It was the summer of 2017. Katie spotted Bailey on one of everyone's favorite lil' dating sites and felt smitten pretty immediately. She sent Bailey a message and waited for a response. And then waited some more. And then a little more after that. Finally, after over a month of silence, Bailey responded. Turned out she'd been pretty busy starting a new job. Totally understandable. After a little back and forth, Katie asked if Bailey wanted to get coffee and keep talking. Bailey said she'd love to, but there was one little problem: she was in D.C. for an internship, and she wouldn't be back until mid-August. The coffee date would have to wait. Bailey and Katie talked constantly over the following weeks. The time they couldn't spend in person in July was used to plan things they could do together once they were back home. Only a few weeks after they'd started talking, the Mcelroy brothers, a podcast favorite for both Katie and Bailey, announced they were coming to Minneapolis. Just like that, they'd planned a date for November before they'd even met in person. Bailey stopped at her hometown in Ohio briefly before coming back to the Twin Cities. She spent her first days back in Minnesota moving into a new apartment with the help of her parents, and Katie had to fight herself back from offering to help unpack in a bid to see Bailey before their first date. They finally had their date on August 14th, 2017. They ran around the Minneapolis Sculpture Garden and ended the evening with dinner at French Meadow, now a Twyman-Metzger staple. Katie was immediately charmed by Bailey's laugh, and Bailey was struck by how easy it was to talk with Katie. It looked like maybe their relationship would fare well enough to get them to that November live show after all.
For Katie and Bailey, the question wasn't so much if they would get married but rather how they would get there. Most popular proposal stories feature a dashing young man dropping to one knee and a charmingly teary-eyed young woman saying yes. For obvious reasons, that script wouldn't quite fit, so they had to create their own. They knew a few things. For starters, Katie likes surprises, Bailey not so much. Second, they both wanted rings. None of this waiting-till-the-wedding-day nonsense. While Bailey would be the one actually proposing, Katie knew she'd need a ring stashed away for when the moment came. Both began their scheming privately. Bailey knew that she wanted the proposal to take place at home. She and Katie are both homebodies and weren't interested in anything showy. After tossing around a few ideas, Bailey decided to propose with good ol' breakfast in bed. Katie and Bailey had just moved into their new apartment, and Katie was fixated on the idea of making pancakes in their new home. Bailey dodged Katie's many suggestions for pancake breakfast, pancake dinner, pancake everything. Instead, Bailey bought secret pancake mix, a tiny bottle of syrup, and two tiny bottles of champagne which were then carefully stashed away in her sock drawer. The morning of September 9th, Bailey woke up before Katie (as usual) and snuck off to the kitchen. Never has anyone made pancakes with such anxiety. Bailey was so afraid of waking Katie up, it took an entire hour to finish making breakfast. Fortunately, sleeping is one of Katie's many talents. She didn't wake up until Bailey came into the room with a breakfast tray, a little ring box off to the side. Bailey stood at the foot of the bed, tray in hand, and half-shouted, "HEY KATIE." Katie rolled in bed and hmphed, not paying much attention until Bailey asked, "Will you marry me?" Not one for charming teary-eyes, Katie's first reaction was to shoot up in bed and yell, "WHAT ARE YOU DOING?" It all worked out nicely.