Welcome To The Summer of Sterling Point

Dearest Darlings of Dames Nation,

Let’s talk about Sterling Point. I’m fired up about it, and I think you may become so, too!

Sterling Point is the latest series in Prime Video’s YA romantic drama niche, taking its very obsession-worthy place just this week among the streamer’s successful stable of shows like their adaptations of The Summer I Turned Pretty and the Off Campus novels. (It’s also the latest project from Megan Park, the Canadian writer/director behind My Old Ass, which is quite an impressive coming-of-age narrative pedigree.)

Having long since come around to the belief that weekly episode drops are superior viewing experiences and better for the health and longevity of individual TV series themselves, it’s the rare series that makes me endorse the choice to drop the entire season for binging purposes. Sterling Point’s first season (which I hope will be followed up by another two or three seasons) is optimized for binge-watching, followed by minute re-watching with friends. To call Sterling Point a teen drama is too shorthand-y, though; it’s a drama about and for teens, and is rich with many of the features we’ve been trained to expect from that genre. We’ve got pining! Romance! Secrets! Snappy dialogue! Finding oneself! Heartbreak! Conflict with parents who just don’t understand! Unexpectedly profound new friendships!

All of this to say, Sterling Point is both juicy as hell and is well worth spending time with, so I will be recapping it right here at Two Bossy Dames. Episode 1 is below; Episodes 2 and 3 will hit your inboxes on Monday and Wednesday respectively, with the remaining five recaps appearing weekly on Wednesdays thereafter.

This is bonus content alongside our weekend issues, so: the first three recaps will be available to all, with the rest behind the paywall. Let’s go!

Sterling Point Episode 1 Recap: Annie’s Coming to The Cottage (sorry, had to)

Annie Jacobson, 17 going on 37, daughter of Brooklyn, attends to her toilette in exactly the way you’d expect someone who is on the sharpest imaginable tenterhooks regarding their acceptance to the Wharton School of Business’s summer program to attend to their toilette: with rigor and minute attention to detail across many steps. Hair: washed. Body: scrubbed. Legs: shaven. Face: washed, toned, moisturized, gua-sha-ed. Hair, again: blown dry. She’s perched at the island in her massive kitchen in front of two laptops and her phone, dressed in what looks like a Brooks Brothers shirt she stole from her dad (adorable) and nursing some coffee in anticipation of Theee Most Important Email of her young life to date when her fraternal twin, Connor, ambles in.

Connor behaves in all of the ultra-casual ways you’d expect from a younger (by a few minutes, but still!) sibling of a high-achieving, type-A nightmare (loving; I see myself in her, minus the interest in business school). He’s muttering to himself a bit, wondering aloud about why Annie is “tweaking about a summer camp”, and almost literally smacking his lips over the bagels their dad Steven has brought home from Russ & Daughters1. Steven, you’re all right by me.

Connor gets to pose the season’s most essential question to his twin: “You’re 17, you’re acting like you’re 30. Don’t you think you’ll regret not spending the summer just going buck wild?” Well, congratulations, Connor, your sister is going to have the opportunity to answer that very question, thanks to Annie not getting into Wharton’s summer program, and thanks to the two of you inheriting a cottage and the island it sits on up in Lake Muskoka, Ontario!

It’s very kind of their late grandfather Gordon’s lawyer to have schlepped down from Ontario to bring them the sad news of Gordon’s death and the happier news of their inheritance, but they never knew the guy. The twins’ mother died when they were very young, and according to Steven, their maternal grandfather was kind of a big jerk. In fact, each detail the lawyer shares and the kids’ surprise at each one yields a troubling transformation in Steven. Where he’d been warm and supportive moments earlier, he shuts down entirely and gets real squirrelly, announcing that “nobody here is Canadian!” and snatching letters from Gordon to Annie and Connor out of the lawyer’s hand. Steven, you are officially no longer all right by me!!

I’m not sure how Steven did not predict the next sequence of events. Sir, you have raised your highly inquisitive daughter, have you not noticed how tenacious she is? Without highly programmatic summer plans, what’s she to do but turn her curiosity towards the letters you stole from her and Connor? None of Gordon’s actions fit the description Steven’s always given about why they don’t have a relationship with him; a mean old guy doesn’t hand-write letters to his grandchildren. He certainly doesn’t hand-write heartfelt birthday cards to them each year, and a secure father doesn’t hide those cards in his personal safe for years. Harrumph!

Wholly dissatisfied with Steven’s non-answers to her questions about Gordon and the titular island of Sterling Point, Annie jets off to Toronto and then seaplanes on up to cottage country with the adorable Ellis.2 DANG, Lake Muskoka and its environs are gorgeous, and as we fly in, approaching Annie’s cottage (which she lies about to Ellis, saying she’d rented it off Airbnb) we can see how diverse the housing stock is; some is super-luxe, and some is far more normal-looking. Turns out Gordon owned not just the house but the entire island, including the marina where Ellis works. [*low whistle of not bad, not bad at all, Gordon*]

Inside the house, we see that Annie may actually have two native habitats. Gordon’s house is full of sunbeams, framed informal family photos, warm wood paneling, and odds & ends belonging to Annie’s mom (which Gordon, tellingly, never threw away). It’s also full of acorns thanks to the squirrel who comes and goes via a permanently open window in the kitchen. Rusticity!

Since Annie has to get back to the mainland to buy groceries and needs a boat to do that, we’re treated to a parade of new characters, including both of Ellis’s parents (his caring silver fox dad, Joe, runs the marina – I wonder if Annie and Connor are now technically Joe’s bosses if ownership of the marina transferred to them along with the rest of the island) and Oona and her little sister, Maple. Both girls are wildly precocious in diverging ways. Oona is relentlessly flirtatious, but in a warm and playful way (which is to say, in the correct way) while Maple is wise beyond her years, given to witty takedowns of her sister, and can always be found with her nose in a book.

