Matt's need to fit in the "norm" is what essentially destroys his friendship with Lillian. It leads to a forceful situation none of them wanted (or maybe Matt did want something romantic with Lillian, but it certainly didn't need to go that far if he had listened to himself rather than social pressure).
It would have been interesting to delve deeper into his childhood and past, to see what pushes him to insist and force himself into boxes and categories he thinks are "right". (to the point of forcing others into boxes as well, and hurt them in the process)
Maybe that's why he goes to Jo's bar so much, so that other people force him into boxes against his will, as a sort of unconscious punishment.
ALL RIGHT that's gonna be it for psycho-analyzing my own characters :D see you tomorrow!
--> This is a rerun of the finished webcomic Go Get a Roomie! You can find these two strips in the old archive >here<!