I admire Dean for being realistic. I wish I'd been that realistic at 17. Kind of a non-supernatural, non-terminal version of the decision a guy made about his relationship in season 3 of a previous show of yours.
Universities (i.e. colleges) are businesses: they want students who have career prospects so they can look good for facilitating them. Blanket love of academia, such as I had at Rory's age, is not likely to convince them. I got into 4 of the 6 I applied to, but I'd have preferred in retrospect to have treated it as a stepping stone to a career rather than as a fun thing to do after high school. (Sidenote: the one I went to is struggling as a business now.)
The Jam is the band Paul Weller was in.