Search Results: should i ask him out first move

I like my boss. He is such a sweetheart! He makes eye contact when we talk, laughs/jokes with me, tries to invite me to work outings (which I usually avoid unless they're mandatory), etc. I know he's my boss, but he makes it a point to let me know he'll accept a call for help at any time of the day and wants me to call him when I'm feeling down... I joked about the latter when he first suggested it and accidentally chuckled in a sultry way, which he seemed to do in return? I felt there was some "tension" between us at that time... but that could have been my own "tension" talking.

I love that he's respectful to women regardless of looks, and I also realize that he might not be into me and is just being kind. DGMW, I'm not ugly... but I'm very aware that I'm not everyone's cup of tea... I've been reminded of that multiple times since I was young. Penelope/Colin relationships, especially ones where Pen looks more like Kate or Lady Danbury than Daphne or Queen Charlotte, are uncommon. I've also noticed my coworkers (mostly the women) acting funny towards me ever since this one time he told me he liked my hair. I can't tell when I'm liked because it's so few and far between, so I don't know if they're seeing something I'm not or just being weird... don't men compliment hair?

I made the mistake of dating a coworker while we worked together years ago; I wouldn't dare pursue a relationship with a coworker now. I've also been rejected by every guy I've ever confessed to, so I'm hesitant to put myself out there. I want him to make the first move, but I'm also worried, if he feels the same way, that he's too scared to say anything to me... so I want to try to "guide" him to me. I told him a few months back that I wanted him to "not be a stranger" with me after I quit, and he's said I should let him know when I'm quitting. "Tension" made me feel he was saying it in that sort of way, and I'm thinking of revisiting that convo when I tell him I'm quitting.