- “Glenn – Irish studies suck, German studies suck, everything here sucks, sucks, sucks, sucks, sucks!
Rory – That yoga's really working for you, Glenn”
- —A day in the life of Glenn[src]
Glenn is seen as a very nervous, geeky, social awkward and flustered person. He is first seen in an episode of Rory and Paris Geller's first party at Yale when he is trying to carry a keg up the stairs of the dorm and hopes someone will help him.
He was alongside Rory and Paris trying to join the Yale Daily News. They have to make a newspaper hat and Glenn is very nervous and unable to make one.
Rory and Paris end up accompanying Janet and Glenn to Florida for freshman year Spring Break. While Glenn has a crush on Janet, she is only traveling with him because her friends went down without her. Paris forces Glenn to let her drive his mother's minivan because Paris feels "if I'm going to die, it's going to be by my own hands." Later in the episode, Rory and Paris find him drunk and running out of the ocean with his bathing suit on in the middle of the night.
While everyone is packing up at the end of freshman year, Glenn tells Rory that he is getting back together with his girlfriend from back home. He shows Rory a picture, however she gets freaked out when it is a picture of a young girl ("Glenn, this girl is like 12 years old!"). Glenn responds: "It's a picture of her when she was younger. Don't turn this into something dirty; she drives and everything!"
When Rory gets back into being involved with school and the school newspaper, she along with Doyle McMaster, get jealous of the fact that one of Glenn's stories from the previous year got picked up by the New York Times. It makes Rory feel guilty about spending the whole summer traveling around Europe with her grandmother instead of working on her craft.
- Glenn – Every time you talk I hear my mother. And see my mother –
- Doyle – Stop comparing me to your mother!
- Glenn – Stop acting like her!
- Rory – You're seeming particularly sassy today, Glenn
- Glenn – I know, must be my new glasses prescription
- – A most unusually chipper Glenn