Just a Poor Shlub
Lester is kind of a complicated dude, and he goes through some big changes throughout the movie. When we first meet him, he seems pretty pathetic and beaten down by life:
LESTER: Both my wife and daughter think I'm this gigantic loser, and they're right.
His wife and daughter don't really seem to like him, he gets zero respect at work (where he might also be getting fired shortly), and his greatest daily pleasure (according to him) is masturbating in the shower every morning.
Basically, he's feeling miserable and impotent, and movie does a pretty good job of making us feel sorry for him.
Or a Raunchy Pervert?
However, Lester's life takes a sharp turn when he sees his daughter's friend, Angela, perform a dance/cheer routine at a school basketball game. Even though she's his daughter's friend and super underaged (and he's married and all that), he becomes immediately infatuated and starts fantasizing about her.
Totally gross, for sure—on a few fronts—but his new fantasy life seems to wake him up from the haze he was living in personally and professionally, and it inspires him to change things up:
LESTER: It's the weirdest thing. I feel like I've been in a coma for about twenty years, and I'm just now waking up.
He starts exercising, smoking weed with the teen boy living next door (who becomes Jane's boyfriend), and standing up to the people around him who had previously written him off—including his wife, Jane, and his employer.
Sure, smoking pot with someone else's kid and exercising so he can look good for his fantasy teen lover are sketchy things to do… but if we can just set that over to the side for a moment, we see that it is good that Lester has realized he doesn't have to settle for being miserable.
You see, prior to his close encounter of the pervy kind with Angela, Lester seemed to kind of think that his life was over now that he was middle-aged and he had to just settle for the hand he'd been dealt—but his feelings for Angela snap him out of that, reminding him of what passion feels like.
Reawakening at a Price
Lester's 180-degree turn comes at a huge cost, though—his life. His friendship with Ricky catches the attention of Ricky's father, Frank, who misinterprets the Ricky/Lester situation as sexual. He goes to confront Lester and, much to our surprise, we learn that it's actually Ricky's dad who's harboring a man crush. Thinking that Lester is gay, Frank tries to kiss him… and then, after being rejected, decides to kill him.
Because that's what you do when you're rejected, right? (Wrong. So wrong. You listen to Adele and eat ice cream.)
Of course, we'll talk more about Frank Fitts in his character summary, but it's interesting to note that he and Lester are actually kind of similar—in that they both know how what it's like to have to ignore or deny your passions for years and years on end.
So Much for My Happy Ending?
As Lester himself says, we could feel pretty crummy about what happens to him. After all, he's deader than a doornail.
But the movie doesn't really invite that—if anything, the story seems to end on a happy note, with Lester recovering from the more immature aspects of his reawakening and finding actual happiness and satisfaction.
First of all, he backs off from his pursuit of Angela, realizing that it was completely inappropriate. Then, in his final moments (yes, his life flashes before his eyes), we see that he is focused (mostly) more on simple moments and small joys than the feelings of lust that touched off his whole renewal.
He's overwhelmed by the beauty of life and seems grateful that he got to participate in it. Considering how his particular story ended, that kind of contentment is pretty miraculous, if you ask us.