2019
Jake gets invited to a party with his cousin Sydney’s college friend group. While there, he notices a cute girl—Molly. She’s caught up in talking with her friends, so he decides not to strike up a conversation. A few months later, fate (or the Hinge algorithm) gives them another chance. They match, chat, and… well, let’s just say the conversation doesn’t lead to a date. Some (Jake) may call it ghosting, others (Molly) may say the conversation fizzled out. Regardless, no date happened, and the two went their separate ways for the next two years.
July 2021
Molly is at a Cubs game with her besties, Sydney, Jordan, and Sara. She mentions that she’s ready to start dating again following the pandemic, so Sydney throws out the idea that she should go out with her cousin, Jake. Molly agrees and Sydney sends Jake a text with the proposal. Given the Hinge experience, Jake is more than a bit skeptical, but he decides to play along and reaches out. Molly, however, is busy for the next week. She suggests squeezing something in on a Monday night—the same Monday Jake starts a new job. They agree to meet at J9 Wine Bar in Lincoln Park, a place that will become their anniversary tradition (spoiler alert).
July 12, 2021
Jake is going through onboarding at his new company when he gets a text from Molly, “Hey, I just want you to know I’m a bit sick, but I can still go if you’re comfortable.” Jake reasonably assumes that Molly is trying to get out of the date, but he doesn’t give her the satisfaction. Jake promptly shows up to J9 at the scheduled time. Molly texts him that she’s running late and is looking for parking. Jake is a bit frustrated, nervously ripping up the napkin holding his water glass. Molly does eventually arrive and the date begins. Jake orders a hard cider (not his usual), and Molly orders a cocktail that “looks good” but that she doesn’t like and doesn’t drink (this is very classic). Standard small talk and icebreakers occur and the date is average… mid as the kids may say. But things shift when they open up about more personal topics. Some may say sparks began to fly. The conversation flows, Molly gives Jake a ride home, and they agree to meet again the next weekend. Less than a month later, they make it official—because when you know, you know.
2021 - 2023
Travel quickly becomes a cornerstone of their relationship. Five months in, they take their first trip together to Cancun, where something in the piña coladas seals the deal—they fall in love. Since then, they’ve explored Portugal, Napa, Montreal, New England, Florida, and the Wild West. That last trip featured 20+ hours in the car belting show tunes, Pentatonix, and Demi Lovato. While some may view that as cruel and unusual punishment, Molly and Jake see it as the perfect trip. Both have pursued MBAs during their relationship—Molly recently graduated from Booth, while Jake is more than halfway through Kellogg. The debate over which school is superior remains unresolved. They buy a home together in fall 2023 and take the plunge of cohabitation.
April 27, 2024
Jake decides in early 2024 that he is going to propose some time in the early spring. Though Jake tells Molly the first (and only) time he goes ring shopping with his parents, she doesn’t know that he buys the ring that day. Jake and his family have Molly completely convinced that there’s no engagement ring because a pear diamond is hard to find. To maximize surprise, Jake proposes at home. The day of, Molly is stuck at what feels to Jake like the longest lunch ever. At home, Jake sets up a romantic display—candles and roses—and perfectly balances his phone in a mug to capture the big moment. Molly says yes, of course. But after the proposal, Jake realizes he fumbled capturing the moment because he kept anxiously picking up his phone to track Molly on her walk home. The footage is completely useless as it’s facing a wall, and because Molly blacked out during the proposal, she is convinced Jake didn’t get down on one knee (he did). Oh well—at least the memory is perfect.
July 2025
We’ve had a blast merging our families as we approach our wedding and can’t wait to celebrate with all our closest friends and family. Thank you so much to everyone for being part of our love story so far, and we hope you all will continue to be part of it for years and decades to come!