Ahh gutted, why is it always the way :(

[Pizzaholic33]

So I've got a male friend from work, we've hung out once before, we've hung out again this evening and spent 4 hours together, I felt a lot more relaxed as I'd had some alcohol, which I don't usually have.
He talks to me at work loads, the 4 hours literally flew by, it was really interesting, deep conversation and we also had a laugh.
He told me he's been single for 7 years.
He told me I'm basically the only woman at work he talks to/sees out of work.
He seems up for meeting again.
Yesterday online our conversation did get slightly flirty. I wasn't initially sure I fancied him but I honestly really do now.
I guess he doesn't feel the same, he hasn't made any moves but neither have I.
We literally have everything in common, we've both said it.
It might be because we work together, but it's a massive organisation and we don't work in the same department, we're rarely in on the same day.
He's applying for other jobs to leave soon.
I've got his number but I won't text him or anything.
He's the one who messages me on Teams like every day and it did get slightly flirty online yesterday.
We've only met up twice, we've not even hugged or anything but I think it's never going to happen :(
I think it's too late now :( don't even know what I'm looking for, just support, I'm slightly drunk.

Me too. Some men are just hopeless and need more than hair flicking and eye batting, some need straight talking and clear instruction.

What a bastard. Lots of red flags here. Run for the hills. You deserve so much better for yourself.

I would say just follow your instincts. If you get a feel that he's not interested then leave it be. Don't go chasing him around or fish for him to ask you out.
If he's not flirty enough or how you expect him to be at this stage then he just sounds like hard work. Hate guys that bang on about their ex's too.
If he's interested he will show it. You can be flirty in your responses without putting in much graft but let him graft.

You don't need to rush it.

If it's going to happen, it will.

It sounds promising. Think about it in the morning sans beer goggles.

This can definitely be interpreted as him trying to find out whether you would welcome him asking you out!

I am seeing positive signs in your interactions with this guy OP, but of course I could be totally wrong (sorry if so for terrible advice and false hope).

I think with him you definitely need to allude more transparently to your feelings and flirt more openly with him, to nudge him towards being confident enough to ask you out. Assuming from your posts that you'd rather he made that move than you.

It's 2024, not 1824. You don't have to wait for him. Is your entire experience of romance based on fiction?

'They' don't need to read every message, the computer is literally doing it as you chat. Key words and phrases will ping up, DH had to fire 2 people just before Christmas for inappropriate chat on Teams. It wound up as gross misconduct.

Oh FGS, just ask him out for coffee/a drink / to see an exhibition or something you're both interested in. If he says no, there's your answer. If he says yes, go for it.

I am also a bit drunk, hence suggesting minimal pussyfooting, maximum bravery!

If I can tell you anything in the whole world it is not to get involved with a colleague.
Wait until he's left at least

You’d be surprised, all it takes is a SAR or an investigation.
I once had a colleague who was sacked, but when they were conducting an investigation into her conduct they pulled up all her Teams messages. She had sent me some unprofessional messages bitching about someone. Luckily I knew better than to use Teams that way, so they were one-sided on her part, but it was mortifying to know the person they were about had seen the messages and I worked with her for another 3 years.
Just don’t do it. Especially if it’s flirty. It’s all fun and games until things turn sour, someone complains, someone submits a SAR, and then everything comes to light.
The way to think about any written communications at work is would you be happy for it all to be read by IT, HR and your manager? If not, take it offline.

This is a load of bollocks. I know of 3 women who in my 20s I really fancied. I was a really shy bloke, so didn't directly ask them out but thought Id given enough signals that they'd pick up on. All three of them years later told me that they'd fancied me but thought I wasn't interested.

If you like him, ask him out. It's the only way to be sure. it's a lesson I wish I'd learnt years earlier.

So… he was going to ask you out…

DH and I were friends for almost 2 years before we got together and he liked me from day 1 and at first sight but we are both massive nerds.

I am coming at this late but I would suggest just being being super friendly, super nice, and if he picks up on that then run with it.

Good luck!

Why don’t you just switch up the current invitation cycle and suggest dinner? You drove past this interesting looking Thai restaurant and would love to try it - is he interested in coming with you for the evening? You don’t have to say “date” or “well, do you fancy me then?”

Yep I would go with something like 'There's a new [whatever cuisine] restaurant that looks interesting' sort of thing too
I think the talk of sexual harassment sounded like he may be wary of being too forward as you both work in same organisation

EDIT: Hadn’t RTFT but see lots of other PPs have cautioned re using Teams. Stick to WhatsApp. Good Luck OP!

Typically I’d caution against relationships with colleagues as it can be very uncomfortable when they end (I know from personal experience!!) What’s the phrase - you don’t sh@t where you eat….

However you’ve mentioned he’s looking to move elsewhere so wait until he leaves and then I’d go for it and ask him out. What’s the worst that could happen - he says no? If he’s moved on, you’ll not need to worry about bumping into him in the corridor and it being awkward and at least you’ll know exactly where you stand by asking him directly. Also, I actually think men quite like women with the confidence to make the first move. I suspect he’ll be well up for it and who knows, it could lead to something special or just be some good fun for some time.

One tangential point - please be careful what you message on Teams. Organisations do monitor these platforms and often have ‘trigger words’ that will flag correspondence to IT. The last thing either of you want is a disciplinary for misuse of company equipment/technology and your line manager being privy to every detail of your messages back and forth.

op, I think this one’s dead in the sea. You’re right that if he were interested he
would have made a move by now…. another thing that sticks out is “he’s been single for 7 years”

why?

This one stinks… let if float by.

It’s 2024, just tell him you like him. No one plays games anymore waiting for the other person to make the first move.

Give over you dafty! These are the words of a nervous man who's keen but too scared. He's put this out there hoping you'll then be the one to message first. He's telling you he's bad on WhatsApp to have a pre prepared excuse incase he embarrasses himself and makes himself(in his eyes) look stupid. He's isn't prepared to make the first move, because to quote yourself, surely if you were interested after 2 months you'd have already made a move?

We did go through a phase of texting on WhatsApp but it kinda died off, but now it's just teams all the time. Kinda conscious of that though now..
With regard to the 7 years thing, not sure why that is tbh.. to be fair I have another colleague I don't know as well, but he said he's been single since 2017 too, and he seems like a very nice, decent guy, maybe just not met the right person.

We have a mutual colleague who is thinking of asking a girl in his department out so I think the comments were more aimed at that really..

Fortune favours the brave. There's nothing to lose. Go for it!

I am a little put off by how he said his exes were 'hard work', however I guess this was 7 years ago. I am more of a chilled, laid back personality, but that's who I am I guess and I can't change it.

Honestly just stop hoping but doing nothing about it. Ask him out. Just be bold about it. Either he is also doing the same as you and your all just walking in circles round each other or he'll say no and then you can move on.