Search Results: ask him out myself

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.

My girlfriend and I have been dating for 5 years and recently we celebrated my birthday. There was one thing I specifically asked for that she got me and I appreciate it. But everything else just seemed a little thoughtless.

One thing, she got me a personalized ice cream spoon. On the surface, it seems cute but I practically only eat ice cream with a tiny spoon when I’m home and the spoon she got me was a normal size. I probably won’t really use it. She also got me pimple patches from a brand I like other products from but I really don’t have pimples and the few times I’ve used patches in the past, they don’t work or sometimes make my face scab. I've told her this before since she uses patches and sometimes asks if I want to use any. Then finally, I’ve been wanting a kiddie pool to just be able to sit/ put my feet in, like the $15 kind. She ordered me one but it’s not supposed to come in for another week. Which is fine and all but this week I have off of work and I would have used it now. To me, I would have preferred to just go get one myself at the store so I could actually use it when I have time off. Or even just ordering me one that would have came in time for my birthday.

Everything she got me is sorta thoughtful but also not that useful to me. Part of me feels like she didn’t really try but the other part of me feels like I’m just being ungrateful. Gifts from her have always been like this but in the past I just let it go since I thought she was actively trying and maybe just not hitting the mark. But now that we’ve been dating longer, I feel like she should know a little better.