Kelsey and Ryan met in June of 2015. Both were hand selected to be a part of a pilot team at Groupon. During the pilot team kick off, they both learned that one another were from New Jersey and were equally as chatty. Both were under the impression that the other was in a relationship, so neither of them made any move to take anything further. A few months later, without Ryan's knowledge, his boss approached Kelsey and asked what she thought of him and jokingly told her, "go have a bowl of pasta with the guy, or a piece of pie with the guy." Kelsey said she would love to, but wanted it to happen organically. Ryan's boss knew that millennials weren't good at making things happen organically, and immediately called Ryan while he was sitting next to Kelsey to tell Ryan that she was indeed interested. After two Groupon team outings and a push from their coworkers who knew they were meant to be, they finally went on their first date. They spent 9 hours together walking around Chicago and talking each other's ears off. The rest was history.

Kelsey and Ryan got engaged on May 17, 2018 in Chicago. Ryan's plan was simple – make up a sales contest, where he worked at Groupon, and tell Kelsey the award was a "Staycation" in Chicago for a weekend. Sure enough, Ryan “won” this contest, and ensured that Kelsey would be available that weekend. On May 15, Kelsey told Ryan about a house in Indy she thought was their forever home. They had been looking for months, and she knew that this house was going to move fast, and they needed to act quickly. On Thursday night May 16, after a Facetime call with Ryan, who was in Chicago, they decided they were going to put an offer in on the house. On Friday, Ryan decided to write a letter to the sellers explaining to the vision for the home, what excited them about it, and let them know they’d be handing it off to newlyweds. Friday night, around 5pm, Kelsey met Ryan in Chicago on a riverboat - Kelsey thought his boss would be joining then. Turns out, it was just the two of them, and 10 minutes into the boat ride, Ryan asked Kelsey to turn around to look at the skyline. When she turned back, Ryan was right there on bended knee asking her to be his wife. The next day was full of surprises! Ryan booked a mani/pedi for Kelsey, and then walked to brunch. As soon as they walked in, they were greeted by Kelsey's family from Indiana, and Ryan's family who flew out from NJ! From there, they met more friends at City Winery along the water, followed by a party at a local bar with 40 close friends to the happy couple. Around 5pm that night, Kelsey received a text from the realtor asking if she could talk – the sellers wanted to speak to them. Anxiously, Ryan, Kelsey, and her mom step out of the party to take the call. After congratulating them on their engagement, the sellers said they were very moved by the letter, and wanted to congratulate Ryan and Kelsey on one more thing – becoming homeowners. It was a whirlwind of a weekend, and one to never, ever, forget.