I go to this restaurant/bar with my dad every Friday, or whenever we want really. There is a waitress there who is very attractive. I know that waitresses and waiters are supposed to be nice and work for their tips and such. Though, she flirts with me whenever we walk in. I haven't noticed her doing this with anyone else.

Here is where the problem lies. She's the owner of the establishments niece, and a waitress. I love eating at this place as its a ritual with my dad, he doesn't even let me pay for the meals, but I am really attracted to her. I know it can go both ways and I wont know the outcome unless I ask. Though, I can't imagine what would happen if it went sour. It would be awkward for me to go in there and be served by someone who I went out with, and I couldn't really look the owner in the eye. Which would ruin the whole environment for my father and I.

I will admit I get really nervous when it comes to asking females out, but I feel like this one could get complicated but be really awesome in the long run. I constantly catch her looking at me, not just our table, though I still can't tell if its her being nice because its her job. Though, I noticed that she goes out of her way just to get our table when we do go, possibly just because were great customers. 

I'm going on a trip next month for two weeks. I was going to wait until after I got back, to see if she asked about me, and to kind of get a feel for the situation until then. I would really love some advice on how to approach this situation. Thank you.
user
I'm attracted to a waitress at a restaurant/bar, though I don't know how to ask her out. I'm on a trip and I want to get a feel for
assistant
I go to this restaurant/bar with my dad every Friday, or whenever we want really. There is a waitress there who is very attractive. I know that waitresses and waiters are supposed to be nice and work for their tips and such. Though, she flirts with me whenever we walk in. I haven't noticed her doing this with anyone else.

Here is where the problem lies. She's the owner of the establishments niece, and a waitress. I love eating at this place as its a ritual with my dad, he doesn't even let me pay for the meals, but I am really attracted to her. I know it can go both ways and I wont know the outcome unless I ask. Though, I can't imagine what would happen if it went sour. It would be awkward for me to go in there and be served by someone who I went out with, and I couldn't really look the owner in the eye. Which would ruin the whole environment for my father and I.

I will admit I get really nervous when it comes to asking females out, but I feel like this one could get complicated but be really awesome in the long run. I constantly catch her looking at me, not just our table, though I still can't tell if its her being nice because its her job. Though, I noticed that she goes out of her way just to get our table when we do go, possibly just because were great customers. 

I'm going on a trip next month for two weeks. I was going to wait until after I got back, to see if she asked about me, and to kind of get a feel for the situation until then. I would really love some advice on how to approach this situation. Thank you.
user
I(M22) Dont know how to approach F(20) about a waitress at a restaurant I go to.
assistant