“My Massage Therapist Won’t Stop Flirting with Me”

I’ve had this massage therapist for three years now, and I have developed feelings for him that I suspect are mutual. He does house calls for just me. All of his other clients have to come into his office for their appointments. About six months after he started massaging me, I asked him to a home-cooked dinner at my home. He refused, but he said that “I can’t have dinner with you now, but I am looking forward to the day that I can have dinner with you.” He was very enthusiastic and happy when he was saying this, and he had a huge smile on his face.

So fast forward to over two years later. He has been there for me as my massage therapist through cancer, the loss of close family members, formerly chronic pain which our work together has significantly reduced, and a few other enormous and life-altering events. Needless to say, I was not ready to ask him out again throughout much of this time. He has a very intuitive sense of where I am at and what I need. He “gets” me. I asked him out for the second time just two weeks ago.

This was after he literally said that I have a “fine ass” while I was naked on the massage table last week, and he brought up sexual conversation between us, which I was fine with participating in. We do sometimes flirt, he has called me “beautiful” many times, and he has complimented my hair, my dress, my style, my sense of decor, etc., but this was very strongly sexual; he has never said something like this to me before.

He refused my invitation by saying that he isn’t hanging out in general these days. He is living in isolation two hours away and only comes into town for 1-2 days to work before going back home. I responded: “Okay. This is the first time in almost three years that I have asked you directly for a date. I’ll probably wait another three years to ask you again! I will see you on Sunday then [for our appt.]. Thank you then for making me feel beautiful and whole and even sexy.” And he responded, “And you are! See you Sunday.”

I can’t figure out if we have anything or not. He is a terrific therapist and I don’t really want to lose him in the therapist capacity. We are not sexually compatible as he has kinks that he has shared with me that I am not interested in.

I have never been happier in my life than when I am with him. Oh, and I forgot to mention: He has been single for this entire time, he has been clear with me that he has not wanted a relationship with anyone. He also admitted to me that he and I have sexual chemistry. — Conflicted yet Well-Rubbed

If you’ve never been happier in your life than when your massage therapist makes sexual advances and comments to you, despite the risk to his career and your professional relationship and despite making it clear that he doesn’t actually want a relationship with you and despite rejecting your advances for a date twice now, there’s an issue. Multiple issues, really. First, there’s no future for any kind of relationship with your massage therapist and you should stop pursuing one. Don’t ask him out again. Not in three years and not ever. Also, consider swapping massage therapy for psychological therapy – or do both if you can afford to, but I highly, highly recommend finding a new massage therapist as continuing to see one who has repeatedly crossed professional boundaries isn’t going to be helpful in your pursuit for mental well-being, and prioritizing your mental well-being right now is a MUST if you are serious that you are happiest when this guy is sexually objectifying you on his massage table. There is joy to be had out in the world, and relationships that can be mutually fulfilling, but you aren’t going to find those things with this guy, and I’m concerned that if joy has eluded you thus far, it’s going to continue to elude you until you get some mental health guidance.

The other day, while I was hanging out with a friend I used to date, I ran into my fairly-casual lover, “Steve” (whom I happen to have strong feelings for, and I’m pretty sure he has feelings for me as well). He (my ex) and I were friends before we ever dated; in fact, we ended the relationship because we were great as friends but our romance was dysfunctional. We play music together and were on our way to his apartment for a (strictly friendly!) jam session when we ran into Steve. However, I’m not sure if Steve understood that it was just a friendly meeting. He seemed a bit surprised to see us together; it was the day after Steve and I spent a really beautiful night/morning together. We haven’t spoken about it, but I was texting him yesterday and he seemed a bit down… then again he’s also been stressed at work, so it could have been that. Things are still evolving between us, and I want him to know that I wasn’t just running off to romance somebody else the day after we connected so deeply. It’s really not my style. I’m not sure how to bring it up or go about it, as I’m not sure what his interpretation of the situation was, and we’re not exactly in a “committed” relationship, so I don’t know if bringing it up would even be appropriate. I’m a bit new at having all these uncertain terms in my love life, so any advice or perspective would be greatly appreciated! — It Was Just a Jam Session

If you think you’ll see him in person soon, wait to address the issue then. If you don’t have any plans set up, send a quick text along the lines of: “Hey, just wanted you to know that when you saw me with my ex, he and I were on our way to a (strictly friendly!) jam session. Maybe you didn’t even care that you saw us together, but in case you did, I want you to know that we are just friends — we were friends before we dated — and that’s all. I like you and wouldn’t want you to have the wrong impression about my relationship with anyone else.”

My boyfriend and I have a mutual, high maintenance friend/acquaintance, “B,” whom we’ve known for about five years, but I think my boyfriend is closer to her than I am (he calls her and hangs out with her on occasion). B is nice enough, but she is too dramatic and self-centered for my personal liking. Therefore, I hang out with her pretty infrequently (2-3 times per year) and always in groups. This system works out for me quite well, but my boyfriend can’t quite figure out how to handle her and it’s getting on my nerves.

Most (90%) of their conversations (that he relays back to me) seem to be one-sided (hers) and drama-filled (issues with men, work, etc). He frequently complains to me about how B is so negative, she can never seem to get her life together, or she is never in a good mood when they talk. Just yesterday he mentioned that she recently sent him a few text messages and after he didn’t respond within 10 minutes, she frantically sent more texts trying to figure out where he was and why he didn’t respond to her quickly. He didn’t like her behavior, so he purposely didn’t respond until the next day.

All of this leads me to wonder: What type of friendship is this? Why does he continue to be friends with someone who is such a Debbie Downer in his eyes? I believe it’s because he had a dysfunctional home life where he was forced to take care of and protect his mother during some difficult times (verbal and physical abuse, drug use, and the like). His tendency to gravitate towards needy/high maintenance/damaged women has continued throughout his adulthood (his son’s mother and another ex-girlfriend were verbally abusive and manipulative). To this day, his mother still leans heavily on him both emotionally and monetarily.

Given what I know about his upbringing and difficulties with setting boundaries, especially in his relationships with women, how to I maintain my own boundary I have set with B even though my boyfriend continues do interact with her? How do I keep her drama out of my life when my boyfriend keeps dragging it back into our relationship? — Tired of the B-Shit

I would tell your boyfriend that because you find B so emotionally exhausting and because her friendship/presence in your life doesn’t bring you anything, you prefer to keep her on the fringe of your social circle and that you would appreciate it if he would respect that and quit pulling you into the very drama that you are trying to avoid. You shouldn’t tell him not to be her friend, but you can tell him you don’t want any part of the friendship he has with her (meaning you don’t want him to update you on their interactions or what’s going on in her life). If he doesn’t respect that, then it may be time for you to start setting some boundaries with HIM.

Follow along on Facebook, and Instagram.
If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.

Leave a Reply

Your email address will not be published. Required fields are marked *