It was Labor Day of 2020 at my mom’s BBQ when Max, my mom and Chip had a moment alone outside on the deck. I told them that I planned to ask Jess to marry me. It was something I had known I was going to do for a long time at that point, but it was the first time I had meaningfully said it out loud. I knew my next task was asking for Jeff’s permission. It took me weeks to muster up the courage to ask him. I had worked through a plan and timeline in my head and had targeted the operation to take place on New Year’s Eve when our families had planned to be together. It was late-October when I called my future father in-law and stumbled my way into the question. He updated me that he and Karen didn’t plan to be in Florida any more this winter and suggested that they would be in Philly for Thanksgiving a mere 4 weeks later and I do it then. Sounded like I needed to get to work. And quickly. I fortunately was able to view diamonds and secure the hardware rather quickly thanks to good friend Art Jacoby. Now all I needed was a plan. I thought about everything, or at least what felt like it. With both of us being such Philly people and this city meaning so much to us and our relationship, the art museum kept coming back to me as the perfect setting. Keeping it a secret from Jess was going to be the key, and also the most painful part. For a month it was the most exciting thing going on in my life and not only was I not able to share it with the one I share everything with, but I also had to pretend as if everything was status-quo. I know most men who successfully pull this off have shared this experience but man, talk about painful. My mom became my “idea woman” and my brother, best friend and eventual best man became my Chief of Staff. He directed traffic. All communication about the operation had to be vetted by him and he was the only one allowed to communicate with me directly under a specific code word.

Finally, after an excruciating Thanksgiving Eve in LBI where everyone except Jess knew what was going to happen two days later, the day had arrived. I pretended to have to use the bathroom for an hour that morning to call my brother, Mike and Laura to confirm all of the last-minute details and pace around the 2nd floor common area of our apartment complex. Now I just needed to kill 5 hours and come up with an excuse for stopping by the art museum on the way out to my mom’s that evening. So I fabricated that my Uncle Gary and cousin Katie were in town for the day and I told them that we’d stop by to say hi to them and had decided on the art museum as our meeting place. She bought it like a cute dress on sale on Asos. Execution time. “Stay the course”. “Rely on your teammates”. “Trust the Process”. I said in my head over and over again as we left the apartment. Had I remembered the ring? Did she have any idea? Was I acting absurdly weird? I felt blacked out pretty much the whole day. We pulled up to the art museum where I illegally double parked a Mister Softie ice cream truck and, from what I’m told. Promptly dragged her to the top of the stairs in haste. She asked where Gary and Katie were and maybe started to put some of the pieces together. I dropped to one knee, opened the ring box upside down and asked the love of my life to marry me. I don’t know what happened next, but before I knew it we were celebrating with our siblings, and soaked in champagne. The rest will simply be known as “history”.