According to Eileen: Although you would think since we went to the same high school, meeting at Prom means we met at Ignatius, however it would not happen for many years later. In April 2016, Eileen's friends were throwing a Prom party as an excuse to wear our prom dresses another time. Naturally, Eileen's friend from Ignatius, Kaitlin was very excited to recreate pictures from our actual prom days. Kaitlin was dating Connor at the time who was one of Sam's really good friends, also from high school. Connor brought Sam to the party, hoping to set up his friend. After the prom photos, everyone met at Alive One for the celebration. After Prom Queen was announced, Eileen was disappointed for not winning but Sam was there to sweep her off her feet. They danced the night away and ended up at Bottled Blonde. Since Eileen was in her prom dress, people at Bottled Blonde thought it was a wedding dress and were congratulating the couple on getting married. Sam and Eileen went along with it and pretended they just got married, mostly for the free drinks. Little did they know they actually would be getting married 4 years later. According to Sam: Eileen and Sam met at prom. They both went to St. Ignatius so you would think this was high school prom, but it was actually at a prom party Eileen's friends threw after graduating college to both get another wear out of their dresses and prove they could still fit into them. They hit it off at the party and although Eileen was devastated to barely miss out on winning Prom Queen (for the record the vote was rigged), they had a blast and spent the rest of the night accepting free drinks from people who thought they had gotten married and wanted to spend their wedding night at faux-nightclubs in River North.
According to Eileen: After the magical prom night, Sam was dying to take Eileen on a date. She is a very busy lady and was traveling for the next few weekends, U of I graduation, the Kentucky derby, and a work trip to present her thesis. Sam was beginning to lose hope but then he was able to score some tickets to the Beyonce concert and he knew it would be hard for her to say no to this. He picked her up like a gentleman and they went to Parlor Pizza for dinner before the concert. They arrived just as Beyonce was about to perform. The seats and show were both incredible. It was definitely a once in a lifetime experience. According to Sam: After a magical prom night, it took a while for them to see each other again. Eileen was always "busy" or "working" or "out of town", but Sam knew the one thing a lady couldn't turn down: Beyonce tickets. They had an incredible night going to Parlor Pizza and then seeing Beyonce at Soldier Field. It's definitely a night neither one of them will ever forget. The only thing that could have made the night better is if they would have taken a selfie together at the concert, something that still haunts Sam to this day.
According to Eileen: July 16,2019- It starts off as a nice little Tuesday. Eileen and Sam took off work and went to Wisconsin to pick up their brand new Australian Labradoodle, Stewie. It just so happened to also be their anniversary. They decided to go to the Aviary since Sam had one of their cookbooks and they had been dying to go for awhile. When they walked in the restaurant it turns out they were seated at the private table in the kitchen. The got the full experience of pairing the drinks with the delicious food. When they got home, Eileen went to take Stewie out of his crate and found a white bandanna around his neck that said "Will you marry me?" She turned around and Sam was down on one knee with a gorgeous ring. He asked her to marry him through tears of joy and she exclaimed YES! She was completely surprised, just like she wanted! According to Sam: Eileen and Sam had been on a wait list for a dog for almost a year when their turn was finally up. They were all set to pick up Stewie in Wisconsin on July 16th, which was already a special day since they started dating on the 16th of August and go out to dinner on that day every month. Sam had grown up around dogs his whole life, but Eileen never had one and was a little skeptical. "Are you going to love Stewie more than me?", Eileen asked countless times. There was only one surefire way to ensure Eileen would be converted into a dog person: involve Stewie in the proposal. While Eileen and Sam went to their monthly anniversary dinner, Sam's sisters helped prepare Stewie for his big moment. When they returned from dinner, Eileen found Stewie in his crate with a "will you marry me?" bandanna and when she turned around Sam was on one knee with a ring.