He’s comfortable with me flirting with him, but doesn’t make a move (older man in his 40s)? He used to be nervous around me now he’s comfortable?

[KezHarris]

Hopefully he’ll make a move soon… he also unsent a message on WhatsApp.. I wonder what he typed..

He’s scared of rejection

He’s not THAT interested

He doesn’t know me well enough to make a move

Other

[DJB72]

If I remember, you work together, yes?

If he makes a move and you're not into him that way then these days it doesn't have to be you who screams "predator" or "sexual harassment" and he loses everything.

If you like him and you want to see if there's a possibility for more then why not send him an actual physical letter and - importantly these days - inform your HR manager that's what you're doing and specifically that you're ok with any response from him as long as it's legal between two consenting adults.

A lot of older men won't approach a woman these days because he can literally lose everything just from an appearance of impropriety, never mind whether he actually laid a finger on her or not.

If he asks if he can video the date, he's not being creepy - probably - he's just concerned about protecting both of you

[AviatorTom]

If you want him to make a move and he doesn't... make a move yourself. You'll both like it.

[HawkPerception]

I think it's a mix of he's fearful of the rejection and potential disgust that you might have with him being 40 hitting on a 23 year old and not knowing you well enough to know how you think or how you'd react.

[lightbulb27]

he's been burned before and doesn't want to trash his income source. he knows better. boundaries are necessary, including saying no, even if one wants or likes.

[Nik1hil]

He won't make a move..

At that Age he will look like a predator..

If you want something, you make a move!..

[Fireguy17]

he might just be clueless about you wanting him to go any further.
Guys are like that, I know I don't have a clue about that.

[Juxtapose]

You know the success rate of women asking out guys is really high.. try it yourself instead of sitting on your ass and waiting for someone to do it for you.

[bowenw]

He may not believe a 23 year old could really be interested in him.

[TheSpaceGnome]

Why do women who never make a move themselves, get bothered that the guy isn't making a move?

[jjj101010]

Seems like it is moving in the right direction, make sure u r sending him encouraging signs

[ThrillSeeker01]

Are you sure he's single? Hence the hesitation, maybe.

[syncheart]

Probably scared of rejection.

[GoodGuyBreakingBad]

He's scared of rejection.

[Nice222]

You friend zoned him.

[strateguy632]

,3rd.