It all started in August 2022 when Annie was hosting her college best friend, Jen, for a girls’ weekend. On that Saturday night, Jen organized a dinner with some of her high school friends—one of them being Houston, who had recently moved to Portland. Annie and Houston found themselves seated across from each other, but the conversation didn’t really spark until their separate orders of Hendrick's & Tonics arrived. The cheers of those Hendrick's & Tonics turned out to be the beginning of much more than just a fun evening. What followed was a late night of bar hopping, tequila espresso martinis, and a competitive game of pool, along with the start of a connection between Annie and Houston that neither of them could ignore. In the months that followed, Houston did what any romantic would do—he sent a text to DTR (yes, for those also wondering Annie had to Google, it means 'Define The Relationship'). The two spent time meeting each other’s families and friends, traveling together, and quickly realized they made the perfect team. By November 2023, they were roommates, and their first big adventure as a couple was tackling an office flip. Less than a year later, they adopted their adorable (and sometimes mischievous) puppy, Sully, who quickly became both their source of joy (depends who you ask) and their perfect scapegoat... In January 2025, what Annie thought was just another routine dog training session in the park turned out to be the most unexpected surprise—Houston’s proposal, marking the next chapter of their beautiful journey together.