Blaine initially served as a mentor for New Directions member. They meet in the Season Two episode Never Been Kissed, when Kurt attempts to spy on the Warblers, and immediately become friends. They begin dating in Original Song, after Blaine kisses Kurt, forming the first male- male couple on Glee.Feb 03, · Glee - EVERY KISS EVER ( Season 1) - Duration:. Well, touching, I suppose, mainly because of the performances by Colfer and. Blaine Devon Anderson is a fictional character from the American musical comedy- drama television series Glee. Exes Kiss For The First Time Since Their Breakup. Top 10 Unforgettable Kurt & Blaine Moments on Glee - Duration: 9: 21. March 15th is the air date of the episode that Blaine first kissed Kurt. Season 2: Episode 6: Never Been Kissed: Kurt and Blaine Meet. Season 2: Episode 9: Special Education: Kurt transfers to Dalton Academy Season 2: Episode 12: Silly Love Songs: Kurt confesses his feelings to Blaine after Blaine embarrasses himself trying to woo another guy, unsuccessfully. Mar 16, · After a long buildup, Kurt ( Chris Colfer) finally got his first consensual gay kiss on " Glee" last night, and it was.