This has actually happened to me a few times. The first time was by a guy old enough to be my father. Asked me out for tacos just because I'm Mexican. So tip #1: Don't be horrendously older than her. My boyfriend was actually in my line when he asked for my number, but we had a mutual friend who knew we were both interested in each other. If you know she's single and she might be interested, ask her. Just like 'ssassin said. Do it in a casual way as to not creep her out, it'll definitely flatter her a little and she'll know your interested. If you have a friend that already knows her too, that helps like it did for me

If they are around the same age it's just fine to ask someone out. If you can wait until the store isn't busy or she is away from the register, that is best. A straight forward, "Would you like meet at (insert closest coffee shop or restaurant) later?" Then make sure to add a quick, "If you are interested; if not, I'll still be your best customer." I worked at a gas station right by 3 colleges and people were meeting up all the time - no, not me, I was engaged and a good girl.

Remember to take "no" for an answer, gracefully.

I'm a bartender, so I get asked out by custys all the time. Mostly it's just an annoyance; I tend to doubt the sincerety of people who hit on an employee (who can't escape! Hahaha). That said, I think bar staff are a lot touchier (read: extra cynical) about it than most other industries.

One guy almost got me though, and this is what he did.

I had never seen him before, though I don't think it would have made much difference had he been a polite, well behaved regular. We bantered a bit while he paid for his drinks, and he and his friend moved off to enjoy them. Before leaving, he stopped by the bar (no other custys present), handed me a slip of paper, and said something to the tune of "Hey, I think you're cute and fun to talk to. If you feel like getting coffee or hanging out sometime, just give me a call."

And then he smiled casually and left. No looking back, no awkward silence or waiting for a response.

I think this works for a few reasons. One: no pressure. He's not forcing a sudden decision on me, which is sort of rude to do to someone when they are at work and in 'professional mode'. Two: This method showed a lot of confidence! That in itself was pretty sexy. Three: it was a very mature way to show his interest without being a nuisance. If your brother's crush is 27, she will likely appreciate this.

Not saying this is a 100% success lady killer method, but I feel like it's a pretty good bet. Good luck!

It's always awkward being asked out at work because, well...you're working! You're busy.

Some general rules I'd say:

1. Don't do it while your wife is on the other side of the store shopping. Has happened to me. No, I'm not kidding.

2. If you're asking out someone of a different race than yourself and she says 'no' don't then make a joke about it being about race while her supervisor is within an earshot. Also has happened to me.

In all seriousness, though...

3. Don't ask while her supervisor is within an earshot at all. You never know if her supervisor is would be uptight about employees flirting on the job, so even if she wanted to say 'yes' she might not be able to for fear of being reprimanded.

4. If you're going to ask at the register while you pay, don't do so while there is a line.

5. Don't ask while the store is busy in general. It's hard to think about something like that when you're running around with a million other things on your mind, and when it isn't busy you're just more relaxed and willing to talk and get to know someone when business is slower.

6. If it looks like they might be in the middle of a corporate visit, don't ask at all. Come back another time.

7. Just the general rules for not being creepy. Don't get pissy if she says no. Don't lead in with inappropriate sexual comments. Don't spend 20 minutes leering before you ask. Etc, etc.

8. I think slipping her your name and number, and briefly saying that you think she's really cute and fun, and you'd like to hang on with her some time is a good idea. Less pressure. Less being put on the spot and having to decide if stopping to accept a date or give him your number is okay, or if it might get you in trouble if your boss sees or if another custy complains.

K, I'm with a lot of the girls, except the slipping the number. I worked at a chain toy store where there would be newspaper sales people in the store. So this guy had been shooting the shit with me for almost my whole shift at the service desk. We had a line, so I jumped on a register. Seeing this, he broke down his booth thing, then grabbed a hot wheel and came through my line. He asked for a piece of paper, which I gave him, and then he half crumbled the paper and put it on my counter. I asked him if it was trash and if he wanted me to throw it away. He told me it was his number and kind of mumbled an invitation. I apologized and told him I wasn't interested because I was in a relationship.

That should have been it, right? Not so!!! Mr. creepy proceeded to sit outside my work until I left. Then, my ride wasn't there, so my coworker waited with me because creepy sat there staring for the full half hour it took my boyfriend to get there.

So my advice echos the stuff already said. Do it when not busy, be confident, but also be direct. Be prepared to hear no. I actually recommend he practice with other girls first, haha.

Update: He's coming over here tonight. I'm going to help him rehearse and go with him to the store in question at slow time [around 8 p.m. -- I'm in the Pacific time zone, so if you're in other time zones make the mental adjustment] to help buck his confidence up when he asks her out. Will post further as developments occutr.

YAY!!!!!!!!!!!!!!!!!!!!!!!!!!!!

Awesome!! Always glad to hear a story with a happy ending for all. =)

I'm a little late to the party, but I would also add, that thanks to this site, I now know NOT to approach the lady in question with a hand full pennies talking about my wealth.

Yay! Congrats to your brother.

I really enjoyed this thread. I hope the guys around here found it helpful.
Maybe we should do more of these on the right ways to interact with retail workers socially.
I know I've heard plenty of stories about friends and family asking to use employee discounts, and not understanding why that's a big problem.

You don't. Not in my opinion. Hitting on/asking out a person at work is essentially backing them into a corner. They are on the clock, they are paid to be nice to you, they cannot simply leave in the middle of their shift if they are uncomfortable. In short, they are not in a good position to say no, and it will almost always be uncomfortable. You might also get her in trouble if a manager sees her talking to you and decides that she is goofing off. If you run into her outside of work, great, go for it. Don't ever hit on someone who is on the clock. IMHO.

On a personal note, I have been hit on/asked out while at work. I do not appreciate it. At best, you are oblivious to the power breakdown in such a scenario. At worst, you are deliberately taking advantage of it.