Blaine Anderson/Season Two
 Season Two
When Kurt Hummel tours the school of the Dalton Academy Warblers in Never Been Kissed, he encounters an overwhelming performance made by Blaine and the other Warblers whom were singing Teenage Dream by Katy Perry. Blaine informs Kurt that Dalton Academy has a zero-tolerance rule on bullying and that the school is not an all gay school, though Blaine is gay himself. Kurt breaks down in tears because of his troubles with being gay, and Blaine and him exchange phone numbers. Blaine's interference with Kurt's life is a positive one and increasingly grows warmer as the season progresses, playing a key role in Kurt's transfer to Dalton Academy.
Their rising relationship can be seen in the episode Baby, It's Cold Outside when Blaine tells Kurt that he's much better than any female partner. Blaine's feelings for Kurt aren't as romantic as Kurt's are for him, yet.
Blaine confesses his love for "this boy" to Kurt Hummel while they get coffee. As it's Valentine's Day, Blaine wants to serenade his lover with song, and he asks Kurt if it's too corny. Kurt blushes, thinking the crush may be him, and tells him that the plan sounds perfect. At Dalton Academy, Blaine holds a mandatory meeting and asks the Warblers if they'll help him serenade his love. The catch is that he wants to do it off campus, which hasn't been done since the creation of Dalton Academy. The group immediately rejects the idea, but Kurt persuades them, saying it'll help their singing at Sectionals.
When Blaine sings to his love at his work, Gap, he tells Blaine off, hating the scene Blaine made; he has not yet come out of the closest and is disgusted at what Blaine did.
Blaine is seen as the main vocal for Dalton Academy, and he offers Kurt the oppurtunity to sing in his stead. Kurt sings Blackbird, a song that moves Blaine. Later, when they're both alone, Blaine shares how Kurt moved him, telling him that he's been looking for him forever. Blaine leans in and the two have their first kiss.