Should I tell my friend I like him?

[pinksunsets]

He broke up with his very long term girlfriend 2 years ago. Around the same time his mum died. He hasn't dated anyone since then. I recently saw him on Hinge so it looks like he's ready to start dating again but his profile says "figuring out my dating goals" when asked what he's looking for (the other options are short term, long term etc) which is dating speak for not ready for anything serious.

Should I make a move now? I've always had a crush on him. He actually asked me out before he met his ex but I was young and stupid and said no. We've been friends for many years. He's a really good guy and while other men post-breakup might just start shagging around I don't think he's like that and even if he starts dating casually I think it's likely he'll end up in something serious.

On the other hand, he might just be dipping his toe in and really not be ready for anything serious (while I am) and I could be setting myself up for heartache!

Oh God, I think this is what I have to do. The worst thing is I don't drink so I have to do this stone cold sober...

OK well at least you know you won’t overdo it and embarrass yourself! I’m vicariously excited for you 😂

Haha, very true! Trying not to feel sick at the idea of doing this for real...

How are you going to do it and what are you going to say/message?

I'm not sure yet but will definitely do it face to face. What if he tells me he's got some dates lined up on Hinge? Do I still tell him? I mean obviously not if he's dating anyone seriously.

Just do it now before you overthink it. "Saw your profile, want to get a drink? I've regretted saying no before and want to see what might happen."

Well you’d just say OK that’s cool. Let me know if things change

(ie. “I am not into being one of several”)

Seeing his profile on Hinge is the perfect 'in' for you.

Hey, I saw you on Hinge. I'm on there too! Maybe we should go out on a date, haha, but I'm not joking.

Men have to do this all the time. Men suffer the embarassment of asking people out and getting rejected. It's one thing I wish women got more comfortable doing.

Just think about how to do it.

You saw him on Hinge, so you could just say, "I saw you on Hinge" (Shows you are up for dating too) "Do you fancy going out sometime?"
That keeps it light. If he says yes, suggest doing something (not just a drink) - a gig for a band you both like or a physical activity you both enjoy. Then you can get a sense of whether he is still interested in that way. You could hint that you regret the answer you gave him last time.

If he says that, I might give a cheeky smile and say, 'Can I join the queue?' It gives him a clear message but it's joky so if he doesn't respond well, you can pass it off as banter.

How long would you have to wait to do it in person? I’m with others that say messaging saying you saw him on Hinge is the perfect way in! It’s relevant and appropriate and more importantly you can do it TODAY rather than wait to see him in person!

Yes! Just message, ‘Hi Bob, I saw you on Hinge. Do you fancy a drink/coffee/cinema/whatever?’

Thats all you need to say. It doesn’t need to be a big deal.

Take the chance but be prepared for it to end the friendship x

"Remember that time you asked me out and I said no because I was young and stupid and didn't know what I wanted? Well, I've done a lot of growing since and I do know what I want now. Fancy giving it a go?"

Do it. Better than living with regret.

Could you go in with ‘the one that got away…’ angle

if he’s chatting say you always wondered/regretted about turning him down

Go for it, OP!!! I actually did the same and asked a friend out a few years ago- it didn’t work out as hoped, but we are still really close friends so put it this way, I didn’t lose anything.

It's not hard, all you need to do is like him on hinge for starters - get it in ASAP.
See what he does about that, if he likes you back or asks if you mean it ir just joking, say you mean it 😉

Do it and then report back to us ;)

I'd just message and ask him to go to the pub sometime and then see what the vibe is like once you're hanging out together...

Yes you still tell him. If he's interested he'll drop the hinge dates in a heartbeat.

I once told an ex I'd regretted not kissing him the last time we met..

It had been many years since we were together and a few since we'd seen each other.

😊😉

Good luck.

Did you ask him out in person or over text?

Ha, let's hope so!

I feel like it might seem a bit out of the blue though to not see him for ages and suddenly ask him out? Over text would minimise the sting of any rejection though!

Oh definitely over text! Imagine doing that in person then it going wrong 😱 or arrange to see him when alcohol is involved and get flirty.