The year was 2015. Al and Mollie were both living in the Lakeview neighborhood of Chicago a few years after college and had mutual friends that wanted them to meet (shout out to Biz & Reebz). Al and Mollie eventually met up at a very cool beer café, Beermiscuous, for a first “date” – Mollie definitely thought it was a date but Al thought it was just a casual friend hang. Still up for debate, but worth noting that Al quickly offered to pay for the first round of drinks. Anyway, one beer turned into a few and the conversation flowed just as easily. Instead of parting ways at what would seem like a normal time, they instead ventured to a cozy martini bar to meet up with one of Al’s friends. Soon, Mollie realized that she left her credit card back at the beer café (classic) but more plans had already been made to grab dinner at Hamburger Mary’s across the street. Full of beer and burgers they thought, “Why stop now?” They were on a roll. They stopped to grab Mollie’s credit card and then bounced to a bar in the heart of Boystown, DS Tequila, that would soon become one of their favorites. After watching some late-night March Madness, they made their way back to Al’s apartment to – you guessed it – watch Jeopardy. After possibly the longest “maybe date” on record, the rest is, as they say, history.

The year was 2023. If it was up to Al, the year probably would have been 2016. With a running “joke” that Mollie was going to have to be the one to propose, she started thinking of plans for a fun, and mostly surprise, engagement trip. Knowing that Al is a huge fan off all things winter and Christmas, Mollie found the perfect place: a historic hotel in Banff, Canada that literally turned into a Christmas castle during December. Bougie? Hell ya. On the first morning of their trip, the two ventured down to Bow Falls through a wintery forest after it had just snowed (you can’t make this stuff up!!). It was beautiful and quiet, except for the garbage truck that drove awkwardly close during Mollie’s proposal, but soon the engagement was official. The rest of the weekend was spent enjoying Banff, the castle, being engaged, and drinking a lot of gin & tonics. See the “Gallery” page for lots of photo evidence.