Kristen and Rich were set up by their mutual friend Jordan. Rich knew of this set up for weeks, while Kristen was only made aware a couple hours before their meeting. Jordan thought the two would make a good match because they both talk a lot.

In fact, Kristen was supposed to go on a date that night, but it was canceled on her, so she decided to go out with Jordan and her work friend, Rich, and his friends instead.

The group met up at Carrie Nation in Boston. The two clicked immediately. Kristen expressed interest in becoming Rich's new roommate once she moved back to Massachusetts; however, Rich had no interest in Kristen being his roommate and asked for her number instead so the two could go on a date later in the week.

During the week, Rich tried to reach out to Kristen and didn't hear a thing. Kristen had blocked Rich, but had no idea, and had wondered why Rich hadn't reached out to her.

Eventually, Kristen realized Rich was blocked in her phone, unblocked him, and the two set up their first date on the 21st night of September.

Their first date was the best first (last) date Kristen ever had... so much so, that nine months later, she drove up the coast and moved back to Massachusetts to start her new life with Rich.