The night before Kurt enrolled in Glee club, in his sophomore year, he enters in a parallel world where he is a girl and has relationships (to platonic to more physique) with several boys that she may or may not know, like the quarterback Finn Hudson (whose he later fall for), the linemen Puckerman, the two other footballer player Mike Chang and Matt Rutherford and the invalid Artie Abrams. (+Jess St. James) And the following day through the rest of the year, he spent with them, knowing that he could never be that close (or flirt with) to them as he did as SHE.

For three other years, he passes the same event just on the day to finding back the Glee club.

The next year, in junior, David Karofsky was also on his- no, her harem, with the addition of the new guy Sam Evans and a ton of warblers.

On his last year of high school, in senior, she flirt and may have affair with Sabastian Smyth (since he and she is in relationship with Blaine), got Rory Flannagan and Joe Hart fawning for her and this cute future NYU boy Chandler Kiehl.

For the last world warp, Kurt (as in Courtney) meets Hunter Clarington even though she has no reason to since she breaks up with Blaine (for no apparent reason), Adam Crawford and Elliot Gilbert.

All in all, he just notices that everytime he got a boy as a girl and once he met them as boy, the encounter is indefinitely better in the first case. Being a guy liking guys sure suck but he won't change that, being proud of who he is.