It’s not appropriate to ask a woman out when she’s working. Service staff get hit on all day and they’re just trying to work.

You can slip her your number if she shows up at your place of business and leave the ball in her court though. If she doesn’t contact you then there’s your answer.

A year or two ago, I got really excited about a comic book shop opening in town and got chatty with the owner. I decided to take him up on some drinks and a smoke sesh but we had two different goals in mind; I just wanted friendship (which i made clear to him) and a business I could give money to, he wanted to sleep with me. Things got super uncomfortable and branched into sexual harassment and I can’t go back to the only comic book store in my area now.

Comic book guy’s mistake wasn’t the act of wanting to get to know me or even being attracted to me, it was that I voiced many times that he was making me uncomfortable and i just wanted to be friends until it got to the point where I was worried about my safety around him. If you feel like there’s some connection, i don’t think it’s wrong to say “hey we have some great conversations, would you be comfortable with me giving you my number?”; it’s all up to you to be aware of what signals she’s giving off and how to respect “no” as an answer.

Why don’t you see how the lunch goes before you do anything. If possibly stop by their table to see how their food was. If the food and atmosphere is good, I think it would be very obvious at that point in time if she’s really digging you or not. That could also give you an opportunity to either ask her out there or give you another thing to talk about when you visit the dispensery again.

Also here’s a tip - if when you show up to their table, the friend decides to head to the bathroom for a minute, that is their way of giving you two some alone time. That’s when you should totally ask her out.

I am not seeing any advice already given that I disagree with in entirety, but as a guy with a gorgeous woman who I met at work (our mutual work), and a guy who is also oblivious to ‘signals’, I wanted to share what she’s taught me, and my thoughts on your situation.

We met when I was 36 and she was 39. I worked at a remote location, she was in the main office. My second week on the job, I came to meet everyone and do a day there to learn the ropes. We were the first two in the office that morning. I had no desk yet, so I was talking with her at her desk, and just being myself at work. Tech this, music that, what i did in my last job, how long have you worked here, etc. At one point, she asked me to show her something on her workstation, and I knelt next to her and used her KB/mouse, then stood up and resumed conversation from the other side of her desk.

Months later, she made her attraction to me very very clear*, and we went on a date. She spent the entire date teaching me, because she felt that I was an unfortunate casualty of my own design. I ignored women thinking that they deserved respect (which is fucking true, BTW, don’t forget it) and aren’t eye candy for the work day, to the point where she was sending me tons of ‘signals’ and I didn’t know. Like when I knelt next to her, she thought it meant I knew she liked me, because she loved my wrist hair sticking out of my dress shirt. But I was oblivious. She said she practically wet herself being close to me, and while I was talking, she only heard, “words words words arm hair, chest hair, beautiful hands,” meanwhile, I was like, “here’s how you get that information from the database…” work, work, beep boop. She still dies laughing at me about this.

I said people didn’t find me attractive or charming, and she laughed. She told me others at work had been checking me out too. What? Me?

We finished at our restaurant and stopped to fuel up. She jumped out of the car while I was fueling to show me the woman at the other pump stealing glances at me. I said it was my car she was looking at, and shrugged it off.

She and I have since moved out of the country on an adventure together, and she loves and hates my obliviousness. She says we ‘wasted’ months because she waited for me to act on her ‘signals’ and she was sad the whole time thinking she wasn’t my type, when I did like her, but I assumed that she was only being nice. On the other hand, she knows I’m not checking out other women (though she would love it if I did. What? She just likes knowing I’m happy, and thinks that knowing people are attracted to me makes me happy. Meh. She makes me happy. But I digress).

So I’m not advocating that you go against the advice here of respecting worker/customer boundaries. But it might be useful to examine if you might be similarly oblivious to genuine advances (signals). I never did anything to make her uncomfortable at work, and we ended up together, but she definitely wishes I had been more aware and asked her out on day one. I think there’s likely a way to ask your cute girl if you’re reading the ‘signals’ without being weird or making her uncomfortable. Lots of “I’m sorry if this is out of line,” and also, “I’ll totally understand if I read it wrong” to let her know you’re just confused and hopeful. Or hey, maybe at your restaurant is the right place! I’m on record as not being the best at this…

More funny deets: *The way I finally realized that she was into me was when she called me on my desk line and asked if we could just stay on the phone as long as possible, because my voice calmed her. After an hour or so, I finally (FINALLY) became aware the she was giggling a lot, and doing her best to keep me taking. She said something like, “your deep, sexy voice…” something, something, “makes me feel like a girl again.” Pretty blatant and obvious, so you can imagine the less overt signals I was missing if it came to that. Now, when we’re out, she loves to point out women (and guys) checking me out. She also loves to rib me about not realizing that her coming to work at my remote location with no justification was another signal. She used to email me the most random messages because she worried I was lonely at the remote location. She got a copy of my resume and used to read it at home and think about how “qualified” I was. She secretly recorded me singing to her after a date and played it for her family saying, “this is my future husband.” She drove 30 miles in a blizzard to my remote location when her office was closed to “get something done,” but then chatted with me until my location closed as well.

And I had no clue until our first actual date that the hours we had spent working together were so full of her flirting with me. I knew she was nice to me, and I thought we were friends, but I never guessed more than friendship.

Note: this comment may read like I am a male model who had no clue, but I promise that I’m just that way to her. I’m just her type, is all.

Ask herrrrr

But not while she’s working, it wld be cool if you came out when the dinner was over to ask how it went and then try to work on ur number or to ask her. That way it’s not her place of business and if she says no, she can just head out. No fuss, no muss

I’m going to go along with most of the other replies. If she’s at work, she’s being nice because that’s her job. I’ve had many men take that the wrong way, and it’s uncomfortable. Like dude, I HAVE to be nice to you. I don’t necessarily WANT to.

If you run into her in the wild, or she comes into your work, I think that’s ok, BUT be prepared to never go back to her work again. Especially if she says no.

If she’s with a bunch of her friends, I’d say to not ask them either, unless you can do it very quietly. Someone else mentioned slipping her your number, and letting it be from there. I’d say that’s probably a good plan of attack. Definitely don’t just walk up to a table with her and her friends and ask her out in front of everyone though.

I would have reminded you of the power imbalance that might be there, but since you are sensitive enough, I would say you are fine. Just make sure she absolutely knows it is fine if she says no, and that you have another dispensery you can go to for a while if she says no, just to make things not awkward. Otherwise, go for it! You cannot always meet people you like at a bar or whatever people do these days.

//Edit: Wishing you all the best!

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