I want to go to see a doctor and talk about it but I fear I'll look dumb/not have anything bad enough to warrant a doctors visit
I just overthink things a lot and I will run a situation through my head till I am the bad guy no matter what. Especially with friends and family not so much with strangers.
I dropped out of college because I wasn't attending classes because before class I would convince myself that i would burden someone or get called out in front of the class or something dumb like that 
Whenever I do work for someone I find it hard asking them for payment. I can't send an invoice without letting them no it's not in a hurry 20 times over.
If I'm texting with anyone more than 3 years over my age I'll retype it 100 times.
I don't like asking people to do something because I fear they'll feel forced to or not be able to say no.
Worst of all if I get invited to something I'll convince myself they are hoping I say no and end up being as hermit.
I have trouble expressing my relationship concerns with my gf of 4+ years because I feel like I would be controlling if I did.
I also have trouble asking for help. With anything. Money, unloading my vehicle, school or work. And mental health ig

I wasn't always like this. I was very outgoing and smart in high school and now I feel like I don't know anything and can't talk to people. Would the death of a parent "trigger" this? And if it could be caused by the death, should I not seek medication?

Also what are my biggest concerns about medication? If needed at all.

TL;DR OP lists his symptoms like he is on WebMD when he should probably not