Oh, brother, that is a rough hand indeed. I am remembering a prayer that I didn't understand when I heard it first:
Lord, my heart is broken. I never want it to mend.
I'm really in no position to give you advice, and yet here you are, so I'll give it a shot.
I wonder if going to medical school is the right thing if it's not your personal ambition. If it isn't, then I wonder if you will see it through, and then stick with the career afterwards. It's a grueling, expensive path to choose if it's not really for you.
I wonder if you really want to be a "player". Most of the game industry is marketing hype, and - having tried it - I personally don't think that "being a PUA" is a healthy identity, especially when it revolves around nightlife. I'm not criticizing men who enjoy that, it's just not how I want to live.
Rather, I see it as being about developing my social skills generally, having the confidence & experience to strike up a flirtatious conversation when the opportunity arises, plus some basic logistics&tactics around getting numbers and moving the interaction forward from date to date to my/her place.
"I like to think I'm a good person with morals, and it seems a lot of people here say one needs to be a bit of an asshole to get laid."
Sure, that works with certain girls, but I would say that it's better described as not caring much about being agreeable. Think of a good father with his daughter. He isn't an arsehole to her, but he isn't trying to win her approval by being nice either. He mostly leads their interactions, and will firmly say no when it's appropriate. If she tries to control him with emotional manipulation, he laughs and teases her for being a bossy boots. I think that's the general vibe that good game preaches. Look at videos of Mystery infield, he's affable as anything, nothing arseholey about him, and of course his famous neg is about disqualifying yourself as a suitor in order to give her room to chase your approval, rather than being a dick in order to lower her self esteem and make her vulnerable, as it is always presented by the MSM.
You can write your own meaning from your situation and the things that you feel insecure about. Just as an example:
"I don't drink or smoke either, so I'll feel out of place at parties."
Could become:
"I don't drink or smoke either, so I'll attract positive attention at parties. High value girls will find it attractive that I respect my body, people who want to improve themselves will see me as a role model, and while I'm friendly to everyone who shows me basic courtesy, I choose not to be friends with people who are committed to intoxicating themselves anyway."
"I am horrible with women and as soon as I talk they tend to get annoyed."
could become
"I am learning more every day about how to put my best foot forward with women, and I'm good at picking up on feedback. Besides, I ultimately can't know why a girl I've never met before is annoyed, but I'll choose to guess that it's because she's with a less handsome guy than me and wishes she could upgrade to this here CK model."
I'd like to give special attention to this one:
"Now I get intimidated, especially by attractive women."
First, that's totally normal for the typical guy who doesn't spend their day surrounded by models. A good way to get more exposure and change that is to go to shops with attractive women working there, who are paid to be nice to you and answer your questions, and talk to them about mundane stuff to do with their shop's products and other small talk. Pretend that you are buying gifts for a woman if necessary. Try to do this for an hour a day for at least month.
Second, it's probable that you have a "highway to terrible" in your brain. As far as your subconscious knows from your life experience so far, 100% of the time you begin a romantic interaction with an attractive women, it leads to her death, the collapse of your life's vision, and years of pain.
So, I might change it to something like
"Now I know the urgency of life, I am sometimes daunted by the challenge of being fully present, especially with attractive women. I don't want to go through the pain of the woman I love dying before me, and I also know for a certain fact that I am capable of carrying that and loving life even more, warts and all. Indeed, the fact that I am already carrying this gives me a true depth and resilience that is outside the experience of almost all the women I meet, not to mention the boys hitting on them. If they knew my secret, they would be ten times more daunted than I ever am."
I do recommend that you keep this a secret from people you interact with regularly in your daily life, by the way, especially at college, and with the women you grow close to, especially in a relationship's early going. I do not mean that you should not practice the art of grief for the rest of your days, only that this story belongs to the sanctum of your heart and your true friends and family, not campus gossipers and girls you barely know.
I've watched this film a few times now, after someone close to me has died. I find it cathartic. I hope it does the same for you.
https://www.nfb.ca/film/griefwalker/
I you agree, I will pray to our Creator to take away your fears, so that you may see more clearly how best to serve the life that He entrusted to you.