After two years of dating and living together through a pandemic, I knew Hayley was the one. My initial intention was to propose on our Hawaiian trip that we had scheduled for the summer 2020; however, the COVID travel bans put an end to that idea. Limited by options, I tried to secure a location with a view where our immediate family and friends could participate in the event. My search for the perfect venue ironically led to the rooftop of our apartment building. It was the ideal setting to facilitate a secret proposal with family prior to our small, housewarming party with friends. Seeking help from both families, I decorated the rooftop with a flowered archway and numerous candles. Hayley anticipated that her sister would attend the party, but she was completely unaware that our immediate families would be present on that day. Her sister “arrived early” to our housewarming and convinced Hayley to venture up to the rooftop for a “surprise gift” that I had built for our new apartment. That evening, with the Chicago skyline as our backdrop and our immediate family watching, I proposed to the most amazing woman I have ever known.