Kayla and Hugh met in April of 2018 as most millennials those days did... on a dating app. After matching on The League, they had their first date on the rooftop of one of Arlington's finest establishments, Whitlow's on Wilson. On their second date, Hugh took Kayla to a cool speakeasy in Georgetown where he had a coupon for a free drink but decided not to use it to impress her.

In 2021 they moved to Boston when Kayla started graduate school. They now live together in Seattle where they enjoy golfing, hiking, and going out to eat. Hugh still has not used his free drink coupon at the Georgetown speakeasy.