Hannah is still trying her best to keep the evening civil at her dinner party. She asks Ray an innocent question: Where is he living now? Ray can't give her a straight answer. Something about his aunt's, something about crashing with friends. Shoshanna chimes in that he stays with her a lot, and then she starts to put things together. He's stayed with her for at least the past three weeks, and she asks point-blank: Do you live with me? And in one of the sadder moments of the series, Ray admits that he lives in his car when he's not staying with Shoshanna.
On the subway platform on their way home, Shoshanna is rightly upset, but not for the reasons we'd all think. She's upset because she missed a major life event: knowing and participating in the decision to live with your significant other. Shoshanna starts to wonder out loud why someone his age wouldn't be able to afford an apartment, and why he doesn't have more interests or passions. And we get to the heart of Ray. For all his talk, his confidence, his ability to judge everyone else, he really and truly believes that he's just a loser. He's a homeless 33-year-old dating a lovely 21-year-old. And he kind of hates himself. When Shoshanna says she's falling in love with him, he says that it's way too early for that. She looks devastated and reprimanded. But moments later he admits that he's "so f---ing in love" with her too.
Meanwhile, Jessa and Thomas-John are getting ready for dinner with his parents. They've seemed unbelievably happy so far, but we haven't seen all that much of them, so it's a little hard to evaluate. At dinner we find out that this is the first time Jessa has met her in-laws. And these do not look like the type of people who would be thrilled about their son running off and marrying the bohemian girl he's only known for a few days. The dinner starts off in a civil manner, but things turn quickly. Jessa is very frank about her life and experiences, telling his parents that she in fact only spent a few months at Oberlin College and that she went to rehab for heroin use. His father seems smitten in a fetish-y way, and his mother wants to tear her down and get at her true motives. She assumes it's money. Not that long ago, it wouldn't have been a strike against a non-working woman to marry a wealthy man. But now, it's cause for suspicion.
When Jessa and Thomas-John arrive back at his high-rise, they start to fight. He's upset about how forthcoming she was. She's upset that he'd already placed so many restrictions on her conversation topics before they left (returning the puppies, tattoos in Mexico, etc. were all off-limits). The fight turns into something else, though, and they both get to the heart of what was never going to work in their relationship from the beginning. She thinks he's conventional. He thinks she's a freeloader. End of story.
"It's A Shame About Ray" ends with Hannah singing "Wonderwall" in her bathtub. Jessa, who's just left Thomas-John's and, presumably, her marriage, walks in and joins Hannah in the tub and proceeds to cry. Perhaps she really did like her life with Thomas-John, or maybe she's upset to be thrown back into uncertainty. Either way, it's affecting.
Hannah also had her Rayanne moment this week. She and Marnie have been quarelling for a while now, sometimes passively, and sometimes out in the open. But tonight, she stood up for her to Charlie. It was a little too late, but still, it was sweet -- she clearly still cares about Marnie.
So, what do you think about Jessa? Do you believe that money was ever a factor in her decision? Is it possible that she's so privileged that she doesn't even realize it? And what about Shoshanna and Ray? It seems like overall his full disclosure will be a positive, but, as embarrassing as it is, why didn't he just tell her that he was having trouble with money?
Note of the Night: Former Lemonheads member Jesse Peretz directed tonight's episode (along with a number of others), named after a Lemonheads song. Peretz had left the band before the song was released, but he did direct the music video for "It's A Shame About Ray."