While Girls is supposed to be about twentysomethings taking their first stabs at adulthood after college, the older people surrounding them—like Ray, Booth Jonathan, Thomas-John, or Marnie's 40-ish ex-boss who wears pigtails and clothing made of scuba suit material—serve as proof that insecurity has no age limit. It's frightening to learn that we might never grow out of it, but also comforting to know that we all suffer from it, if only occasionally.
Up until this point, the show had been about these characters trying to figure out not just life, but who they are and what they want. Now, they're kind of getting what they thought they'd been longing for, and realizing that it's not as great as they thought it would be.
Case in point: Hannah and her e-book. The episode opens with a stroke of good fortune. Some literary idol of hers (played by John Cameron Mitchell) decides to make her his prodigy and gives her a "deal" for an e-book. It's not really known if this deal included any money, although the assumption is that it didn't because she still has to mop the floor at Grumpy's. So thrilled with finally being asked to do what she said she always wanted—writing—she doesn't think she's allowed to turn the project and its ridiculous deadline (one month!) down. She wants to be happy about it, but instead she pukes and then procrastinates.
Jessa, who is in the midst of depression over her failed marriage, has the best advice for Hannah:
Whether you write this book or not, it's not going to change anything. This book doesn't matter. That's the first thing you need to know. It's not gonna matter to the people who read it, or to you.
It sounds really mean, but it's actually the best way to actually get to work writing something. By placing too much (self-assigned) importance on what you're doing, you could get anxious and nervous and gum up the works, making your task that much harder because you're so worried about falling short of your own expectations. But by letting go of any pretense about your work, you can actually find yourself typing your ideas instead of freaking out about whether they're any good.
Like Hannah's book, Marnie's relationship with Booth was also virtual. The sex and the hanging out and all of that could be described as a relationship, but not everybody would define it that way—namely Booth. It wasn't really real. But Marnie was more in love with the "idea" of Booth and his lifestyle than with the man himself, a revelation that caused him to have a toddler-like temper tantrum, crying about how he's not important and he hates everybody. She thought that his life was so attractive and that it was what she wanted for herself, but seeing what a mess Booth was shattered her fantasies like the wine bottles he broke in his comic meltdown.
Speaking of babies, Ray and Adam take an improbable trip to Staten Island to return a dog that Adam stole from somebody there. Their day together—which began because of Ray's missing copy of Little Women—ultimately revealed them to be nothing but Big Boys. Both are immature and have stupid ideas about women and even stupider metaphors about Staten Island. But Adam, in his weirdness, continues to be the most mature and emotionally astute of the bunch. (My favorite Adam quote from season one was when Hannah told him "I don't want us to outgrow each other," and he replied, "That's on you, kid. I ain't done growing.") He said what I'd been thinking about 33-year-old homeless Ray's relationship with 21-year-old Shoshanna:
"You don't know shit about love. What you're doing with Shoshanna is not real. She's just some kid you feel safe with because you know it won't work out. You're just babies holding hands.