He told me it's good to see me but he wishes it were under different circumstances?

[Anonymous]

Okay, hear me out, I know it's probably a silly question and I'm overthinking, but I'd also really like confirmation. A guy who I'm not totally sure is interested in me told me "it's good seeing you again. I wish it were different circumstances" and the circumstances involved company business we are affiliated with. I guess I wonder if he meant he would like to see me/spend time away from the company?

[Guy13]

It sounds like he would prefer to see you under different circumstances. I guess work ties make that difficult?

[Asker]

It does :( and I always feel so unsure of his thoughts so I don't initiate a different circumstance. He seems to try to stay professional, but at times seems like he would like more. I'm hesitant to cross the line because I may have it wrong. There was a recent situation where he told me he didn't have plans for the holiday and I didn't really know where he was going with it because he kept repeating himself when I would give suggestions of what he could do. It honestly seemed like that was him "making his move" and I didn't bite because I didn't understand lol. I'm a very direct person so this is hard for me.

[Guy13]

That seemed like his invitation or “available if you are interested” move.

[Asker]

Any suggestions on how to give him a go ahead /confidence to directly ask me out or to push this along between us? Or things to look for as far as interest goes? I would love to get to know him better away from work. We were talking a bit more when we were working on a project together, but that project has recently been completed.

[JakeS00]

It means what it means. He likes you and probably wants more than friendship, but since you work together, it may go against business relationship protocols? Try to get to know him.

[Asker]

Any suggestions on how to get to know him or ask propose that to him?

[JakeS00]

You can set up a time to have a casual lunch or even dinner.