How the flim-flamming flip-flop did Toby Fleishman wind up here? Here, in his kitchen, holding an overpriced, rotting quarter of a watermelon? In-season watermelons are delicious, but as the saying goes, they’re also abundant and low-value. $14.99 for a pitiful quarter of a watermelon in high summer? Not in a region awash in reasonably priced, high-quality produce. But also, more existentially, how did Toby get here, holding an overpriced, rotting quarter of a watermelon, which is 100 percent a metaphor for the absolute state his life is in these days? Welcome to an episode told almost entirely in flashback. Oh, and grab some Kleenex — this one is trying to break your heart.
It’s painful to watch good love go bad, but what if we’re watching a good-faith delusion go bad? I don’t have a straightforward answer for that just yet, and I suspect I may not until I watch the last frame and reread the last paragraph. There’s no question that Toby and Rachel meet cute, at one of Seth’s parties up at Columbia Business School. Toby and Libby spend most of their time observing and narrating — in flawless imitation of David Attenborough — Seth’s flirtation-with-intent with a hot Israeli, but eventually Toby decides to brave the punch bowl. Rachel is close by, watching the nature documentary unfolding before her as Toby was doing with Libby, but she’s doing so alone. She’s pretty, he’s cute, all it takes is a little negotiating-as-flirting banter and, bam, they’re in the middle of a very sweet dirty weekend, which swiftly blossoms into something permanent.
The full negotiation exchange is worth looking at in a bit more detail with the benefit of hindsight: Rachel warns Toby she’s going to beat him; he tries, anyway. She makes an offer, he counteroffers, she walks away, he can’t resist following her and whispering a counter-counteroffer of all she wanted and more, and who could resist someone placing the world at their feet like that? This, the very beginning, where everything is potential and nobody is seething with resentment and contempt, is a high-water mark for their entire relationship. Rachel is very upfront about what she wants: After a youth spent with an emotionally remote grandmother on a very tight budget, financial security is No. 1 with a bullet. Toby, having never considered in significant detail what he imagines his future life as a doctor, husband, and father will be like, projects his inchoate hopes onto her and dives in, assuming things will turn out for the best, just as they always have done.
And they do, for quite a while, but the warning signs are there early on. Not nearly as much about Rachel as about Toby. He either can’t or refuses to see what’s right in front of his face. Toby knows Rachel is an orphan, that she was starved for the parental affection necessary for her to form secure attachments in other relationships. He knows she thinks he ought to go into a medical specialty that promises a decent work-life balance and the highest possible income. How does he not notice her marrow-deep need for the security of having an executable plan? How could he miss the difference between his blithe “It’ll all work out”–ness and her “Well, sure, maybe, but only if we make certain that it does”–ness?
One does not pluck from obscurity and nurture the Broadway-conquering career of an Alejandra Lopez (Rachel’s main client as a theatre talent agent) if one has not read every periodical published in the five boroughs, including The Canarsie Courier, which is the only one that’s mentioned Alejandra Lopez and her eventual breakthrough one-woman show, Suffrage Monologues. Rachel is not just dogged, not just a skilled negotiation shark, not just someone with an eye for talent. She’s all of that and ever so slightly desperate for success to boot. It’s a potent combination, but it doesn’t make for a life grounded in values congruent with Toby’s.
He believes his values are the best, and is baffled that Rachel doesn’t subscribe to all of them once he explains how right they all are. Toby is A Good Person whose career choice is a righteous one. If he spends his working life doing good for his fellow man, that’ll be a life well-spent, an end in itself. Tell me you are a comfortably middle-class person who received a traditional Jewish education without telling me, etc., etc. That’s my background, too; I get it, this stuff runs deep! What I don’t get is how Toby fails to grasp the difference between making life choices on the basis of one’s ethics, and expecting one’s spouse to make the exact same choices, purely on the basis of their righteousness.
Righteousness alone, as Rachel might put it, isn’t necessarily going to put dinner — something other than steamed chicken and vegetables, for Rashi’s sake! — on the table. A doctor’s salary, even in a rarefied specialty like hepatology at a prestigious Manhattan hospital, won’t cut it. It’s not going to pay the tuition at the elite private schools she intends their future children to attend so that they befriend other children born into privilege and pursue higher education at elite institutions, from which they can graduate into elite professions (not medicine; medicine entails working too hard, and visible effort is for strivers, not for the elite). She wants them to be able to move through the world with as many barriers as possible preemptively removed by the generational wealth she hopes she and Toby are building. Rachel has some understanding of what it feels like to hustle, and it’s been powerful fuel for her ambition, but she also feels what a burden it is. Like many parents — like Toby himself — she wants her kids’ lives to be better than hers has been, and the factors she’s identified as life-improving are money, geography, and connections. The latter two flow from the first, so she gets cracking. And she stays there.
