When we meet attractive singles at meet-ups, mixers or clubs, anyone is fair game. But what about when you encounter a potential match in a venue where asking someone out seems a questionable move? Recent readers have written about this very conundrum, and we weighed in:
Dear Wayne and Wanda,
I've been seeing a chiropractor for a back injury. He's charming, funny and extremely hot. I also know he isn't married or seeing anyone. We talk about our personal lives and I have found myself looking forward to the visits not just because he makes me feel physically better, but because he is such an amazing guy. My last appointment is coming up and once it's done, I want to ask him out. But then I worry maybe I'm misreading him and he's just being nice (and kind of flirty) as part of his job. Should I go for it or not?
Wanda says:
Odds are Mr. Chiro isn't deploying a grade-A bedside manner to get you into bed; he's probably just doing his job, which includes helping his patients relax and feel comfortable and safe at his clinic.
But … you never know, right? And it's the "you never know" that drives us all to take risks. If your time there is about done, why not go for it? Consider leaving your card on your way out, thank him for his time and attention, and offer to grab a drink if he's ever interested. The worst thing that could happen is he doesn't take you up on your offer. And then, hey, at least you know.
Wayne says:
Asking your chiropractor out on a date? Now that takes a lot of backbone!
Once your final appointment is complete, so is your professional relationship. (Unless your injury returns, that is …) So if you can get past any spine-tingling nervousness, go ahead and ask him out. But you should probably wait until your clothes are back on before doing so. A follow-up thank you note/invite to a date should do the trick.
***
Dear Wayne and Wanda,
For a few years, I've been watching this girl who is a server/bartender at a local place. After a lot of eye contact, we finally made some actual small talk, and on every visit since, she has come by to chat, even when it isn't her table or section. I think she's incredibly hot and funny and I would really like to ask her out. Is it wrong though to hit on her while she's working? I thought about trying to "run into her" outside of work but that sounds creepy. Advice?
Wanda says:
It is a little invasive to be blatantly picked up on while one is trying to do his or her job. I'm sure she's friendly and inquisitive; so are nearly all good bartenders, waiters and waitresses.
But is she into you? It's too soon to tell, and too soon to risk rocking the boat at what appears to be a regular hangout by potentially offending or freaking out one of the star employees. Keep up the small talk, and see what happens.
Wayne says:
Allow me to rephrase a popular saying: Don't date where you drink.
This problem afflicts many barhoppers -- they have a few drinks, meet a flirty server and start thinking crazy like, "She really digs me!" The best servers are as good at charming as they are at keeping beer from spilling in your lap. And believe it or not, some even get bored at their jobs, like most of us do, and strike up conversations to pass the time.
But the big question is, How much do you love this bar? If it's your favorite weekend dive or after-work go-to for apps and drinks, you might consider the ramifications of embarrassing this woman and yourself. If your advances on the cantina crush crash and burn, there are no more cheap PBRs or happy hour bacon-wrapped dates in your future. And heck, even if you do score a date, what happens if things blow up? Want to frequent the bar where your ex works? Either way, it will be time to find a new favorite bar, which is way tougher than finding a new favorite crush.
***
Dear Wayne and Wanda,
I think my kid's teacher is a babe and after we hit it off at conferences, we connected on Tinder. We haven't gone out in real life though and I'm on the fence. My daughter is in high school. The teacher is probably in her late 20s. I can't stop thinking about her.
Wanda says:
Don't do it. Can you imagine the torpedo to your daughter's social life if her friends find out Daddy is hooking up with Teacher? Talk about social ruin.
Wayne says:
Most Tinder scenarios are cut and dry: Go on and get your freak on. But this one is packed with ethical dilemmas for her and family dilemmas for you. If you want to keep communicating, cool. But c'mon, man -- at least let your daughter finish the class before you and her teacher graduate to dating.