It seems that there are quite a few users here that feel like it's NEVER appropriate to hit on a woman while she's at work.

I've never seen this be a issue IRL. I flirt with girls ALL THE TIME while they're at work.

Granted, I'm in my mid 20s so most the girls working in retail, customer service and fast food won't be too far off from my age but they generally seem pretty receptive to some light flirting.

If I see a hot girl working the drive thru I have no problem with going for her number. The worse that ever happens is I get a soft curve but pretty often I can get the number and some free food, especially in the hood.

If you're not being creepy about it, I personally don't think there's any problem with this.

Back when I used to work as busboy there was never a shortage of drunk and /or old women that would say all types of aggressively flirtatious left field shit. I would just take it as a compliment even if I wasnt attracted to them. Same thing when i worked sales.

If women can hit on us in our workplace, why shouldn't we be able to return the favor?