Help! I(26M) would like to ask a coworker(22F) out but I've never asked someone out in person!! Ahhhh!!!

Pretty much what the title says! Also throwaway account juuuuust in case. But here's some background:

I work as a job coach for various people throughout the county in California where I live. I've worked with various people at one store(which is a part of a major American retail chain that shall go unnamed) throughout the past couple of years I've been a job coach. Recently, I've taken to doing paperwork in the breakroom(which is another of my job responsibilities when my clients are comfortable doing the job largely on their own) on my laptop, while also checking in with the clients who work at this store.

Also recently, there's a girl who works as a manager in one of the departments in the store(I'll call her A) who, whenever I'm there doing paperwork, will spend her breaks chatting with me. Like, coming to sit down at the table where I sit specifically. She did this three days in a row last week and twice this week. And just today, A spent the entirety of her (hour-long!)lunch break just talking with me. We do hit it off pretty well... I think. She's told me details about her life that I won't go super into here, but they seemed kind of... hintish? Like maybe she's interested? Like she's talked about her type, what's going on with her dating life at the moment, stuff like that. Oh also, she told me about some little factoids about cheese and other stuff today too. It was, in fact, pretty interesting!

The reason I'm skeptical of even asking her out is... I've never really had someone who would give me hints that they're interested. Never flirted, never even been in a committed relationship before(if that wasn't obvious already) so I've got that cool lack of experience going for me. And I'm kind of afraid that even trying would make her want to not talk to me anymore while we're in the breakroom. It's probably dumb but I just can't help it.

I was going to try and ask A out today, if she wanted to grab a drink this weekend at a cool little bar I found out about that's nearby, but she had told me she had a date tonight with another guy before I could. A also said this guy wasn't her type, that she expected it to go terribly and that it was just an obligation to some friends who set them up. Buuuuut I still felt it would be kind of weird if I asked her out just then.

So, with all of that out of the way; should I just go for it? I'll be working at the same place tomorrow, and it seems that would be a great time to ask her. I guess I really just need a push or something! Or maybe some advice on how to ask her out as smoothly as possible? Or if it's all for nothing and I should just give up?? Help???

Submitted November 08, 2019 at 12:07AM

Pretty much what the title says! Also throwaway account juuuuust in case. But here's some background:I work as a job coach for various people throughout the county in California where I live. I've worked with various people at one store(which is a part of a major American retail chain that shall go unnamed) throughout the past couple of years I've been a job coach. Recently, I've taken to doing paperwork in the breakroom(which is another of my job responsibilities when my clients are comfortable doing the job largely on their own) on my laptop, while also checking in with the clients who work at this store.Also recently, there's a girl who works as a manager in one of the departments in the store(I'll call her A) who, whenever I'm there doing paperwork, will spend her breaks chatting with me. Like, coming to sit down at the table where I sit specifically. She did this three days in a row last week and twice this week. And just today, A spent the entirety of her (hour-long!)lunch break just talking with me. We do hit it off pretty well... I think. She's told me details about her life that I won't go super into here, but they seemed kind of... hintish? Like maybe she's interested? Like she's talked about her type, what's going on with her dating life at the moment, stuff like that. Oh also, she told me about some little factoids about cheese and other stuff today too. It was, in fact, pretty interesting!The reason I'm skeptical of even asking her out is... I've never really had someone who would give me hints that they're interested. Never flirted, never even been in a committed relationship before(if that wasn't obvious already) so I've got that cool lack of experience going for me. And I'm kind of afraid that even trying would make her want to not talk to me anymore while we're in the breakroom. It's probably dumb but I just can't help it.I was going to try and ask A out today, if she wanted to grab a drink this weekend at a cool little bar I found out about that's nearby, but she had told me she had a date tonight with another guy before I could. A also said this guy wasn't her type, that she expected it to go terribly and that it was just an obligation to some friends who set them up. Buuuuut I still felt it would be kind of weird if I asked her out just then.So, with all of that out of the way; should I just go for it? I'll be working at the same place tomorrow, and it seems that would be a great time to ask her. I guess I really just need a push or something! Or maybe some advice on how to ask her out as smoothly as possible? Or if it's all for nothing and I should just give up?? Help???