For whatever it's worth, here are my votes:
(1) He's dealing with some amount of depression and is/was taking meds to help with it. He ran out of his prescription and hasn't been able to refill it for insurance reasons. Last night he showed me a huge bottle Trazodone that his friend gave him and he intends on starting up with. It's not been prescribed to him. He said he's only recently started self-medicating.
YELLOW flag I f he has no history with pill abuse. If he has a history of abusing prescriptions, then it's a RED.
•(2) I have weak, thinning hair that breaks off quite often. It's a source of pain for me and I'm trying to come to terms with it. I've shared this insecurity with him. One evening he was rolling a cigarette and a piece of my hair somehow ended up inside of the paper while he was rolling it. He pulled it out and said, "You're fucking hair is everywhere!" He seemed annoyed and I felt really bad about it since there's no way for me to control it short of shaving my head.
ORANGE. Not abusive behavior, but still nasty and it was said with hostility. Not good.
•(3) We were trying to watch a movie on his laptop and it kept freezing. He got irritated and slammed the keyboard with his fist. This happened twice. I've never been in a physically abusive relationship, but I know it usually starts with taking anger out on material things. Again, I might just be overly sensitive, but he also mentioned he's hot-headed and can have a real temper. I haven't seen signs of this beyond this keyboard incident.
RED FLAG.
•(4) We have very different ways of spending our free time. While I've put in effort to learn about and enjoy his hobbies, he hasn't really done the same. For example, he wanted to go hiking and I haven't been on a real hike in over a decade. I gladly went and while I had trouble keeping up with him and thought I was going to vomit several times, I really tried to enjoy it. I didn't complain or ask to leave and ended up having a good time. On my end, I tried to show him this incredibly creepy video game I found and really liked, but he refused to take the controls and just sat there while I tried to show him what was so creepy and fun about it to me. His response was that it wasn't that scary and that was that. I understand not liking video games, but I guess it just feels lopsided to me and makes me feel lame for having interests he likely thinks are dumb. Compatibility issue, I guess.
ORANGE. Not just compatibility issue, but also a respect and attitude issue.
•(5) He's currently studying plants for his PhD and is just incredibly into plants like you wouldn't believe. I'm not a big plant person, but I admire his passion and take almost every opportunity to ask him about certain species, send him photos of beautiful flowers that I see while out, and only wish I knew more so I could engage with him even further on the topic. I read about plants on the bus. I subscribed to subreddits about plants. On the flip side, I'm working on my MFA in creative writing. He never asks about what I'm working on. I've tried to share, unsolicited, but he just sort of nods and there's no engagement whatsoever. Once I couldn't sleep because I'd come up with this terrific (I thought) idea for a collection of short stories. I was so excited. I tried to tell him about my idea the next day and he stopped me in the middle, saying I shouldn't talk about my writing plans because then I probably won't write. Another compatibility issue?
YELLOW flag. I'm not too sure though without hearing him say it.
•(6) He seems to hate his life and is bitter/complains about almost everything: the bus, money, his apartment, his car, his PhD program, the quality of his coffee. I'm afraid I'm next to be complained about. He used to apologize for complaining, now it just seems a more natural state. This is hard for me because I'm fairly optimistic and feel a little dragged down. Not sure this is a flag.
RED flag for me personally. Some people can live with this though....I just don't like being around people who bring me down. I'd rather be with people who bring me UP.
•(7) While we hang out with his friends, he virtually ignores me. It doesn't seem to be intentional, just that he's more interested in talking to other people. I often feel like I'm fighting to be heard from the corner in these situations and it's disheartening. His friends take only a vague interest in me and while I ask them questions and try to engage, they just sort of answer and then turn away. It makes me feel more like some kind of uninteresting material accessory to the guy I'm dating, rather than a person. He doesn't try to help me integrate. I have minor social anxiety (which he knows), so that helps in making it incredibly unpleasant for me.
ORANGE flag. Again, not abusive, but very disrespectful. And his friends are probably only going to show you as much respect as he shows you.
•(8) He's almost always late and I'm almost always waiting. I feel like he doesn't respect my time and that's translated into me not respecting my time (if that makes sense). When he says he'll be at my place at 6pm, I make sure to stop what I'm doing, come home, take a shower, change, whatever I need to do, so I can be ready at 6pm. Usually there's a 1-2 hour wait after that. I've come to just put those 1-2 hours in this gray area in my head where I can't start doing anything because he might actually be on time or only be 30 minutes late.
ORANGE flag.
•(9) My grandma has breast cancer again. I told him this and that she was going in for surgery and all he said was "sorry". It hasn't come up again. This is probably normal for a 2.5 month relationship, though, right? If he's not fully invested in me, why should he be invested in my grandma, I guess?
ORANGE flag. I don't care if I've only been dating someone a week, I'll at least check in with them to see if they're feeling okay about it. If he's not a "talk about feelings" kind of guy, he still could have asked you how you were dealing with it and let you talk if felt so inclined.
•(10) He gets really jealous. He doesn't like the fact that I have guy friends and doesn't think there's such thing as a platonic relationship, that at least one person is always interested in the other. Still, he tolerates the fact that I have guy friends and hasn't asked me to stop being friends with anyone. On the subject of friends, he met one of my few girl friends and later told me that he thought she was "cantankerous". I've never once said anything negative about any of his friends.
RED FLAG. Huge red flag. He's not asking you to stop hanging out with them yet. Just you wait.
•(11) We only watch the movies and listen to the music that he wants to watch/listen to. This is confusing because he'll almost always ask me what I want to watch or listen to, which makes me feel good, but then he'll go on to shoot down my suggestions and we end up with whatever media he prefers anyway. I've basically given up on this.
YELLOWISH-ORANGE flag. He could just be the type of person who is set in his ways and needs to be reminded that your preferences are just a valid as his. However, if it happens all the time and doesn't change after you talk about it, upgrade that to RED.