Dean Di-Laurentis, Off Campus. A true wingperson is like a sincere sports coach. They’ll spot potential in someone, and drive them to be the best version of themselves. That’s what Dean is to Garrett. Dean earns his stripes by being the loudest cheerleader for his friend’s romance, without ever making it crass. When Garrett seeks him out for advice on being intimate with Hannah, Dean is the one who has tips on trust and consent. Top-tier stuff.
Event Context
Enid Sinclair, Wednesday. Enid is Wednesday’s Dr Watson — bridge between her and the social scene, counterweight to the sombre introspection, cautious enabler of adventure. In S1, Enid notices Wednesday’s interest in Tyler Galpin long before she even admits it to herself. That Tyler turns out to be a blood-baying monster is a different story. But Enid’s instincts have been spot on. This kind of meddling we like.
Peter Parker’s Stark suit, Spider-Man: Homecoming. Long before AI and ChatGPT started (mis)advising teens, sweet-natured Karen was living inside 15-year-old Peter Parker’s Stark suit. Peter was juggling school and superhero duties. Karen was the one who tracked how his heart races every time Liz walks by, and pushed him to step up. After Peter rescues Liz from the Washington Monument, Karen urges him to seize the moment with: “This is your chance. Kiss her.” He doesn’t, but that’s OK.
Perrito, Puss in Boots: The Last Wish. Dogs as wingmen? Obvs. And there’s no better therapy dog for the anxious Puss than Perrito, who unknowingly engineers the reunion of Puss and Kitty Softpaws after he abandoned her at the altar. Perrito urges Puss to rise above his fears and be vulnerable with Kitty, prompting him to work through their differences. And all along, he doesn’t have a single wish for himself. Really, we don’t deserve dogs.
Team Analysis
Lady Danbury, Bridgerton. An underrated but critical part of being a good wingperson is to be all up in the company you keep. Lady Danbury knew this well, and knew the ’ton too. She wasn’t simply making strategic alliances within Regency London, she was playing Cupid. Who else will remove the pesky obstacles (Simon’s father’s toxic legacy, the Kate and Anthony failed-wedding scandal) so that two people might find love? Stay on her good side, or you’ll never be wed.
Dr Watson, Sherlock. Not a usual suspect. But enough of a bestie, punching board, collaborator, sober companion and voice of reason that he’d be a good filter, should a woman catch Holmes’s eye. When our “high-functioning sociopath” gets interested in Janine Hawkins in S3 (only to get closer to his arch-nemesis, Charles Magnussen), sweet Watson never stops hoping it will turn real. Wingpersons soften their buddy’s sharp edges. It’s a job Watson was born to do.
Steve Harrington, Stranger Things. What a character arc! Steve is a random jock in S1. He gets promoted to being babysitter to meddling kids, then to baseball-bat-wielding hero in the monsterverse, then to a hopeful third wheel with Nancy and Jonathan. All through, he’s the dude with the best advice on living and loving large. In love and war, having Harrington in your corner makes all the difference.
Pascal, Tangled. OK, this is a chameleon. He lives on Rapunzel’s shoulder and is also cut-off from the outside world. He’s literally her wing. Pascal had reservations about Flynn Rider in the beginning. He was protective of her, keeping a close watch on Flynn’s moves. But who keeps pushing the two into romantic situations? The little chameleon who has no lines of dialogue but plenty of smarts.
Match Outlook
Courtney Rockliffe, The Sweetest Thing. The key to being the best wingperson is to be selfless. That’s what Courtney was to her friend Christina. When Christina confesses to having fallen for Peter, Courtney is the first to tell her that this is more than just a crush. She makes it her mission to ensure her bestie meets the love of her life, even if it involves a cross-country search. Courtney could have made it about herself. Instead, when a friend took a chance on love, she came along for the ride.
Jacob Palmer, Crazy, Stupid, Love. Palmer is an elite wingman. He understood right in the beginning that romance couldn’t exist without confidence. So, when he meets the crestfallen Cal Weaver at a bar, he knows what is needed. A makeover, a wardrobe overhaul, essentially TLC for the body so that it seeps into the soul. Jacob was more of a life coach to Cal than a wingman, teaching him about self-acceptance and not seeking validation elsewhere. May this love find me.
From HT Brunch, July 18, 2026
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