“Ballad of the Lonesome Loser” opens with a flashback to “Me Time”: it’s the night of Cam’s Last Hurrah, and Rob is trying to convince Cherise and Simon to join her. They refuse, and she heads out into the night. Simon makes his way to the bodega, silently buys some gum from Carlos and then … breaks the fourth wall to share with the audience his Top Five Heartbreaks of All Time. Oh, boy, it’s going to be a standalone episode from an alternate character’s point of view!
This is the kind of TV you can create when your adaptation has the luxury of time, the freshness of changing up the gender, race, and sexuality of the core characters, and the strength of actors who can pull off any material you give them. It’s so delightful when a show has both the capacity and the freedom to surprise the audience like this, and the choice to showcase Simon is a good one. We get so close to his thoughtful perspective in other episodes that a deep dive into his backstory is a welcome treat. If you like this episode and want to see something similar, I recommend “Ne Me Quitte Pas,” the episode of Ramy told from his mother’s perspective. It’s worth noting that each of these standalones appear in nearly the same place in their respective shows’ ten-episode runs.
Let’s get into these heartbreakers, dream makers, love takers who’ve been plaguing the most insightful record-seller in Brooklyn.
Heartbreak #1 is Ben, who entered Simon’s life about a year after his “so-called breakup” with Rob. This almost-throwaway line incinerates Rob’s overinvested framing of their brief romance. The economy of it! Well written, well delivered. They’re hanging out at the club where Rob DJs and she asks for his input about what song to open her set with; after some back and forth they arrive at the Pointer Sisters’ “Automatic” as the right leaping-off point. I like that it’s upbeat but not as frenetically paced as “Neutron Dance” or “I’m So Excited,” so the DJ and dancers have somewhere to go with subsequent songs.
A handsome fellow in a black blazer cruises Simon at the bar, asks him to dance, and then asks if he’d like to go somewhere else since he thinks the DJ sucks. Hrm. They wind up at a drag karaoke bar, and while a queen sings “It’s All Coming Back to Me”, we learn that Ben (Christian Coulson) is a rather ambitious lawyer. Refreshingly, he’s not snobby and is unfazed by Simon working at Championship and being a communications-engineering grad school dropout. Kissing ensues, and we jump back to the present, where Simon explains what a pleasant change Ben was to him; after coming out, he’d really only had a series of one-night stands with guys who barely remembered his name. By contrast, Ben stayed in touch and remembered Simon’s last name. Being minimally attentive is a low bar for a suitor to clear, but it was intoxicating.
After spending nearly every day together for two months, complete with cute and witty texting, Ben just stops responding. Simon rationalizes it away, assuming that Ben dropped him because he’s “a loser who worked in a record store.” Rob’s tolerance for other people’s sad mooning over their boyfriends is hypocritically low and she deletes Ben’s contact from Simon’s phone. Allegedly it’s for his own good, but mostly it’s because she can’t stand how he’s obsessing over Ben’s radio silence. Not a great look, Rob!
Heartbreak #2: Benjamin Young, again! Unlike Rob, who goes around on the dysfunctional relationship merry-go-round with a new person each time, Simon seems to need to re-learn his lesson with the same unworthy guy on repeat.
This time, we don’t see how they got back together, just that they’re making out at the club while Soft Cell plays. It’s pretty standard and understandable: Ben apologizes for ghosting, Simon seems to be in a forgiving mood. In his mind, they’re just picking up where they left off, but that is not how STIs work. A trip to the clinic confirms Simon is HIV negative (yay!) and chlamydia positive (boo!). Thank goodness for antibiotics, but this is a dealbreaker to Simon, which leads us to…
Heartbreak #3: Knock knock! Who’s there? Yet again, it’s Benjamin Young!
Literally, he’s right there at Simon’s apartment door, a bunch of apology roses in hand. Simon slams the door in Ben’s face, but you know that’s not going to last. Simon’s a romantic who was born to be in a stable relationship, something he highlights to get Ben to understand the terms he needs to continue the relationship: “I’m too old to be confused like this, okay, it’s nothing to do with sex or monogamy. You have never committed to me, ever. You could just disappear at any minute, because I don’t know what the fuck we are!” Ben declares “nothing would make me happier than to be your boyfriend,” so voila, they’re official boyfriends.