Rachel stays in fifth gear professionally even after having Hannah and Solly, going so far as to found her own theatre agency as her first act after abruptly concluding her maternity leave. It’s an impressive, bold career move, raiding her former agency of its best clients (including Alejandra Lopez) and staff, with profitability not far behind. And what does she have to worry or feel guilty about? Hannah is in great hands with Toby and their lovely nanny, Mona. This arrangement is best for everyone: Toby can be virtuous, Rachel can make the money she knows they’ll need for the future, and Hannah will thrive. Everyone is doing the things they are best at, and she doesn’t need to occupy herself with thoughts of being a deficient mother. She isn’t a deficient mother, but the combination of a truly harrowing birth experience and her anxiety over lacking the mothering skills she observes in other new mothers is too much to bear. Work, she knows how to do: The year Solly is born, three of her agency’s clients open shows on Broadway. She’s unstoppable! Leaning in!
It’s fascinating how even though this episode is narrated by Libby, and she’s on Team Toby, flashes of skepticism about him and sympathy for Rachel creep in. Rachel fights dirty, cruelly, and we flinch at that. We flinch, too, at how Toby is always taking out on Rachel his seething, petty resentment of the other dads in their social milieu. They seem like some of the most boring people alive, so who cares what they do or think, but Toby can’t shake off their patronizing comments about his career and easy embrace of his role as the primary parent. Masculinity threatened, Toby can’t stop making incidents like Rachel being sexually harassed at work about himself. Fleishman, a lot of your being in trouble is caused by your inviting trouble.
Other small, humanizing details make their way into Libby’s narration. During Rachel and Toby’s first weekend together, they’re swapping core stories about themselves — where they grew up, what their families are like, their favorite songs. Rachel has just one memory of her late mother — not a specific event, more of a sense memory, but it’s enough to sustain her lifelong belief that pining for her mother must mean that she was loved by her mother in turn. (I did say you’d need Kleenex for this episode.) God, this poor girl. Raised by her late mother’s mother, who was no doubt clinging to the idea that doing her duty while stricken by grief was the best she could manage — this is some real Emily of New Moon stuff!
No wonder Rachel finds Toby’s intact family and their weekly Shabbat dinners intoxicating — “You’re so lucky to have family,” she whispers. Being surrounded by people who snipe and hassle, sure, but people, nonetheless! People who care about you and say so! What a concept! No wonder she’s ambivalent about her pregnancy, no wonder she feels that she can’t bond with or soothe the infant Hannah, no wonder she falls back on practical financial considerations as her primary method of showing that she cares. And oh yeah, her substitute OB assaulted her during labor by stripping her membranes without requesting her consent. Giving birth is hard enough under ideal circumstances. Being obliged to put the safety of your child’s entrance into the world in the hands of someone who already harmed you at your most vulnerable moment is a gold-plated mindfuck. No, thank you.
Fast-forward to an awful dinner party where Rachel, not understanding that choosing an unattainable famous person is crucial for your Free Pass not to destabilize your entire relationship, names Sam Rothberg. Sam Rothberg?! That vapid brunette James Van Der Beek–looking guy who doesn’t even do anything worthwhile with his life? The one who tried to lure Toby into working for his pharmaceutical company? Wait, could Rachel be with Sam Rothberg right now???
• Toby and Rachel’s first meeting is not unlike Claire Danes’s iconic love-at-first-sight scene with Leonardo DiCaprio in Romeo + Juliet. The not-at-all subtle needle drop of “Tonight, Tonight,” by Smashing Pumpkins, fairly screams “meet-cute incoming!!” but it’s not just that. Rachel’s cute printed top, featuring a Japanese painting of fish, seems like a visual callback to the fish tank through which the doomed lovers first catch each other’s eye, and the (all too brief) banter that makes everyone else at the party fade into insignificance crackles very nicely indeed.
• Special shout-out to Jesse Eisenberg’s line readings that thread the needle of neutral curiosity with a scorching filament of passive aggression. They’re all good, but his “Is that … formula?” upon arriving home the day Rachel founds her own agency is pure gold.