AIO friend's BF wants to see me cry?

This is all just weird to me. I [23F] have a friend group [26/27sF] I've known since high school and we've all gotten way closer since they've moved back here to our hometown after being away at out-of-state colleges. They are all dating and my one friend [26F] got a boyfriend [32M] more recently. Our group has been introduced to him on a handful of occasions but I, personally, have not had a conversation longer than maybe 10 minutes that was full of small talk ( "You seen Wicked yet?" "Nah, I don't like musicals." "Thats cool. Not for everyone. But you have to admit the High School Musical Movies banged.") More to the point, we have group chats among my friends, their boyfriends, and among the boyfriends that we are all aware of. The friends who do pilates have a groupchat together, all the boyfriends have a groupchat together, the boyfriends who go fishing have a groupchat, only the boyfriends who work at the same places have a chat, etc. A different friend's boyfriend [28M] has brought it to me attention that he's been commenting some weird to some of the other guys about me, not explicitly weird I guess but enough that he's wanted to tell me the comments were being made. He's said some stuff that's like meh, like poking fun at me for being so pale or my lack of arm strength (my whole friend group works out except for me haha). He has said one comment that kinda made us all pause but it was just a one-off distasteful joke that did not land and made it clear we were not the correct audience for that humor, I chalk it up to the age difference maybe.Generally, he has allegedly been talking about how i'm too positive all the time and not everything needs a happy outcome or that i'm always happy even if theres nothing to be smiling about. Which to me is like, hello? Wtf. I feel like I don't even talk that much so i'll laugh or just active listen in groups but yeah I try to be positive. I get that it can be annoying but i'm also trying to look at the positives for my own sake and peace of mind most of the time. He has also apparently been asking if any of the guys had seen me cry before and if I cry often, saying "it'd be nice to see (my name) cry." Which, odd but idk. This has also kinda involved me being pale and him apparently asking after each gathering what a certain bruise I have might be from and if I'm okay. Tbh i don't even realize when i have bruises on my arms or legs, I just run into stuff a lot but it's really not bad. I talked to my friend who is dating him and said that I heard he was asking a few kinda weird questions about me and she just said stuff like yeah, they talk about all her friends together. Which I think is not unexpected but I asked what they've talked about concerning me. She said she's just warned him about saying things related to my scars (turbulent childhood stuff) and he's asked a few things about my personal life. This honestly only made me more nervous because, and idk if this is tmi, but i'm the only virgin in the group and i've never dated. My friends are super cool and have never made me feel weird about this despite us talking about sex related things like their kinks, turn ons, etc lol, but it is not something i'd like them to tell their boyfriends (which i've voiced). I pushed more on this and she confessed that she told him i've never had a boyfriend but nothing about me being a virgin and she said she did disclose a few elements of my childhood but nothing in detail. So, that's fine. She did say he's asked about me a lot because he wants us all to go to the beach or a waterpark sometime, so i think he might be trying to be considerate. I guess i'm posting this half way to vent but he's started showing up to our group hangouts more and he's just started saying more stuff that's overall is not crazy, I think he's just making more effort to talk to us. The guy/bf who originally brought this to my attention [28M] keeps bugging me that this new guy is weird and it's psyching me out though. I think they don't get along. I don't have guy friends except for my friends bfs who i'm not THAT close to but if one of them is telling me to be on guard how am i not going to be anxious. Now every time our group gets together I'm getting anxious to go, I know i'm probably overreacting but I need some sort of confirmation.