On The Bachelor, goofy girls like Gabby Windey don’t always finish last, but they never finish first.
It’s a bummer, because Gabby is the rare Bachelor contestant who is legitimately funny. In the first few minutes of her hiking-themed hometown date with Clayton, she told him that he would have to “cut down trees and fight bears” to meet her family, joked about how big an engagement ring needed to be to fit over her winter gloves, and (playfully) threatened to kill him atop a scenic overlook. That all came after a season filled with classic Gabby moments like double-fisting bottles of champagne and rolling around on a city sidewalk with a dog.
She’s not just a little silly, like the kind of girl who gets called “random” for having the slightest hint of a personality. No, Gabby is a lateral-thinking, free-associating comic force who’s easily the most entertaining person to watch this season. In fact, it hasn’t been since taxidermy enthusiast Kendall Long’s appearance on Arie Luyendyk’s season that someone in the Bachelor franchise has literally made me laugh out loud.
Which is why it’s a shame that Gabby might not last much longer. I’m not spoiled on the season, but it’s pretty clear to me from all the intimate whispering and horny Jiu-Jitsu that Clayton is more smitten with Rachel and Susie than he is with Gabby.
If Gabby does manage to make it into the final two, she would be forging new ground for genuinely funny contestants in Bachelor Nation. People like Gabby simply don’t make the final two. In fact, third place seems to be something of a ceiling for Bachelor contestants who showcase a strong sense of humor on the show: Kendall placed third on Arie’s season, getting eliminated after a particularly macabre hometown date in which she and the Bachelor took a pair of taxidermied rats on a mock Parisian vacation. (The recently published guidebook How to Win the Bachelor called Kendall “the most successful player to employ the Weirdo archetype.”)
Try as they might, so-called “Weirdos” just can’t seem to make it to the finale. Case in point: Kaitlyn Bristowe, who in my opinion was the most amusing Bachelorette in history, was cast as the lead of her own season after finishing — you guessed it — third on The Bachelor. She notably introduced herself to farmer Chris Soules with an off-color invitation to “plow [her] field.” Gabby followed in Bristowe’s footsteps this season with a limo entrance pun of her own about sitting on Clayton’s face, which only makes me more concerned that she’ll end up exiting the season at the same time as her predecessor and inspiration.
Indeed, it’s at this point in any given Bachelor season that the lead typically begins narrowing down his options to sweeter, more predictable personality types. Arie sent Kendall home after their outré rat date and ultimately ended up with the very quiet Lauren Burnham after initially choosing the other girl-next-door type, Becca Kufrin. Chris similarly gave Kaitlyn the boot and ended up proposing to the outgoing but much less hilarious Whitney Bischoff. I don’t mean this as an insult to either Lauren or Whitney, both of whom I like. But I do find it interesting that the traditional guys who tend to get cast as the Bachelor opt in the end for women who don’t seem too eccentric. A zany girl still seems to threaten many a man looking for a wife.
You could watch that process play out on Clayton’s face in real time during Monday night’s episode. When Gabby made a joke about Clayton having furry hobbit feet as he was putting on his hiking shoes, the Bachelor said, “What?” with a look of genuine befuddlement that almost seemed to cross over into terror. “The next word that comes out of her mouth is always a wild card,” he told the cameras, inadvertently revealing that Gabby may be one of the first truly offbeat people he’s ever met. (Honestly, the reference was not that weird!)
Clayton seems jovial and goodhearted, but if you’re funny and you value humor in your social relationships, a hobbit joke is par for the course, not cause for shock. I do have to say, however, that Clayton’s inebriated TikTok pizza review was hysterical. Credit where credit is due.
Setting the comic potential of that drunken video aside, Clayton is going to be better off in the long run with someone who isn’t “a lovable dingbat,” as Gabby’s grandpa memorably called her. He needs someone who makes him happy without giving him deer-in-headlights eyes or embarrassing him in public.
But maybe that’s for the best, because it would free up Gabby to become the next Bachelorette. While recent Bachelorettes have been able to crack the occasional joke, none since Kaitlyn have truly captured that extremely entertaining oddball energy. Imagine what Gabby could do — and how many bottles of champagne she could try to drink simultaneously — with an entire season of airtime.
Maybe that would be a first-place finish after all.