutual friends I presume so knwoing he's single isn't going to be a massive stalky thing. Don't fanny about, it's the 21st century.

dirtybadger - I know he's single because he was tweeting about being on Bumble a few weeks ago so he's obviously dating again but good idea about the get out clause in case he''s not interested anymore.

dropsrainbow - I normally wouldn't go anywhere near someone who has recently broken up with someone but they weren't together that long, less than a year. I do think I need to say something to signal I'm interested as I haven't been for so long and have rejected him in the past.

category12 - If only I was brave enough!

Go on bumble and find him

Haha, I have been doing that. Nothing yet!

Just message him before he hooks up with someone unsuitable.

Good point!

Be brave, go for it

Just do it. What's your worst case scenario? He says no and then you don't see him again for another year? Go on, you can do it!

"Hey Rudolph, remember that drink you asked me for in 2012? Is it too late to say yes?"

Obviously don't call him Rudolph if his band is Dave

So he lives near you? Just message to ask him out! If he says no, no big deal, you hardly ever bump into him anyway.

So...what's the update ? X