Have you ever seen someone on Fetlife and been like “I think that would be a good person to get to know, play with, and possibly explore a relationship with”? Of course you have. And if you’re the average dude on Fetlife, you’ve immediately messaged them. If that works for you, great; I hope you get everything you want out of the interaction.

But in my case, I play the longest game.

There’s someone new-ish on Fetlife who I think would be a good fit for my needs — she’s close to my age, we share similar interests, and she seems intelligent (smart girls are sexy). The thing is, she’s new, and I don’t want to get lost in the avalanche of PMs I’m sure she’s gotten. Plus, I don’t want her to feel like I’m trying to prey on her. I followed her, but didn’t try to friend her, and I haven’t interacted with any of her content yet except for maybe hearting a status update once.

In my head I’m building out all these scenarios where I message her, we hit it off, we go to dinner or on a coffee date, and everything goes better than expected. (Well, I don’t do it often, because I’ve had a lot on my mind lately, but sometimes when I see her name that’s what goes through my head.) The key phrase is “in my head”, though. I have yet to reach out to her.

And I don’t know when I will.

When’s the right time? When is she “not new” enough? When would my message break through the chatter and noise?

That’s the problem with the longest game: I never win or lose, because I’m not actually playing. If I don’t approach her, I can’t get rejected, and rejection is a major issue for me — I accept that women have every right to reject me, but I was rejected a lot as a teenager and in both of my marriages, and I don’t like that feeling. So I try to avoid it. It’s similar to how, even when I know someone and know they want to play with me, I still don’t ask them to play because what if they say no this time?

I’ve been active in the kink world for a very long time and I still have these worries. Which is why the longest game and I are good friends.

Maybe someday I’ll change that. Maybe.