Why does my 49 year old male coworker constantly say things that insinuate that I miss him or he misses me or I’m happy to see him?

[Anonymous]

My male coworker said ‘I didn’t mean to make you sad by leaving work so soon today’ on his way out and when I shrugged my shoulders and looked down to show sadness he was amused and happy. Why does he always insinuate that I miss him? But never asks me out?
he also loves to say ‘you look happy today. Or are you just happy to see me?’

[SueShe]

If your age group is correct, then we are talking about a man that is almost double your age or at least 20 years older.

He is very clumsy at flirting and you are not helping out the situation by playing his game with your shoulder shrugging.

I see it that this guy has reached his midlife crisis and is now trying to get to just about any girl that is willing to pay some attention to him. Rather than to distance yourself, you actually throw oil on the fire and let him believe that he has a chance to get into your pants.

That is not really a wise behavior. You realize that once he has obtained what he wanted, he will move onto the next victim.

[OfMiceandMen]

So you want him to ask you out? If so, you may have to flirt back a little more. He may be just flirting with you to keep things fun at work, but if he knows your interested, then he'll likely get around to asking you.

[Asker]

Oh what I would give to get to be on a man’s list of things to get around to!

[OfMiceandMen]

What I mean is, some guys take a little longer to click-in that you're interested in more than just being friends. You may have to drop some good hints. It may also be a little unexpected. I know I would be somewhat surprised if a girl in your age bracket was interested in me.

[Asker]

What friendship is there here? Flirting has nothing to do with friendship. I’m a nice person and a good listener and guys always take advantage and start flirting on and on and even bullying me but never ask me out. It’s all a big joke and I’m tired of being the punchline. All for being a nice person.

[OfMiceandMen]

Flirting has everything to do with being friendly and building a friendship. It doesn't always have to be about trying to ask the person out or get in their pants. There is such thing as friendly flirting.

[Asker]

Maybe in some men’s minds but not in mine

[Iron_Man]

Talk to the guy get to the bottom of it drop hints

[Asker]

Like what hints

[Iron_Man]

Talk about movies that have come out in the movie theater. Say to the guy that you’re dying to see this certain movie and you have really have been looking forward to that one particular movie. Say you don’t have anybody to see it with and your friends are all busy that weekend working. Any guy that’s interested in you would say oh yeah that would be great. Why don’t we go together

[Asker]

I thought you meant a subtle way to get him to expose his true intentions. But your way is really forward.

[Iron_Man]

Just get to the point if he doesn’t bite at this, then forget he’s not interested

[Asker]

That’s his job as the man

[Iron_Man]

Do you know how many times women wait around for a man to make a move and the man is so shy nothing ever comes of it. You have to swallow your pride don’t always except for a man to make a move how do you know he’s not afraid of being rejected?

[spartan55]

@asker
"that's his job as a man" 😂 okay so what is your job as a woman? Show up and do nothing? With that attitude you can look forward to being alone.

[Avicenna]

He’s interested

[Asker]

He needs to ask me out