Is it weird for a guy to talk about other women (including teachers)?

So, I’m in a bit of a pickle as I like my coworker. Hes a sweetheart but I’m questioning his behavior after today.

One time, we had training together and I mentioned an old teacher we both had. He proceeded to say “Honestly, Mrs.Smith is such a milf. And you know who else? Mrs.Jones. Oh and Ms.Bates but before she got pregnant and had her kid.”

His face then fell (probably upon seeing my surprised expression) and he sternly said “Don’t repeat that to anyone.” I would assume this is more so bc I’m friends with his best friend’s girlfriend, but looking back at it, it felt kind of weird.

I bring this to attention today because we were at work and out of nowhere, he asks if I knew a girl. I asked if she was related to a guy in my grade based on the last name and he confirmed. I joked if she was better or worse (in regards to behavior cus the dudes a pothead) and he said “Well, let’s just say shes really hot,,,,” I thought?? He was referring to the guy’s YOUNGER sister???? (Im 17, hes 18, and if this sister is younger im thinking a few years under me)

So my jaw dropped and he didn’t continue, rather went over to our other coworker who he’s close friends with and asked him if he knew the same girl. I’ll have to double check but I’m very,,,,off guard

I was told this just shows he trusts me if hes saying all this to me, which would be good, but it feels more weird + more of something you’d just say to your guy friends, which I think would not be good for my case?

So yeah uh...is this? Weird? He’s never had a girlfriend before so I don’t know if this is just him being awkward or something else? Maybe I’m just one of the guys? Or maybe the whole thing is strange,,,

Submitted November 14, 2019 at 11:59PM

So, I’m in a bit of a pickle as I like my coworker. Hes a sweetheart but I’m questioning his behavior after today.One time, we had training together and I mentioned an old teacher we both had. He proceeded to say “Honestly, Mrs.Smith is such a milf. And you know who else? Mrs.Jones. Oh and Ms.Bates but before she got pregnant and had her kid.”His face then fell (probably upon seeing my surprised expression) and he sternly said “Don’t repeat that to anyone.” I would assume this is more so bc I’m friends with his best friend’s girlfriend, but looking back at it, it felt kind of weird.I bring this to attention today because we were at work and out of nowhere, he asks if I knew a girl. I asked if she was related to a guy in my grade based on the last name and he confirmed. I joked if she was better or worse (in regards to behavior cus the dudes a pothead) and he said “Well, let’s just say shes really hot,,,,” I thought?? He was referring to the guy’s YOUNGER sister???? (Im 17, hes 18, and if this sister is younger im thinking a few years under me)So my jaw dropped and he didn’t continue, rather went over to our other coworker who he’s close friends with and asked him if he knew the same girl. I’ll have to double check but I’m very,,,,off guardI was told this just shows he trusts me if hes saying all this to me, which would be good, but it feels more weird + more of something you’d just say to your guy friends, which I think would not be good for my case?So yeah uh...is this? Weird? He’s never had a girlfriend before so I don’t know if this is just him being awkward or something else? Maybe I’m just one of the guys? Or maybe the whole thing is strange,,,