He thinks the day she got on that plane and left him with a ring box in the snow might be the worst day of his life. That says a lot when he thinks of all the bad days he had Sophmore year before Regionals. He knows the proposal was crazy, it was his last ditch effort to keep her from pulling away completely and it backfired. He doesn't know who he is without her. He wouldn't have even gotten into college without her pushing him everyday and losing her isn't anything like losing Quinn. He's lost his anchor.
He doesn't know what he wants to be when he grows up, but he knows he needs to decide soon. He wishes he could talk to her and ask her opinion, but he hasn't been able to since she walked away. He spends his time in gen ed classes and hanging out with Puck and Mike, but they have girlfriends and he's always a third wheel. He stops going out with them, only attending one party when Quinn begged him because Puck couldn't make it. He sees her taking pictures and tries to look happy, but everything reminds him how much he misses Rachel. At the end of the school year he's still miserable, but he's made the Dean's List and his advisor has been steering him towards the education path and he thinks being a teacher might be alright.
He knows she'll be at the end of summer party, he asked Tina to text her. Tina told him she would, if he promised not to make a fool of himself. He had to step away when she walked into the party, but he thinks he kept his promise in the end. He'll wait to text her though, because he doesn't want to scare her away, and he doesn't really know what to say. He's not sure he can just be friends.
School starts up a few weeks later, he's back in on campus in an apartment with Mike and Puck and Tina too, but on paper she lives in a dorm. Quinn isn't happy that Puck wouldn't move out with her and he's there a few weeks later when she stops by to pick up her things. He helps her carry the box to the car and in the moonlight, they are both struck by the thought of what might have been.
"Could you ever..." she starts and then stops, because they both know it would never work. And when he hugs her goodbye, it's for the last time.
Right before Winter break, he declares his education major and thinks maybe teaching history to middle schoolers could be pretty cool. He knows its the right choice when his advisor hands him a packet for a program that will repay his schooling if he spends 4 years teaching in an inner city school. He lists each of the borroughs of NYC as his top choices, but doesn't tell anyone.
He's been texting Rachel a little, about a movie she mentioned seeing on her Facebook page and the play she's rehearsing for where she's playing the second biggest female part. She sends him pictures of things in the city and they never talk about anything serious. She won't be home for break and he thinks that's ok, because he's not ready to tell her his plans yet. He needs to stay focused too.
He spends Christmas at home with his mom and Burt. They meet Kurt's boyfriend and as they try and dazzle everyone with their exciting California life, he keeps his secret safe and trys to convince everyone he's moved on.
At midnight, Rachel texts him a picture of Times Square and says "wish you were here." He wants to text back "me too" but just sends back "Happy New Years" and goes to sleep content for the first time in a long time.