In the vast digital jungle of 2022 dating, where swiping was less “finding your soulmate” and more “avoiding people who still use ‘YOLO’,” Jenna stumbled upon Kyle on Hinge. And his standout feature? Not a gym selfie or a fake candid, but a proud-as-a-peacock pose with a pineapple. “Well, that’s different,” Jenna mused, swiping right because, honestly, she had to know more. Fast forward to their first meet-up at Bastion. They both knew the place and expected a chill evening, but fate had other plans: Hip Hop Karaoke night. “Because nothing says ‘first date’ like strangers butchering ’90s rap,” Kyle joked. Deciding to save their eardrums, they ducked into a quieter coffee shop nearby. Over some caffeine, Jenna, with a mischievous glint in her eye, threw down a chess challenge. Kyle, ever the optimist, thought, “How hard could it be?” Spoiler: pretty hard. Turns out, Jenna was a chess ninja, and Kyle was, well, not. From a tropical fruit mystery to a surprise karaoke backdrop and a humbling game of chess, Jenna and Kyle’s story started off with all the right kinds of unexpected. Just goes to show, sometimes the best stories start with the most random of opening lines – or in this case, pineapples.

Jenna has always been a die-hard Jonas Brothers fan. Over 20 concerts and counting, her dedication to the trio is next level. So, when Kyle was brainstorming the ultimate proposal setting, it hit him: a Jonas Brothers concert! Two months before the big day, he shot his shot with Team Jonas. Days turned into weeks, and just as Kyle was about to lose hope, a “YES!” from Team Jonas popped into his inbox, a mere week before the concert. Even better? The Jonas Brothers themselves were game to be part of the proposal magic. However, with all the planning, Kyle had overlooked one tiny detail: the ring. Drawing from their heart-to-heart chats about Jenna’s dream ring, he set out on a mission and, in no time, found the one that was unmistakably Jenna. Concert night rolled around, and Jenna was just gearing up for another epic JoBros performance. Little did she know, Kyle had some backstage tricks up his sleeve. When they arrived at the concert venue, they were "randomly upgraded" to the B Stage to be featured for the kiss cam. This, of course, was all part of Kyle's plan, coordinated with Team Jonas. Joe Jonas himself was even behind the kiss camera! Now, here’s the kicker: Jenna had always made it crystal clear that public proposals were a no-go. But as “Love Her” played, Kyle thought, “Well, if you’re going to go public, might as well do it in front of 30,000 people, right?” And with that, amidst a sea of 30,000 cheering fans, he dropped to one knee. Jenna, a mix of shock, joy, and probably thinking, “I could kill him, I told him no public proposals!”, couldn’t help but laugh and say “YES!” What started as a night of music turned into an engagement party for 30,000. It was a blend of love, music, surprise, and a good dose of Jonas Brothers flair. And let’s be honest, who could say no with the Jonas Brothers as your wingmen?