I was wondering if it’s ever remotely okay to ask someone out if you meet them whilst they’re working. I don’t mean asking out a co-worker, but instead asking out someone who’s on-the-job at the moment.
I’m talking about a very nice, incredibly cute girl that happens to work at a coffee shop that I go to most days – I know I’m now rather unceremoniously going to be tagged as one in a long line of over-caffeinated guys who have had a crush on a girl that works at a coffee shop. In my defense, I’m usually quite shy and she’s struck up conversation before – and I have subsequent times – and I think she’s really quite cute (and this is odd but I learnt that she’s a recent transplant to this city from another continent and I find that quite intriguing – it takes some guts to do that to pursue whatever it is she’s going after) and would love to learn more about her.
Should I, as the obvious Office Space reference goes, just ask her out?… Here’s the real question – how do I do that without making her feel like I’m putting her on the spot in her workplace?
(Have I mentioned that it gives me a secret thrill to get letters signed with these descriptors instead of names? It’s sooo Dear Abby. I guess I’ve arrived.) Anyway, kudos for thinking this through before jumping in. It shows you’re considerate and I know I’d appreciate it if I were this gal. I think you have three choices.
1) Go to the coffee shop at a time when you know it will be slow.
Maybe as soon as they open, or mid-afternoon, or right before they close. Even better if she’s the only one working, or at least the only one behind the c0unter. Order a drink and then casually ask her out–“Saturday mornings I walk my dog along the Thames. Would you be interested in joining us tomorrow?” Bonus if you pick an activity that references something she’s mentioned before or the two of you have discussed–art museum, favorite restaurant–so that she knows you’ve been paying close attention when she talks. The benefit with this option is that you’re able to be direct, and tailor it to her availability. The cost with this option is that it may be hard to catch her alone, and if she’s not interested, you’ll hear it to your face. (But I promise if that happens, you’ll survive.)
2) Arrange some kind of group activity with your friends
Y’know, concert in the park, happy hour at a nearby bar–whatever you want as long as it’s casual and doesn’t have a strict start time. Then, the next time the two of you are chatting, mention it to her. “Hey, you know, a bunch of my friends and I are going to Jazz in the Park on Thursday night, you should stop by if you’re available. Here, I’ll write down my cell so you can call me and find us if you decide to come.” The upside to this option is that it’s low pressure for her (she doesn’t need to say yes on the spot), and it gets your number into her hands. The downside is that she may not be available for that specific time/day, so it’s sort of limiting.
3) Slip her a note the next time you go in. Yes really!
A small piece of paper that reads something like, “I’d love to take you out sometime, but I don’t want to put you on the spot while you’re at work. Here’s my number if you’re interested, I hope you call.” The nice part about this is it takes all the pressure off both of you. You’re not confronting her at work, and she doesn’t need to call if she doesn’t want to. The bad part about this is that it’s passive. I like a more assertive approach, but I know women who don’t, and I know men who don’t, so it’s really a matter of individual style.
Dude, it’s your anthem!
If it were me doing the asking, or the one being asked out? I’d go with Option #2. And if she’s not available for that specific time, try again. If she’s interested, she’ll figure out a way to make it work, or she’ll use your number to set up a different time to get together with you. Good luck, and have fun!
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