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Dan Sheehan
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This one gets lost in the shuffle a lot because it was so late but it was a perfect encapsulation of everything the show did well. Male friendship, great guest starts, humor, and then a devastatingly well soundtracked closing

I didn't take it as Gretchen "dealing with" a boner as much as she was trying to comfort him in a way that didn't involve acknowledging his emotions about the situation. It shows that, as far as their relationship has come, they still have a lot of ground to cover. Gretchen has stated multiple times in the show's run

Oh man that final exchange is brutal

"Aint that just the way" from Over the Garden Wall