5.22.2027

Bobby and Liz went ring shopping in February and Bobby went back and bought the ring a month later. He waited until they were going to visit his sister in Chicago and Bobby slipped the ring into his duffle bag unnoticed. Unfortunately, security tried to ruin the surprise at the airport when Bobby's bag got pulled, but they luckily did not pull the box out. Jenna and Romain's cat Pistache also decided to take the ring box out to play with in the middle of the night. Luckily, Liz still did not notice. Finally, that Saturday, Bobby and Jenna enacted their plan. After convincing Liz to dress nice for the day and explaining that Bobby was wearing a blazer purely as a fashion statement, they went to Lincoln Park to visit the conservatory. Bobby pulled a quick spin move while posing for a picture and proposed to Liz. Immediately after, they went and looked at lions at the zoo and had a lovely Italian dinner.