Dear Dr. NerdLove:
I’m a gay man. In my tennis group there is a 32 year old guy that I find very attractive, who I have known for about 3 years. We were never close friends, but rather just friendly acquaintances.
About 6 months ago, out of the blue, he started sending me direct messages, such as “good morning”, “how’s your day going”, “good night”- daily, several times a day. The conversations were short, but consistent. On several occasions I would lightly flirt with him. He would thank me, but he would never flirt back. So I assumed he was not interested in me beyond just being friends.
After a few weeks of receiving his daily text messages and me hoping for more, I finally flat out asked him if he would go out on a date with me. He politely turned me down. I was disappointed, but also relieved to at least have a concrete answer. In this same conversation, I apologized for flirting with him thinking that it probably had made him uncomfortable. He said, “no, I definitely hope that doesn’t stop”
Knowing that he was not interested in me but that he enjoyed my light flirty comments (by light, I mean a level 2 out of 10), I felt the freedom to increase the flirting level to a 5 out of 10. So now, instead of just complimenting him physically, I added a sexual desire component without being raunchy. This continued for a few more weeks. Still the flirting was one way traffic.
Then, one day, he flirts back! And not only that, but he escalates it by sending me a half nude picture! It caught me so by surprise that I started shaking with excitement. I told him that I was confused, that I didn’t think he was interested in me in “that way.” He said that he was attracted to me, but that he has a “policy” of not dating anyone from the tennis group.
Since then, for the past two months, the flirting is now two-ways and has progressed to video-cam sex twice a week… Our sexual interaction is exclusively virtual. When we see each other in person on the tennis courts, we’re just friends. No one in our group knows we have this virtual side thing going. He keeps saying that “soon” we will have actual sex. However his reasons are pretty flimsy as to why it hasn’t happened yet, so I assume he probably just doesn’t want to take it to that level. Yet every time I think we have reached the limit of how far this is going to go, he eventually pushes it to the next level. It’s just been such a f…n long, slow process… Ugh!
Is he just playing control games? Or is he the type of person that just takes a long time to develop a relationship? Seems that every time I try to define the relationship, I get turned down, but yet things do seem to be progressing, which leaves me confused because I want a “normal” relationship – and this feels more like a game, which granted I have been a willing participant.
Meanwhile, I keep meeting other people on dating apps, hoping to find someone that wants to date me as much as I want to date them. But no luck yet.
Do I do nothing and continue allowing him to dictate the pace and depth of the relationship? Or is there a level of toxicity already that makes it hopeless to expect it to ever be healthy and I should instead just end this now? Or is there a compromise solution that you see?
Ready Player Two