Unlike many of the characters on Community, Alan has never been shown to have a relationship with a woman. This has led some fans to believe that he is gay, which would make sense given his revolving door of one-night stands and general fucking up ways. However, the show has never said whether he is gay or not, so it’s impossible to say for sure.
In the sixth season, he starts dating one of his one-night stands, the bafflingly stupid Candy Kandi. This was shortly after his brother Charlie was settling down with a nice lady, and it seems like Alan is hoping to emulate this. However, it didn’t work out very well for him. Later on, he begins dating Lyndsey McElroy, the mother of Jake’s friend Eldridge. Eventually, she convinces him to move in with her and she shamelessly sponges him off for the rest of the show’s run.
It is also suggested that Alan may be homosexual due to his love of country music and the fact that he often wears cowboy boots. He has also been arrested for streaking with his ex-wife, Melissa, and once masturbating in a movie theater. In the twelfth episode, he is seen smoking a pipe at his house and fooling around with Zoey, who sees right through him and knows that he’s just sponging off Walden.
Despite this, he’s shown to be very happy when anyone shows him any affection. This is especially true when Walden hugs and kisses him to create a fake scene for the adoption of Herb’s baby girl, indicating that Alan does have a softer side and is capable of feelings other than rage and lust.