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He's a war veteran with a scar from a German's rifle. He had a deadbeat dad and a just plain dead mother. He worked his way through school. Joined the army. Studied law. And was voted Man of the Year by the Kiwanis Club (3.41).
And like Rodney Dangerfield, he can't get no respect.
His main detractor is Jean Louise's Aunt Alexandra, a woman much more obsessed with status than accomplishments. Not surprising, since status requires no work whatsoever—you're born into it—and accomplishments (she has none, btw) require blood, sweat, and tears. Alexandra completely ignores Henry's veteran status and his education to focus on his comparative trashiness:
"He licks his fingers after eating cake. He coughs without covering his mouth. He picks his nose. He got a girl "in trouble" at University." (3.73)
But Aunt Alexandra thinks he's an opportunist, "grabbing everything Atticus has" (3.75), including his daughter. And she says, "Fine a boy as he is, the trash won't wash out of him" (3.72). Translation: Henry perfectly illustrates the issues with social class that are present in Maycomb in the 1950s.
Jean Louise fights Alexandra, but we're not sure she actually thinks differently. After all, Jean Louise would fight Alexandra if she said the sky was blue. But the way Jean Louise treats Henry make us think she agrees with Alexandra. She doubts Henry's war story, and she often teases him cruelly and laughs at the guy. Maybe she doesn't realize how mean she is? At one point, she apologizes to him, saying "I swear to God I've never laughed at you, Hank" (5.256).
In that moment, we're inclined to believe her.
The love affair doesn't last. Henry desperately wants to marry Jean Louise, and he believes he now has the social status to do it. But Jean Louise is too independent (or hard-headed, depending on your view) to be tied down.
She gets a convenient out when she sees Henry at the same Citizens' Council as Atticus, and she confronts Henry for his hypocrisy. We never see Henry spout the same racist tripe that Atticus does, yet Jean Louise is much more violent in her outbursts with Henry than with her father. Why is that? Because she cares for Henry so much? Or because she never did?
Henry calls Jean Louise out on her entitlement:
"Jean Louise, I've had to scratch since I was a kid for the things you and Jem took for granted. I've never had some of the things you take for granted and I never will. All I have to fall back on is myself." (16.58)
He has a point.
He works hard but constantly finds himself on a slippery slope. Jean Louise, who often describes herself as racially blind, is also blind to her own entitlement. She insults Henry's masculinity, which pushes him right over the (metaphorical) precipice back into the (metaphorical) trashcan where he came from.
We can't understand what Henry sees in Jean Louise after this, but we see them still make a date. Maybe Henry only wants to marry Jean Louise because he sees it as his duty, like attending the Maycomb Citizens' Council. Maybe he has to do it, even if he doesn't want to, in order to fit in. For upper-class Jean Louise, the ability to freely follow her conscience is taken for granted. Henry, who has clawed himself up from the lower class, can't afford to do the same.