Is my boss actually moving into creepy territory?

[Anonymous]

I have a boss who’s really playful and sarcastic with everyone. He’s funny but has a dry answer of humor. I’m allowed to tease him about it. I was talking to another male colleague who’s name is Brian and Brian was like “you’re a lady so you don’t deal with that” and my boss was like “idk if I’d call her a lady with that mouth of hers” ( implying that I curse all the time ) and I told him to shut up lol.
I was talking about a show with a female colleague and called a guy on there hot and my boss was like “he’s not a piece of meat, Megan”. He said the same thing when I called another guy hot another time. He always jokes or plays victim that I’m mean to him and will be like “Megan told me to stop talking to her or to shut up and I just asked how her day was”
Once I told him to “f**k off” but was kinda smiling and he said “I’m glad you think that’ll make me stop”.
I kinda roll my eyes when he asks how my day is going and he’s like “I just saw you look up and roll your eyes just now” or”there you go with your eyes again”
Once he said something and eventually in the convo I was like “you know what, Nick ( his name )? You’re obsessed with me” and everyone in the room laughed and he got quiet which is unlike him lol.
I jokingly told Brian the other colleague that I was so happy and he asked why and I was like “because I have a new man in my life”. My boss was nearby and he heard this and usually butts into the conversations and got really quiet. Brian then turned to Nick, my boss, and was like “did you hear her say that?” And he kinda quietly and awkwardly was like “yeah I was waiting on you to say something”. I then said I didn’t have a boyfriend yet and that I would tell Brian when I had a new boyfriend and Brian was like would you tell Nick?” and my boss was like “yeah, would you tell me?”
Our workplace got renovated so my boss and I sit further from each other and he sometimes still teases me about how I’m “mean” to him lol. Is he crossing boundaries?

[Anonymous]

How is he crossing boundaries if you told him to fuck off playful. I think he thinks you’re just cool, easy to get along w. You’re a rare find. Men can’t be the way they are w their boys when they’re sound women. There’s always a chance of being accused of something. It I think to him he can talk like that w out fear of getting in trouble. Which you reinforced by telling him to fuck off. So I’m lot sure what you’re referring to as far as asking if he’s crossing boundaries.

[spartan55]

You tell him to fuck off and are wondering if he is 'crossing boundaries'? Really? What are your boundaries? Is everyone in the office familiar with them?