I’ve been going to my massage therapist for over a year now – I randomly found him via an online deal and became a regular client of his almost immediately. He is amazing and we have a very strong connection. He has a Master’s in literature (I’m a writer and was an English major); he’s brilliant, hilarious, erudite, introspective, and genuine, as well as gorgeous. During my hour-long massages we spend the entire time talking with each other – he tells me about his family, his aspirations, his inner reflections, everything under the sun. Oftentimes our exchanges leave him laughing so hard he has to pause the massage. We give each other book, TV, and music recommendations, and I even wrote about him in my blog – twice – and he loved my writing. Seeing him is one of the highlights of my month. (Side note: I’ve gifted massages with him to several of my girlfriends over the past year and all of them confirm that he doesn’t talk to them at all like he talks to me during the massage.)
When I first started going to him last year, he was recently separated – he’s 10 years older than I am and has two young children. For the record, if it matters, he left his ex-wife after many years of feeling emasculated and unappreciated. At that time, he was understandably not looking to date anyone. Now, more than a year later, he says that he is starting to feel more ready to date again. He tells me about older women (in their late 40s or 50s, mostly ex-clients – he’s also a personal trainer) who ask him out after their divorces, but he’s not interested in any of them.
Over the last few months, I’ve been going to see him on weekday evenings. I’m his last appointment and he often extends my massage or chats with me while he closes up the studio and walks me to my car. This past week, he was so wrapped up in conversation with me he forgot to take my payment for the massage and I had to remind him. He later texted me saying, “Sorry if I was a chatty Cathy – you bring it out in me!”
I’ve pretty much always had a bit of a schoolgirl crush on him, but lately I find my thoughts lingering on him constantly and I’d just like to spend some time with him outside of the massage studio. He’s awesome and I’d really like to get a drink with him and talk when we don’t have a time limit (and I’m fully dressed and upright!). But I’m a client! I feel like I’m stuck between a rock and a hard place.
Bonus points – I know he loves dogs because he has a yellow lab who hangs out with him at the massage studio – and he even trusted me enough to let me walk him around the neighborhood while he was massaging a friend of mine. A genius dreamboat who loves dogs! What’s a girl to do?
Thank you so much, again, for any advice! — Touchy Feely
Gurrrl, ask him out! He sounds interested, and what do you have to lose? Oh wait, a great massage therapist, I guess. But there are others! If you ask him out and he says no and it’s weird — or if he says yes and you go out and it’s weird — you might feel too awkward to keep seeing him for regular massages. That’s the added risk (in addition to potential rejection). If you think it’s worth the risk — and he sounds like such a great match for you! — I’d tell him after your next massage that you enjoy talking to him so much that you’d love to extend your conversation beyond the massage studio. And then ask if he’s free to get a drink (or a green tea, or a bite to eat, or just go for a walk) when he gets off. If he’s interested in you (and in taking the risk of potentially losing a steady client if things get weird) he’ll say “yes” if he’s free or suggest another time when he is. From there, just let nature take its course. If you aren’t sure if it’s a date-date, kiss him. That’ll definitely answer any lingering doubts.
If you have a relationship/dating question I can help answer, you can send me your letters at firstname.lastname@example.org.