My friend with benefits, Penny, and I had been having a complicated on-again-off-again relationship for about three years at this point. I loved her like a friend, the sex was usually incredible, and she was fun to spend time with. However, I didn’t see myself ever wanting to marry her or have kids with her or anything of the sort. I was hitting a point in my life where I was starting to think that it might be the right thing to try to ‘settle down’ and find someone I actually wanted to be with.
I changed my OkCupid profile to one that was looking for something a little more serious and started to message women that I might be interested in. Worth mentioning, Penny and I were also on AdultFriendFinder with a couples profile — though that had stalled out significantly — and I had my own solo profile for trying to find women for something casual.