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Both Joe and Maple register strong, banter-laced reservations about Oona giving Annie a boat-steering lesson, but despite their concerns being 100% on the money, the two of them somehow survive the super-fast water donuts she teaches Annie to execute and make it to shore, where they pick up both groceries and Sully, who is only too happy to comp their order and skive off work from his mothers’ store in favor of hanging out with the girls. Sully and Oona, who was born in Amsterdam but is “basically from wherever my mum’s boyfriends are”, catch Annie up on the social shape of things in the area – how many locals rent out their cottages in the summer months at sky-high rates to wealthy tourists (good for them!), others sell, and buyers from out of town tear down the old cottages to build mega-mansions. Turns out, Gordon could have sold the island for millions, but never did, forgoing increasingly massive paydays, so everyone’s kind of nervous to learn their fates now that he’s dead. At least the celebrity vacationers are gossip-worthy; Oona clearly dines out on an anecdote about Kaia Gerber winking at her and maintaining sustained eye contact from her dock the previous summer.3

Whether Kaia did or did not wink at Oona, there’s no denying Oona’s eye for vibes between people, as she instantly registers that she has no chance at all with Annie when Ellis arrives to take everyone to a spot where they can kayak and splash around for a bit. Fear not for Oona’s romantic fortunes – I’m sure her “a beautiful name for a beautiful girl!” line has worked before and will work again. She’ll have the opportunity to test it out in no time, as they all immediately agree to Sully’s suggestion to drop in at a party at a cottage owned by some big real estate out of towners. Off they go, and Annie quickly finds that the big real estate people in question are the parents of – son of a gun!! – Rory, a sweetheart with floppy 90s boy band hair and a boyish version of Billie Eilish’s face, who simply can’t believe he’s seeing Annie J from middle school in his parents’ boat house!

Speaking of Rory’s parents, it turns out that his mom, Denise, is also at the party. His mom. Is at the party. Where the teens are drinking. I realize that this is me showing what a rube I am, but I can’t tell whether this is Rory’s party and also his mother is there, wine mom-ing it up, or if it’s Denise’s party, and she’s of the “we’d rather you drink at home” school of parenting. Denise is played by a perfectly cast Missi Pyle, who can always be counted on to deliver a note-perfect performance in this kind of role, and she is so happy to see Annie, and she wants to know if anyone was there for Annie when she first got her period. It’s clear from Annie’s face that there was not, and that this girl, who is so pulled together and matter-of-fact about having grown up without a mom, is starting to really feel the weight of having had to navigate girlhood without grown-up girls to rely on for advice and support.

Annie is ravenous for information about her late mother, but is kind of bowled over to learn that Denise and her mom were really close way back when. Denise first learned about Muskoka because of Goldie, and further, she “was so upset that she couldn’t be with you and your brother; I think that’s what finally led her to file.” File for what? For divorce?! Wait, didn’t Goldie die of cancer, still happily married to Steven? What?! Annie is experiencing an absolute emotional blitzkrieg right now. Oona remains extremely on-brand by taking a quick moment to flirt shamelessly with Denise before leaving with Annie, Ellis, and Sully, prompting an immediately classic mother-son exchange between her and Rory:

Denise: Is she the one who makes out with all my friends?

Rory: Yeah.

Denise: Have I made out with her?

Rory: Not yet! Let’s get you inside.

Post-fireworks, (Happy Canada Day!) Annie’s acceptance of a total lack of cellphone service continues to develop as Ellis walks her up to the house. Seconds after Ellis has left, reassuring her that she’d be fine, Annie is shocked to discover another teen girl in the kitchen who immediately stalks up to her, demanding (not unreasonably) “Who are you? What are you doing in my grandfather’s cottage?!” Annie’s got some ’splaining to do!

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Not To Put Too Fine a (Sterling) Point On It:

• Kaia isn’t at the party, Denise explains to a disappointed Oona, because she got food poisoning at the Beckhams’. Innnncredible detail, made possible by Kaia being unavailable for even the tiniest cameo due to her shooting schedule for The Shards, which also debuted this week (on F/X). This is my headcanon, anyway!

• Joe’s conversation with Gordon’s lawyer suggests that he knows an awful lot more about Goldie and her family than he’s let on to anyone else. Are we finding yet another grown-up at whom I’ll be lavishly rolling my eyes?

• Good needle drops are harder to pull off than you might imagine, and while singling out the very first one in the very first episode for some praise is the easiest choice to make, it’s also a really good choice. Choosing to score our first scene with Annie to “maggots for brains” by Olivia Rodrigo (beloved of this very newsletter) is another easy choice that’s also sneakily brilliant. Rodrigo’s latest album, you seem pretty sad for a girl so in love, is packed with Songs Of The Summer material, many of them (including “maggots for brains”) quite sad under a veneer of pop shininess. Annie herself appears at first glance to be one kind of girl – the kind of girl who had an internship in 6th grade and who needs to be encouraged to go buck wild in the summer before her senior year of high school – and is very likely to figure out she’s also another kind of girl over the course of this summer up at Sterling Point.

• Speaking of Annie’s Canadian excursion, it’s just as well that there’s no reception up there, because otherwise her dad would be onto her cover story immediately. Jetting off to Thailand with her (definitely gay but not out) boyfriend Oliver is so flimsy, and informing her father of it via a Post-It on the front door is beyond. At the same time, though, I’m cheering. Good for you, kiddo! If a surprisingly wholesome sojourn at Lake Muskoka is your version of going buck wild for the summer, then keep on going.