I Have an Plan to Ask Out a Client. My Friend Says It’s “Stalkerish.”

Good Job Photo illustration by Slate. Photos by zimmytws/Getty Images Plus and BartekSzewczyk/Getty Images Plus. Good Job is Slate’s advice column on work. Have a workplace problem big or small? Send it to Laura Helmuth and Doree Shafrir here. (It’s anonymous!) Dear Good Job, I’m a 25-year-old woman and I work at a doggy daycare. It’s the perfect job for me. I’m in an intense masters program and it lets me make some money while I play with dogs (and also clean, which I like doing.) Here’s my issue. I have a major crush on one of the (human) clients. He’s been bringing his dog here the whole time I’ve been working here (about six months). He’s not wearing a ring, and I’ve never seen someone else with him. I know asking him out at work wouldn’t be appropriate, but I have another idea. When I check his dog in, his profile, including his address, comes up. I recognize the neighborhood. It is not near the daycare or near my house, but it is near my school. I am thinking that when my classes start again, I could make it a habit to spend time at a really nice park in that neighborhood that I know has a dog park. He did mention before that his dog loves the dog park, so I think chances are high I could run into him. And then maybe I could ask him out then. My friend thinks this would be like being a stalker and that I still shouldn’t do it. But I have a reason to be in the neighborhood, so I don’t think so. What do you think? —Dog Walker With a Crush Dear Dog Walker With a Crush, I mean, look, I love a dog-related meet-cute as much as the next rom-com fan, but I’m with your friend here. Let me be clear: I think it would be creepy to use the address that you got from your work to go to a dog park in his neighborhood, and I can’t imagine that your job would be thrilled if they found out that you were using customers’ information in this way. In fact, I actually think it’s less inappropriate for you to casually ask him to get coffee sometime the next time he drops off his dog. So why not go for it? If he agrees, then great. If not, then you have your answer. One other thing. This is a bit outside the scope of this column, but I just want to gently offer that having a “major crush” on someone who you’ve seen a handful of times and only interacted with on a professional basis is maybe something to sit with. I’m not challenging you on whether or not you have a crush—it’s clear that you do, or at least feel that you do—but you barely know this person, and it’s possible you’ve constructed a whole fantasy around his life that is far from the truth. I would hate it if you were letting other romantic opportunities go by the wayside because you’re so fixated on the “what if” of your doggie day care customer. Or I could be completely off-base here and you’ve had several in-depth conversations with this guy and feel like you know him—in which case, I take back what I said. But I felt I would be remiss if I didn’t at least bring it up here. Either way, I’m rooting for you, no matter what happens. Good luck. —Doree Classic Prudie I was engaged at 22 to “Patrick.” We never married because before the wedding, my sister “Cindy” revealed that she’d slept with Patrick and was pregnant with his child. He denied it, but I called off the wedding anyway. Never miss new Slate Advice columns Get the latest from Prudie and our columnists in your inbox each weekday, plus special bonus letters on Saturdays. Advice Workplace Jobs