You never know who you will meet at a Shakespearean themed Luke Rose pool party! John was conversing with friends from high school, when Cari arrived and noticed her former college roommate in the group. Daniela introduced them and they talked all night. After a few drinks and a few swan dives into the pool, John asked for Cari's number. Two days later, he asked her on a date!
The date was set for Michelangelo's Restaurant in Little Italy (the same restaurant where Cari's cousin Carla was proposed to months prior - John had no clue). After receiving a call from John at quarter to five citing a potential work emergency, Cari was concerned she was going to be stood up. However, John put out the fire to make sure he was on time for their date. He arrived with flowers - to Cari's surprise - and she had to scramble to find a vase and figure out how to unlock the rarely used front door. They closed down the restaurant after talking for four hours. With not a gelateria or bakery open on Murray Hill for dessert, they opted for Jerry's on Euclid Ave in Wickliffe.
Planning on spending the entire Fourth of July holiday together, John asked Cari to pick a spot for a picnic. They went to Sims Park on Lakeshore Blvd in Euclid and while enjoying wraps, fruit, and famous Reagan Bark John asked Cari what she "thought" about being his girlfriend. She shared her "thoughts" with him and he asked, "so is that a yes?" To which she responded, "well you just asked for my thoughts..." He then asked, and she said yes, and the two enjoyed the rest of the day, watching Julie and Julia, and heading Downtown that night for fireworks on the lake.
After picking up Cari at the airport at 11:40 (with flowers of course) after a weekend getaway to Texas with her girlfriends, John and Cari had a two hour long discussion about how they missed each other. Feeling a sense that Cari had something on her heart to share, John asked and she said "I think maybe I love you." To which John (coming from a sales background) asked "what can we do to make the think and maybe to for sure? Because I know I love you." To which she responded "I love you too."
After Katie (Cari's roomate) made Cari late to a morning women's retreat to make sure her nails were done, she was skeptical. John asked Cari to meet him in the adoration chapel at St. Francis of Assisi Parish before the 4:30 Vigil Mass. There, in front of the Blessed Sacrament, John proposed and Cari accepted. The first thing they did as an engaged couple was celebrate the Mass. Following Mass, John surprised Cari with friends and family at a house party she thought was only celebrating her birthday.