Middle aged men still making lame sexual jokes

I’ve been texting an old friend every once in a while to laugh over our dating tribulations. Nothing serious, we haven’t seen each other in years. However, I have been sharing the more gross things that guys have said to me on the apps and lamenting on how frequently some rando will just shoot their shot in the most grotesque way, which is about every other day. I have a very tame profile and yet…

Anyway, today, we texted and he made a joke that included mention of a sex toy. I told him to stop being gross, he sort of laughed, and I told him to stop being a creep. I think he got mad because he responded in a rude way.

His joke was something I would have laughed at when we were in our 20s…but we are in our 40s. Grow up. On top of that, my OLD experience has been pretty negative. More than half the guys I talk to get creepy (and, no, I’m not just talking to one type or one age range). I’ve told him that I feel hounded by men all the time and feel treated like a prostitute.

I think I’m being sensitive but not hyper sensitive nor over sensitive. While I don’t actually think he was trying to be sexual with me, and he was just using poor judgment, I don’t think I need to interact with someone who doesn’t care if they made me uncomfortable. It’s similar to the guy who mentioned how he wanted to have an OF account (as a joke in our first conversation) and then claimed he wasn’t being sexual. Most men have no concept of how bad it can be for women on OLD. I talked about it with my ex who agrees that it was weird (my ex and I were together for a decade and I never witnessed creep behavior). Additionally, my best guy friend who I’ve known for decades has never made jokes like that. We’ve chatted about sex, but not in the same context (not in a flirtatious way), and he would be horrified if I told him his words made me uncomfortable.

I’m really disappointed in my other friend and can’t wrap my head around behavior like this. The initial joke and the doubling down when it didn’t land.