Thats sad. Casual, heres my number, and then leave it. What I say may sound weird to some, but you can actually be cool and nice to women without any second thoughts. A: Rejection can be tough, but its important to accept it gracefully. But I will also say I met one really great boyfriend while working. He didnt have any way of knowing that his asking me out was going to be such an issue for me, but it still made work awkward and scary for a while, and I did my best to avoid him from then on. I got asked out by a male repeat customer around my age who had always been polite, nonthreatening, was quite nice-looking, and very interesting to talk to. JovanHuttonPulitzer #SaveAmericaFromSocialism on Twitter: Unless we want to rely on eHarmony to produce the next generation, you have to take advantage of opportunities that present in the real world.. If you are really interested and you think this guy could be something really special then there is a gentle way to go about it. OP: I think most people can tell when there is some genuine interest going on. to flirt with a cashier What would think if one of your employees asked out a customer? Your best hope here is to have a random encounter with her in a more social setting like a bar, where it is a lot more socially acceptable to offer someone a drink/phone number if they indicate an interest in you. The guys I know that routinely hit on female retail/service workers do it in the blink of an eye the second they see a pretty face. He was also very cool when I turned him down and he kept coming into the store, albeit maybe a little less frequently, and chit-chatted like nothing had happened (except for my red face because my face is my own worst enemy). Scan this QR code to download the app now. This will help reduce any anxiety and make it easier for you to get the words out when the time comes. And heres my story to support that: back in my retail days, I worked in a shop that primarily catered to women, and men coming in tended to get a bit of special attention since they were something of a rarity (and often needed a little extra help from the employees). Im in the camp that thinks its OK to politely ask someone out even if theyre working, but obviously many other differ. Meeting someone at a party (or going to a movie, while were on the topic) are not especially good first dates when youre attempting to get to know someone better. They have been married for almost ten years and have three year old twins. Im gonna join the dont do it! train. Even if she's busy on Thursday, or does not share your interest in this type of event it's a first step. Make sure you aren't unconsciously seeking self-validation of some kind.