<human>: I'm a college student in my first serious relationship .I've been with my SO for a year. 

He's the first person I've ever more than kissed and I've only dated one person before this. I'm 21 but I feel like I have less relationship experience then the average teenager. Even though we've been together for a year I still don't know how to comfort my SO in the way that he needs . 

He's going through a difficult time right now. His mother has cancer, a close relative of his recently passed away, and his family is in a tough spot financially. He just found out he is under academic review at our school. Like the moron I am I didn't check my phone yesterday until midnight to see that he sent six messages saying he was under review and needed someone to talk to (I tried calling him but he was asleep) 

I think I'm really, really bad at this guys. Whenever I try to say something at all reassuring I sound like a awkward robot. A year ago I couldn't even hug properly, because I probably gave on average one hug a year. I've had a pretty easy life and I'm never sure what to say or how to relate to people when they confide in me about very serious challenges they face. 

I'm the type of person who holes up by themselves when they feel down . Again, I've had little go wrong for me but i've never felt catharsis venting or confiding in anyone about my problems. All my friendships have always been more about hanging out and shooting the shit then emotional support . 

How do I become a more supportive partner for my SO in general? Also anyone whose ever been in similar circumstances as my BF how can I best support him/cheer him up right now?

Provide a brief overview of the text.
<bot>: emotional support doesn't come naturally to me, how can I support my bf at a very difficult time for him