Is this a date hint?

[YourCoolFish]

I have been flirting with someone for quite a while. No dates as yet. We have a shared interest in watching (not playing) tennis. A few days ago, he said to me "You and I should watch a match together at Wimbledon this summer". Could never happen of course, but is this a hint at a date?

Might suggest cinema.

I didn't close the deal...just suggested via text that I was selecting films to watch, didn't suggest we watch together. He responded " that sounds nice, enjoy them" and sent a hug emoji! I just cannot tell whether he is really interested or just enjoying flirting...I am hopeless

Think the lack of jumping to suggest going to cinema suggests a lack of sufficient interest. Help!

“When a man wants to spend time with you, he’ll let you know.”

He likes you well enough, but not enough to be brave about it. I’d move on, personally.

Is that you GregG ?

I am slowly coming round to the idea that he is a bit wet. Interested. Likes flirting. (I am also aware he checks me out nicely but definitely every time we meet). But just not able to take the next step. So either I get bold or give up.

I know others sense the interest between us. That much is clear.

Sorry I may have missed it but is he single? Are you single? Do you work together?

If you ask him out, chances are you will find you end up with one of those men who lets you do all the 'driving' in the relationship, so I wouldn't, cos that's not what I want. 'A bit wet' is not for me! If you don't mind that though, or like to be the one arranging everything, then crack on and ask him out.

We are both single, yes. We met through work.

Hmm,,,,yes, you are probably right.

TBH he doesn't sounds all that interested to me but I'm happy to be wrong on that.

If you are still working together I'd can any flirting happening at work, it upsets team mates and can get either or both of you into hot water.

I’d reply ‘that sounds like a big commitment, maybe we should start with a coffee first!’

But then again I’m quite forward and that’s fight or flight for guys. Be ready for things to potentially not work out but at least you’ve shot your shot. You miss 100% of the shots you don’t take etc etc

Any winter tennis things you can go to instead, has the O2 end of year tournament happened yet?

I think I will just withdraw a little and see what happens. If nothing, then I have my answer. If he pursues, I will be more forward and ask. Either way, it's time to move on in one direction or another.

It's helpful to get some different perspectives on it rather than keeping it in my head.

I am a bit gutted it's true as I have enjoyed his company, but it's got to be more than that.

Nice thoughts, thanks for replying. I am feeling quite disappointed overall.

Guess I am just not very adept at navigating these things and fell for someone. Worried I sent the wrong signals (like maybe that I was not interested) a few weeks ago. I think he misinterpreted my being busy when I was away for a few days (He knew I was away). So maybe he is being very cautious. Or simply is wet or not sufficiently interested.

I've had a big think about this. I think he thinks he's made it clear he is flirting and has suggested meeting up. The tennis thing was only the most definite (specific event) if a long way off. I realise I really do need to suggest something definite back. If it's then a no (or not clearly a yes), I will know he is not interested. But I think he is. (or maybe i am just hopeless at this game).

Your most recent post sounds spot on to me OP. Backing off to test if he's bold enough might just be read by him as you showing you're not interested. If you suggest something firmer and sooner and you don't get a clear positive response, then at least you'll know. It sounds like you are chatting frequently and get on well so I'm sure something natural will come up soon where one of you can suggest a date.

Come on, it's not difficult.

"That sounds great, we should! Wimbledon is an awfully long way away though. Fancy going for a drink in the meantime?!"

If he doesn't pick up on this and look to set a date with you, you have your answer.

From all your updates OP you're hugely overthinking this.
It doesn't sound as though you have shown any real keeness either.
Appreciate within my culture (Caribbean) people are generally a little more forward and direct and it can be difficult if you work together & will still see one another.
Suggesting you're selecting movies to watch doesn't jump out at me that he'd suggest going to the cinema. Catching up for a hot drink and cake as pp suggest, glass of wine or dinner are all things that can be proposed as friends. You can test the vibe and then take from there.

Cinema is actually an awful suggestion for a first date. It's 2 people sat in silence learning nothing of each other. Much better to suggest somewhere you can chat and get to know each other.

Probably right!

This is my plan