I work at a hotel that has a restaurant attached. For a long time there has been a waitress that comes over to do the room service so I've seen her a few times very sporadically (sometimes a month without seeing her). We said hello and chatted a bit maybe once, but never anything more.

Today I'm hanging out by the front desk when she comes over to chat with one of the front desk guys. Out of nowhere he tells her that I've been asking about her. I start to blush and she calls me out on it, so I say yeah, sure I've been (I haven't at all). He then asks what she's doing tonight. She says she's going to a bar and asks when I get off. I tell her I'm off at nine. She's off at seven and says she'll wait for me. She leaves and I'm like WTF.

Right before 9 she calls the front desk to tell them to tell me she's in the restaurant. I show up and she's sitting at the bar with a guy she works with and a girl who I assume she works with as well. Here's where things get ugly. She's 23. I'm 20. Here, you're not even allowed to sit at the bar if you're not 21. She said I'm "like a baby" to which I remembered on seddit to agree and amplify so I said, "Don't worry, my bedtime isn't until 10." She laughed at that.

She told me they were eating some food before going over to the other bar, but didn't seem to know what to do since I couldn't sit with them. I was thinking of suggesting sitting at a table, but I wasn't even sure the other place would let me in and she seemed dead set at sitting at the bar anywhere. Things got weird fast since she was sitting at the bar and I was just kind of standing behind her. I thought back to seddit and realized how beta this is to just stand there while she eats with her friends. I needed to do something because this was getting awkward by the second.

So I try to leave for the first time. She says she feels bad and reengages me by asking if I go to school and we talk about what I'm working on (I'm a film student). She asks if I work tomorrow and I tell her no, I'm shooting, but I work Saturday. She replies she doesn't work again until Monday. So like a boss I just pull out my phone and say "What's your number?" She gives it to me, and as I say goodbye she says she'll think of something all ages for them to do (I guess I'm stuck hanging with her friends) and reminds me one last time to text her.

What I did right: Agreed and amplified, played it cool, didn't wait around too much, number closed.

What I did wrong: Didn't start living until after August 18, 1990.

How should I proceed?