They go to the Allied together, where Sylvester’s “You Make Me Feel (Mighty Real)” is playing on the jukebox and Ben is surprised that Simon likes disco, because “it’s so upbeat and poppy!” Simon delivers a really soulful little talk about little talk on disco’s cultural and social significance — “it’s the sound of liberation! Every early hip-hop song samples disco!” — and Sylvester’s influence as a genderqueer icon.
Throughout this scene, Ben gazes at Simon in full The Look mode, leading Simon to think it’s the right moment to tell Ben he loves him. Before Ben can respond, he gets a call from work, deflating the moment entirely. Sigh.
Heartbreak #4: Is it a new-to-us fellow named Timothy Marshall? Nope, it’s Ben. This heartbreak isn’t preceded by a breakup, highlighting that heartbreak can happen in the context of an ongoing relationship.
Simon is hanging out in Ben’s amazing, light-filled, balcony-featuring-views-of-the-Brooklyn-Bridge apartment. Ben finally tells Simon he loves him, and that he’s made partner at his firm. Hooray! His colleagues are throwing a party to celebrate that night, so Ben bought Simon a fancyish shirt to wear, “because you don’t own any shirts younger than Betty White.” Ben goes for a triple play now, suggesting that Simon move in with him and quit working at the shop, so he can go back to grad school, or find whatever his passion is. On some level, Ben really isn’t cool with Simon as he is, but that’s too much to get into just now, especially since Simon has just noticed an incoming text from someone named Sam that reads “see you tonight, hot stuff ;-)” What the hell?
A word about the shirt: throughout the episode, Simon has been on the hunt for this particular shirt. It’s a plain, light gray short-sleeved button-up shirt. I’ll say this for Ben, he nailed it with this choice, which is several steps above Simon’s usual vintage band T-shirts, but not so far out of his comfort zone that he feels self-conscious in it. Unfortunately, one of Simon’s roommates — a trio of hot, mean gays named River, Dallas, and Link— wore it to a party recently and it’s ruined. He needs a new elevated basic, but all that’s available is a shirt in the same style but in a loud print that makes him “look like a bully in an ’80s movie.” Oh, dear.
At Ben’s party, Simon is in his head, stewing over the text from Sam, so jealous and suspicious that he downs a huge whiskey in the bathroom and then wrongly accuses Ben of taking up “with this elderly thirst trap” (just a regular colleague, turns out). Ben, mortified and furious, explains that Sam is the woman whose office adjoins his, not someone he’s cheating on Simon with.
Simon: “The thing about me is, I’m pathologically insecure.”
Me: “Now that’s what I call a moment of clarity!”
Heartbreak #5: to the surprise of literally no one, it’s Ben! Turns out, that very day, Ben swung by the shop. He misses Simon and hopes they can renew their relationship. He said all the right things, but after reflecting on all the heartbreaks of the last couple of years, Simon “realized if I want a shot at being happy, I’m going to have to take a risk, and Ben just wasn’t the risk I wanted to take.” Oh, happy day, he’s going to see the Cute Barista!
Simon, clad in his terrible shirt, rolls up at the coffee shop at closing time. After a little cute banter, the pair stroll into the evening together, full of hope and possibility. Across the street, we see Rob sitting on the curb outside The Allied, glumly smoking alone. Hats off to High Fidelity for giving us an episode where the most sympathetic character gets the happily ever after he so richly deserves, and for doing so while shoring up the themes of the show.
1) Song of the episode: Sylvester’s “You Make Me Feel (Mighty Real),” by a country mile!
2) Speaking of Sylvester, Simon’s impromptu talk about him is what good musical expertise is all about. If you know your shit, use it to give others a bunch of entry points to the things you love. Simon’s not a culture hoarder, he’s a culture sharer. Let’s all be more like Simon.
3) Christian Coulson, who plays Ben, has a look I can only describe as “Mayor Pete crossed with Chris Parnell” and now I would give anything to see him do an impression of Mayor Pete doing an impression of Dr. Leo Spaceman.