I'll just explain what happened today and why I decided to ask this question here. I just finished up work a few hours ago and have the next few days off. I am out of whey protein, so I decided to stop off at my local nutrition store to grab a new tub. I get out of my car and it's pouring rain, a huge downpour, most people are running to their cars or other shelter. I am not in a hurry, and I am going home to relax for the rest of the day so I don't really care that I am getting wet. I am pretty soaked by the time I get into the store that I've been to a hundred times and I know where they keep the ON Whey so I just walk over to get it. The female cashier asks if I need help and I kind of just ignore her and tell her I know what I'm getting. I bring it up to the counter and check out, she's telling me about their promotions and their store loyalty card, I hear the same speech every time I come in and just politely say no thanks. I pay for my stuff and I am not even sure why I said it, but I said "you're very cute, thanks for your help." She smiled and said thanks and to be careful in the rain. I wasn't expecting anything from the interaction, she really was very pretty, fit, blonde. She probably gets hit on a lot, and it's her job to be polite and talk to everyone who comes in the store.

As someone who probably needs more practice talking to women, I am not sure how I felt about this. Is it okay to practice on female cashiers if you have approach anxiety? I read Models by Mark Manson and he says to start off slow, eg. asking people for the time, then asking about their day, etc. It was an honest compliment that I did mean, but at the same time, why do I feel like it might be annoying to flirt with girls while they are working? Actually I wasn't even looking to get anything out of the situation, I had no intention to stay and chat or ask her number or anything, I just felt like saying it, so I did. I have seen men in public take it way too far, I like to think that I have more social awareness to realize that I am harassing a girl, or sending unwanted advances. I've seen 50 year old men at coffee shops asking the 18 year old barista if she wanted to come home with him that night, and I definitely would not want to be that guy.

Thoughts?