Brennen and Jenni met at a mutual friend's Super Bowl party in 2018. Jenni noticed Brennen and later found out that he plays hockey and rides horses. As an avid Washington Capitals fan and equestrian, Jenni was intrigued. Brennen was shy (to say the least), but they had a few conversations throughout the night. The day after the party, when studying for the LSAT with her friend at a Starbucks, Jenni decided to "shoot her shot" and message Brennen on Instagram saying she enjoyed their conversations the night before. After getting cheeky and asking Brennen for his number, they finally went out on a date in September of 2018 after getting to know each other better.

Brennen and Jenni went on vacation to Hawaii in April of 2024. Jenni had asked Brennen if there was anything she needed to prepare for and he told her "no" (spoiler alert, she was misinformed). While there, Jenni and her sister, and maid of honor, Courtney went to the nail salon to get manicures and pedicures, however, due to a pretty bad sunburn on her legs, Jenni refused to sit around for a manicure after she had her sunburn aggravated by the pedicure and Courtney had already finished her manicure. Brennen and Courtney tried to insist, but Jenni was stubborn (because, duh) and still refused. Brennen had planned on proposing on a catamaran ride that was planned for the next day, but postponed because of Jenni's stubbornness. After flying to Kaua'i from Maui, Jenni's mom tried to get her to get a manicure but Jenni, again, declined. Brennen ended up saying "screw it" and proposing on a kayak/hike to a hidden waterfall the next day on Kaua'i. Jenni was shocked and (temporarily) mad when she found out that he had fibbed about her needing to get her nails done before leaving for Hawaii. Safe to say she has now forgiven him.