Poppin' the question
My favorite proposal moments in honor of Ben and Leslie
Hey everyone! Sorry that you’ve been hearing from me a bit more sporadically than usual — it’s been a crazy few weeks. I just moved apartments rather last minute, I’ve been skiing, I’m about to head to Mexico City for a wedding, and I have quite a lot of travel coming up in March, along with my Second Annual Birthday Tahoe weekend. It’s so much fun, I’m exhausted, I’m having the time of my life! But have no fear — I’ll still be here every week or so with our regularly scheduled programming.
Thank god, because it’s a biiiiiiig week over here on Park It: Leslie and Ben are engaged!
Part of me wants to say it’s a long time coming, but I actually think their engagement happens … a little fast for TV? They’ve been in the flirt factory since way back in season three, but they broke up at the start of Leslie’s campaign and got back together in season four’s iconic “The Smallest Park.” We’re on season five, episode five this week, so that’s under a season to go from DTR to engaged. It’s no April and Andy timeline, but it’s accelerated.
But as the old romantics say, “when you know, you know!” Ben really knows. He gets a job offer from our old pal Jen Barkley to work on another campaign, this time out of Florida. Back in Pawnee, Leslie’s just put down a deposit on a house for her and Ben. She’s understandably disappointed when Ben breaks the news, but is supportive of his career, as always. Later, when Jen gives Ben the ominous advice to “think about his future” (meaning, she wants him to take the job), he interprets that differently. He hops on a plane from Florida back to Pawnee, intercepting Leslie right as she’s putting their house back on the market. She finds him on one knee, in a suit, biting back tears and holding the largest ring box I’ve ever seen in his hands. (The first time I saw this ep I thought it was a bracelet and we were getting punk’d).
Ben’s proposal to Leslie is perfect. It’s TV writing genius, an excellent celebration of their love story thus far. How fitting that I watched this episode right in time for Valentine’s Day! So this week on Park It, I want to celebrate some of my other favorite iconic proposals from movies and TV:
I’d be remiss to not mention THEEEEEEE Proposal. I recently rewatched the Sandra Bullock and Ryan Reynolds classic, and every minute of it holds up. It’s kind of an elevated Hallmark movie when you think about it. Big city publishing exec with a chip on her shoulder takes a trip back home with a country boy who’s been gone too long, but has duties to take over his family business. One thing leads to another and dot dot dot. Whenever I think of the actual proposal scene from this movie, I think of two things: Sandra on two knees outside the immigration office proposing to Ryan, and Ryan at the end saying “marry me, Margaret. Because I’d like to date you” while the whole office looks on. So good. Also hello baby Malin Ackerman and rip Betty White.
The scene from Set It Up with the blonde roommate and her very generic-looking boyfriend. He proposes in her tiny apartment bedroom, claiming he has to “get a glass of water” so he can sneak out of the living room to … set it up (sorry). I think this is a semi-psychotic move. Imagine you’ve just gotten home, peeled your shoes off after a long day, and someone drops to a knee on your Wayfair rug. AFTER you just had the most romantic dinner ever. Bit of a crazy proposal, but I’m giving it props because it’s the catalyst for some major events of the rest of the movie. Namely, the rooftop engagement party scene where Zoey Deutch and Glen Powell have big sparks fly. And I really love this movie.
The Grey’s Anatomy elevator scene where Derek proposes to Meredith. Look, neither Meredith nor Derek are in my Mount Rushmore of favorite characters, but after my recent Grey’s rewatch, I was reminded of just how insane their chemistry is. I looooved Patrick Dempsey when he was prime McDreamy mode (to this day, my friend Lane and I still have each others’ phone contacts saved as “McDreamy” and “McSteamy”). The moment when the elevator doors ding open and Derek’s standing there, clean shaven, with all of his brain scans hanging around him from their surgical trial … and then he says, “I’m not gonna get down on one knee. I’m not gonna ask a question. I love you, Meredith Grey, and I wanna spend the rest of my life with you.” I MEAN this is iconic TV people!!!
Sweet Home Alabama. I love this movie so much! I love Patrick Dempsey as the other guy, I love their thick Southern accents, I love the town fair scene when Reese is wearing a really excellent joutfit (the modern rebrand of the Canadian Tuxedo). And I love the scene at the end when Reese chases Jake onto the beach in the middle of the thunderstorm to re-propose to him. They’re already married, it’s a long story, but it’s peak early 2000s rom-com energy.
Patrick’s mid-hike proposal to David in Schitt’s Creek. This moment’s actually a bit of a Ben and Leslie homage. David’s turned away, complaining about the hike, and when he turns back around Patrick’s down on one knee. We all know I’m a sucker for a sappy sweet sitcom moment, so Patrick’s speech about how he used to hike up there to make sense of his feelings for David got me real real good. And I can’t even think about Schitt’s Creek without thinking about Catherine O’Hara!!!
In honor of Gal/Valentine’s Days, I’ll just say it: I love watching love on the big and small screens! I love all of these stories and most are deeply imprinted into my brain — but I love Ben and Leslie the most. Let’s get these fools married.






