Search Results: should i ask him out relationships

Going to be 30 soon & ask myself why I’m incapable of being in a relationship with a man, people can say that I’m picky but I don’t fully believe I should take all the blame. Female friends I’ve had in the past seem to get dates easier/are okay with putting out & some have unintentionally made me second guess my looks, as they seem to have it easier yet other people have told me I’m equally/more attractive than they are. The last time I “dated” someone was when I was in my early twenties & I’m glad that ended because this guy felt like settling. It justifies that love isn’t blind & it’s better to be alone vs being in a mediocre relationship. I know I’m not all that but I feel like I should be able to attract quality men, all my life I feel like I’ve been invisible to men. I’ve never been approached in person by a guy I’d like to date (don’t count dating apps) & the very few times someone told me that a guy found me attractive (normally a guy I also thought was attractive), they never told me directly & it was always word of mouth.

I feel like I am cursed, that last person I saw in my early twenties was through a dating app & that’s how I’ve met all of these men I’ve met up with. The apps are continually getting worse & they’ve always had a bad rep, getting matches are never an issue it just fails to go anywhere for a number of reasons. And sometimes when I’ve met guys in person & it didn’t work out, there’s just something about them that doesn’t live up to my expectations (even though they look like their pics). I’m unsure if my dating logic is unrealistic, dating apps are the only way for me to meet people & don’t understand how I can be this old & haven’t been in love yet.

The last thing I’ll add is my lack of sex drive, masturbation doesn’t do anything for me & I haven’t had sex since I saw that person back in my early twenties. However, it’s known that some women need to be in a healthy relationship in order to have that *sexual desire*.

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.