Dear Urban Diplomat: can I hit on my personal trainer?

If your trainer is like 99 per cent of trainers, she’s a) fit, b) wears a Lululemon uniform that highlights her fitness, and c) is almost inhumanly positive and upbeat when working with you. Personal trainers fall into the confusing category of Workers Who Are Paid to Make You Feel Good. They are joined in that category by servers, bartenders, massage therapists, herbal practitioners, hairstylists and, um, prostitutes. While it’s not completely inappropriate to ask any of these fine professionals out, you probably won’t get very far with them (other than the prostitute).

More likely than not, you’re mistaking her professional perkiness—required to keep you motivated—for a more intimate connection. That said, I’m not lunging and squatting with the two of you; maybe you really do have smoking hot chemistry, and maybe she feels it, too. The only way to know is to ask her out casually, stressing that you understand if she’d rather not date clients (that way, you’ll give her an easy out). Most people are flattered when others show interest, but if (or when) she rejects you, it’s your responsibility to reel in your attraction. If you can’t handle the rejection and you start fantasizing about, say, puncturing her fitness ball, it’s time to get a new trainer.

Send your questions to the Urban Diplomat at urbandiplomat@torontolife.com