It was a beautiful Thursday evening. Tom had just wrapped up golf league and, feeling confident after approximately three decent shots all night, headed to Riverfront Grill. Meanwhile, Alyssa was out grabbing dinner with her sister, Alysha. Tom wandered over to introduce himself. Alyssa responded with a two-handed handshake that was apparently so powerful it short-circuited Tom’s ability to think rationally. From that moment on, he was hooked. The rest of the evening was spent drinking Fireball, laughing, and making what seemed like excellent decisions at the time. After that night, Tom and Alyssa texted occasionally. By “texted occasionally,” we mean Tom would send a message and Alyssa would thoughtfully place it in her “I’ll deal with this later” folder for several weeks at a time. Despite being repeatedly left on read, Tom remained persistent. Against all odds, on December 26th of that year, Alyssa finally agreed to go on their first “non-date,” which was absolutely not a date… except for all the parts that made it a date.

Tom and Alyssa were getting ready to head out to dinner to celebrate the anniversary of their very first “non-date” when Tom popped the question. Over the course of the year, there had been no shortage of proposal-worthy opportunities. Between trips to Colorado and Las Vegas, ski weekends, Chicago adventures, Tigers and Lions games, Candlewalk, and countless picture-perfect moments, everyone wondered when Tom would finally pull the trigger. As it turns out, he was playing the long game. Wanting the people who mattered most to be part of the moment, Tom first asked Alyssa’s dad, Alan, for his blessing. He then secretly recruited Rosalie, Samantha, and Bo, giving them advance notice so they could have their cameras ready for the big event. As Tom and Alyssa walked out to the car for their dinner date, Tom jokingly teased Alyssa about having too many anniversaries and said, “Maybe I should just propose right now.” Assuming this was just another one of Tom’s jokes, Alyssa laughed, until she realized he was serious. Then came the repeated, “Wait… are you serious? Are you ACTUALLY serious?” before the reality of the moment finally set in. With family cheering, cameras clicking, and plenty of happy tears and excitement, Alyssa said yes. The celebration didn’t stop there. The newly engaged couple spent the rest of the evening making the rounds through town, stopping at Tom’s mom, Denise’s house, Alyssa’s dad’s house, and calling and visiting close friends to share the exciting news. After a year of keeping everyone guessing, Tom finally picked the perfect moment, and it turned out to be worth the wait!