To ask what you think of his messages?

[HeyMrWhite]

For a while now a colleague and I have been exchanging very flirtatious WhatsApp messages, but we don’t actually see each other a lot because he is field based and I am office based. He suggested going out for a drink for my birthday which is in a few weeks as he will be in the area. I decided to take the bull by the horns as such and ask the context of this drink/dinner. From his replies, I’m thinking I forced him into turning it into a “date date” and he doesn’t really want that 🙈 What do you think?

Sounds to me like he's genuinely up for it! Have fun

He’s up for it, but didn’t want to force it on you! He is definitely interested by that last text !!! Have fun!

Youve pulled

Haha thanks, I was second guessing it all and thinking I’d just made everything super awkward and he wasn’t actually wanting a “date date” lol. It’s been a really long time for me and I’m so out of practice with all this kinda stuff!

Yes I'd say he's keen - probably slightly thrown when you asked directly what sort of a date it was - but he recovered well by telling you how hot you looked.
Just one thing - don't do the faux modesty thing "I was not" when someone tells you you were hot - or pays you a compliment. Just say "thank you - not so bad yourself" or some such thing (although you may have done this later in the convo and I can't see it).

Naww this is cute. It's a date-date.

I'd say well done for clarifying. I'd be far more likely to be wondering and then end up wearing some weird combination of date date and friend date clothes so as not to be caught out.

@onemorecupofcoffeefortheroad I know what you mean about the faux modesty thing, and yes I did do what you suggested later on in the conversation 😄

He's definitely into you! This is cute. Good luck!

It's a date date. Feel free to dress up/look hot.

It’s a date but he’s being a bit controlling by pushing you into a position where you have to jokingly ask. I don’t like that.

I’m going to sound the inevitable note of caution, OP: sorry! When you asked the question he avoided it, twice. That might mean he genuinely thought it was a funny question (as in, obviously it’s a date), or it might mean the opposite.

Well done for taking the bull by the horns, though!

What’s the other context here? When you say flirty, how flirty? Am assuming you’ve met up in company before? Has he ever asked you out before?

And I would wear nice jeans and a top and boots or something. Casual jewellery. Wait for him to make the next move.

Definitely sounds like he's into you but the cynic in me would be slightly suspicious he was doing the usual blokey "try and keep things as casual as possible and see if I can end up with a FWB and not a relationship".

I don't know him so I can't judge but I have known so many men like that and they always try to play hard to get and keep you guessing (slow to confirm it was an actual date in the first half, like he was toying with you and trying to paint you as the chaser) and then bring the conversation back to sexual flirting ASAP.

On the other hand he could be very nice and not at all calculated! But something in me says "player"...

@churchandstate yeah that’s what made me doubt it 😬

We’ve met up in company before but that was before we started flirting. We’ve been flirting for probably 3 weeks now? And it’s been very obvious flirting, nothing ambiguous! He’s not asked me out before but yesterday was the first time he’s been in my area since the flirting began (but due to work commitments he wouldn’t have been able to spend any time with me outside of work)

And the “okay, let’s make it a date date...” sounds like, “Well, it was just a drink but if you insist...”

Sounds like he wasn't certain he'd get a 'date date', so he asked for a 'non date date' - and he's really pleased you asked.

Does his name begin with J?

He wasn’t being controlling! He asked you out OP and then was a bit surprised you asked for clarification It was obviously a date! Enjoy

Well, all you can do is go out for a nice drink with the bloke and see what happens. It doesn’t really make a difference whether it’s a date or not when you think about it. Have a nice time!

Ha enjoy the date date and don’t overthink!

But your screen background upsets me, far too jaunty for a cold November morning, please change it

He sounds like he likes you but please try and play it cool a bit more I was cringing reading what you wrote. I would have gone for the drinks and it would have become clear if it was a date date or a friendship.. I’m not trying to be mean but you come across a bit desperate in the message especially as he could have put you out of your misery and said it was a date straight away instead you had to ask 3 times... I’m honestly not trying to be mean but please OP just calm down and play it cool a bit.

@aSofaNearYou I’ve actually said to him before that I’m not into casual flings or one night stands, so if that’s what he’s looking for that’s fine but he’d be wasting his time with me if that’s the case. He said he understood why I said that but “let’s just enjoy talking for now” and that he wasn’t sure what he was looking for, as he’s got a lot on with work (he’s fairly new to the role).

I’m with @church. It’s readable either way, I think.

But well done on confronting the issue and not ending up in the gruesome situation of a US friend of mine.

The daughter of a friend of his mother had just moved to his city and his mother asked if he would have a coffee with her and tell her some local knowledge stuff. He agreed and called by this woman’s house as arranged on his way home from a post-work gym session, smelly sports bag, sweaty tracksuit bottoms, expecting half an hour in the local Starbucks discussing bin collections. Only to have her answer the door in a dress and heels with a salon blow dry, apparently under the impression it was a date.

I’m a big fan of playing it cool as I get older, OP. I would be half-tempted to have a big work deadline the next day, have one or maybe two drinks and then say you need to go. If he’s keen, he will ask you out again without the “umm...”