Rob Brooks, a female record store owner in the rapidly gentrified neighborhood of Crown Heights, Brooklyn revisit past relationships through music and pop culture, while trying to get over her one true love.
After a first date and hookup gone wrong with nice guy, Clyde, record store owner, Rob Brooks, goes into an emotional tailspin in which she recounts the ups and downs of her All-Time Top Five Most Memorable Heartbreaks: childhood sweetheart Kevin Bannister, cool girl Kat Monroe, guy who gets her Simon Miller, off-limits Justin Kit, and perfect match Russell "Mac" McCormack. Rob also reveals the impact of an unexpected encounter.
As Rob builds a playlist to send to Mac and work through her feelings, we explore the mythology of their relationship, and hint at the reason for its demise. Rob goes to a concert with her employees/friends, Simon and Cherise, where she meets a musician, Liam – who might just be the distraction she needs. Right when she is starting to feel better, Rob gets some surprising news from her brother Cameron that sends her spinning again.
Rob obsesses over Cameron's big news about Mac, falling deeper into the rabbit hole when Cameron lets slip another detail that makes things worse for Rob. She finally finds sympathy for her predicament in an unexpected place: Liam. But when her night with Liam ends with a thud, Rob realizes she may be stuck in a pattern that only she can break and decides to do something about it by revisiting her past.
In hopes of understanding why her relationships continue to fail, Rob decides to track down her All-Time Top Five Most Memorable Heartbreaks. It starts out as a satisfying romp down memory lane, giving her the answers she wants from Kevin Bannister and Simon. But at an Instagram influencer party hosted by Kat, she gets an answer that (briefly) shakes her resolve, before going to have the one conversation she's been avoiding: finally confronting Mac about their unfinished business.
Rob is ready to move on to the next chapter in her life, so when she gets a call about a record collection for sale she asks Clyde (her one-nightstand) to go with her to the Upper East Side. Due to the interesting circumstances around the collection's sale, the day turns into an adventure and they forge an unexpected friendship along the way, ending in a sweet gesture from Clyde — but is friendship really what either of them wants?
Rob reconnects with Liam when he returns from tour. His band has blown up and Rob is caught in the fantasy of dating a musician – going to the recording studio, spending a night backstage as his date, etc… But the reality of what Clyde is offering – be it friendship, or something more – acts as a counterweight. Simon develops a crush. Cherise helps Rob track down two shoplifters, who end up inspiring Cherise to pitch herself to Liam's rep, which doesn't go as expected.
Cameron drunkenly decides to throw a "Last Hurrah" party at the dive bar before the baby arrives after he starts to worry about how much having a baby will change his life. Rob arrives and is shocked to find Mac and his fiancée, Lily. To get through the awkwardness she calls Clyde for back up. Things get complicated when people think Clyde is Rob's boyfriend and true feelings inevitably bubble up…
It's Simon's turn to recount his All-Time Top Five Most Memorable Heartbreaks. We follow Simon back through the good and bad of his dating life since he came out, all of which might explain why he is so nervous around his Barista crush, and how he became so jaded about love. But is he able to get the closure he needs to move on?
A milestone birthday drives home for Rob just how stuck her life has really become. She tells Simon and Cherise she plans to spend her birthday by herself, but changes her mind after a call from her mother. A surprising night out with old friends leads her to a rooftop confrontation with an unexpected well-wisher, that ends with the moment we've been building to all along – the reveal of what really brought about the demise of her relationship with Mac.
Rob reflects on the night of her birthday, where we learn she finally got clarity on her feelings about Mac. Cam and Nikki's baby finally arrives, prompting Rob to finally take a chance and go after what, or whom, she really wants. In going out of her comfort zone, and seeking to right some wrongs, maybe she can let go and finally stop her past from messing up her present. Meanwhile, a surprising gesture sets Cherise on a path to make her own music.
