Whats happening here? If he's not into me, why drag it out and not shut me down?

[Anonymous]

me and boss flirt all the time and just get along well but i think I've messed up a bit. We were joking about a photo he doesn't like of himself and i replied "for what its worth, i think its cute" and he just replied with a load of the arkward face emoji. I asked him what he meant and he just changed the subject and continued chatting. I feel like he's constantly baiting me and then not really following through. If he's not into it, why doesn't he just shut me down?

[EnnyT-S]

It may be that your boss realises this is an asymmetrical relationship, and that he shouldn't be flirting with you. It's not illegal for a boss to try and seduce a person working under him, but it's unethical, in the same way it is for a teacher to try and seduce a student.
You haven't done anything wrong, but my advice is to find someone else where you can be sure the attraction is for reasons other than the person's temporary social position.

[Asker]

Why do you think he just doesn't say this to me or just ignore me? Without this i feel like its encouraging it more...

[EnnyT-S]

Hard to say, not being him, but I'm guessing he's just trying to kid himself it never happened, and therefore he has nothing to be ashamed of.

[historectomy]

he's your boss for one and two he could just be shy, he may be scared to pursue any further and there is no telling if you pursuing would drive him away

[Asker]

Im quite wary of driving him away or potentially making him uncomfortable and this is probably the most direct I've been. I didn't know if he was just embarassed about the photo or if he thought it was cringy i said that. Just wish i knew what he was thinking haha!

[historectomy]

i'd say best bet is try to be sure if he likes you or not then just honestly ask him