You can take the girl out of New Jersey...but her suburban friends will find her anyway

By Amy Wilkinson
February 03, 2016 at 11:37 PM EST
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S2 E5
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Do you remember that one episode of Friends in which Ross — allegedly on a break from Rachel—has sex with Chloe the Copygirl? And is pretty sure Rachel won’t find out? Until Chandler’s all like, What about the trail? And Ross is all like, What’s the trail? And Chandler’s like, Idiot — it’s the people between the girl you slept with and the girl you never want to find out about it. Well, Liza’s finally (truly) considering the trail between her 40-something life and her 20-something persona. The overlap is becoming problematic, and Josh is right in the middle of it.

It starts when Liza’s daughter — carefully-tucked-off-screen Caitlyn — follows Josh’s band on Instagram. Liza doesn’t want Caitlyn getting too close to him until she knows whether this relationship will last. And the trail only gets more tangled from there.

Later that night at one of Josh’s shows (reminder: he plays the washboard, and I’m not referring to his abs…), Liza runs into her New Jersey friends Michelle and Tom, who are taking a field trip outside the suburbs to see the band (which they learned about via Caitlyn’s Instagram). Sporting a “truffle butter” shirt (because she likes to cook with truffle butter, obvi), Michelle breathlessly inquires about Liza’s younger man.

Chimes in husband Tom: “I think someone is buying real estate in Cougartown!” He then invites Liza and Josh over for dinner so they can see his new trellis. Josh enthusiastically accepts — partly because he’s curious about Liza’s pre-Brooklyn life, but mostly so he can find out what a trellis is.  

Meanwhile at Empirical, Kelsey is trying to coax pages (chapters!) out of her first and only Millennial Print author, the quixotic Jade, who’s more concerned with her book cover featuring her mid-orgasm on the subway than actually, you know, writing. #Priorities

Kelsey wants to publish in six months, and she insists Jade meet her that evening to work on pages. Unsurprisingly, the would-be author stands up Kelsey, who discovers via Instagram that Jade is #blowingmyadvance #chestypeters on python-skin boots and douche burgers (a wallet-suck of foie gras, lobster, and kobe beef smooshed between two buns). When Kelsey finally tracks Jade down at the Gramercy Hotel, she’s dealt this terrible blow: “Bitch, there is no book.” There goes Kelsey’s entire imprint budget for the year.

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Liza, for her part, isn’t having a much better evening in New Jersey with Josh. Friend Michelle pulls Liza aside for a heart-to-heart about the “boy toy,” a term which Liza takes offense to. They’re getting serious, after all! Not so fast, says her friend, reminding Liza that she’s just a middle-aged divorcee looking for validation. Not even Demi Moore could make a May-December romance work! And as much as we might want to say age is just a number and you’re only as old as you feel, you have to admit Michelle makes some valid points. Points that don’t come from a place of jealously or malice but logic. And the truth of her words hits Liza with such a thud that she unwraps the pot pop she’d confiscated from Josh and enthusiastically chomps and chews the sucker until it’s gone and she’s stoned.

Back at Josh’s place, after some prodding from him, Liza admits that Michelle got to her and that she has fears about their age difference. But Josh isn’t bailing.

The trail lives another day. 

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