Should I pursue or give up?

[leosauntyeggie73]

Bloke at work who I find attractive and who ticks a lot of boxes for me. He is the same age and is single. I am a secretary and he is resources manager so our paths cross usually daily and I email him when I need resources for a particular job.

Our emails have been friendly then jokey then mildly flirty but although I have been a bit more direct than normal they haven't progressed into anything. When we need to discuss something over the phone then he is v relaxed and chatty but face to face not so much. He is quite stuttery and uneasy.

He is also on a dating site I am on and we have chatted - very limitedly - on there - he doesn't seem to be on much tbh.

I am now at the position where I am starting to feel slightly foolish about it all. I am 46 years old and I guess what I am wanting advice on is whether to continue with the friendly flirty stuff - banter about common interests etc or whether I should cut my losses- draw a line under it and move on.

Ask him out for lunch.
What have you got to lose?

@bakesalesally I know it sounds silly but I don't want to lose respect by misjudging it all x

Honestly, if you’ve chatted on a dating site then he knows you’re single and looking; and if he hasn’t as much as suggested “getting to know each other better outside of work” or something in messages on there, it doesn’t sound like he’s interested. Could be all kinds of reasons, from knowing you’re looking for something different to what he is, to not wanting to potentially mess up a situation with a colleague. I’d just let it go if I were you.

You sound lovely. Withdraw from him. He sounds like a needy dick.

I would honestly steer clear of dating colleagues. Look outside of work.

He has opportunities to make his move, but he doesn't. What does that tell you?
He could ask you out, on the dating site.
He could ask you out, by email.
He could ask you out, in person.
He doesn't.
Perhaps, just in case, you should say to him, when only the two of you can hear, that if he ever asked you out for a drink, you'd go. But you wouldn't want to make him feel awkward by asking him out.
There's nothing to lose - if he's not interested, he won't ask. But it might give him the confidence to ask you, if it's only shyness holding him back.

Thanks everyone. I always feel as if he's not interested but then he pops up asking about work stuff or phones me. Then he's all smiley and jokey and when I respond he shuts down. I think he's throwing me titbits lol

Give it up. He could have made a move. He hasn't.

You have to go in to work every day and see him every day, I would leave it.

It sounds like he likes you as in he thinks of you as a pleasant co-worker he is on friendly terms with. But he doesn't want to date you or have sex with you. If he did, he would have asked you out. (It may be that he doesn't want to date a co-worker rather than that he finds you unattractive, of course).
So carry on being cheerful and friendly, but look elsewhere for men to date and have sex with.

Dating co-workers is a bad idea in itself, especially if you run into each daily.

On the other side of the coin he could be very bad at flirting or anxious that you’ll turn him down! Men are perpetuated as the ones who should ask women out by a patriarchal society but some are just too shy or nervous! In addition if he’s in a management position he might be worried about making a move on you for various reasons including being accused of work place harassment if you turn him down. I would say in this instance, if you want to move things forward, you will have to be the one to make the first move!

See a lot of PP are saying "if he was interested he would have made a move by now" - but what if he's thinking the same thing about OP?! Maybe he's shy and worried you'll knock him back? That would explain the shyness/stuttering.

I'm not sure how closely you work with him or if it's ok to date colleagues, but if it is - give it a go, ask him for coffee. The worst that can happen is he'll say no, it might be awkward for a little while, then you'll be no worse off than before.

Beachandcocktails, if he was interested, he'd respond when op flirts back, but instead he shuts down. She describes him as smiley & jokey, but when she reciprocates, he pulls back. That says to me, he's not interested in following up or doesn't think good idea because of work.