Even though Kenny and Kaitlynn worked just two blocks away from each other in Boston's Back Bay district, they had never met before. And considering Kaitlynn's weird inclination for book stores and Kenny's preference towards sports bars, they were unlikely to ever cross paths in "real life." Thank god for the internet, amirite? Downloading Bumble was probably the best thing the two have ever done. And it was a match at first swipe. Kaitlynn and Kenny met at a bar in Fenway in 2017 and, within just 20 minutes, Kaitlynn knew she had met "the one." Though the beer probably helped the matter. After countless jazzy dinner dates, Netflix binge shows, and a precariously placed taco festival under an underpass, Kenny and Kaitlynn were as inseparable as they come. In June 2021, Kenny made it official by popping down on one knee in the seaport district of Boston and asking Kaitlynn to be his wife. Kaitlynn isn't sure she "officially" said yes. There were too many squeals of excitement for onlookers to confirm verbal agreement on her part. The jury is still out, but the party is very much on.