In the summer of 2020, masks and all, Greg greeted Kelsey after 12pm mass at St. Paul's Roman Catholic Church. He chased her down and welcomed her to church, though she politely said she had been going there for 3 years. Their paths did not cross again until April 2021 when they ran into each other again. Greg had been looking for "the girl with the green purse" at every mass he attended, and Kelsey could not remember Greg's name but hoped to run into him again. This time, they walked and talked in the rain and made plans to see each other later that week. Their first date (and first time seeing each other without masks!) was April 16, 2021 at Hawthorne's. They have been laughing and supporting each other ever since.

After a wonderful New Year's Eve dinner at Dante and Luigi's downstairs, Greg and Kelsey enjoyed a movie (Home Alone 2) before Kelsey started falling asleep on the couch at 11pm. Kelsey didn't care about staying up to ring in the New Year, but Greg insisted that if they go to bed, they had to be up at 12am to see the fireworks from their window. Kelsey wasn't happy, and secretly hoped Greg wouldn't set his alarm to get up. As promised, Greg's alarm went off at 11:55pm and Kelsey reluctantly got up to watch the fireworks and have a glass of champagne. In PJs and with bedheads, in the first minutes of 2024, Greg asked Kelsey to marry him.