An aspiring young pilot meets a technical writer on a chance encounter crafted from the sketchpad of three matchmakers, each on a mission to write the lives of two unassuming singles into fated alignment. Ms. Danielle’s and Ms. Dee’s, “Hey, we have this nice girl we want you to meet, you should really give it a shot. It’ll be worth it!” was the complement to Ms. Kim’s, “He’s really cute and he’s a pilot!” The unscripted coaxing of these go-betweens and the brandishing of Ashley’s and Kenny’s best Facebook pictures set the stage for the canvas that was to become. The meeting place: Copper Canyon Grill. She was cautiously optimistic; he was late. To him, she would be his last blind date. Little did he know that he would be hers too. To Ashley, Kenny’s easy humor and good-natured smile were the beginnings of something charming and serendipitous. To Kenny, the moment Ashley ordered a blue moon, he knew that the date would end well. And so it began…

Kenny and Ashley’s romantic milestones are truly a story of firsts. Kenny drove from Delaware to Maryland to accompany Ashley to her first formal event at her new job. This night of decadence would become the catalyst for their first major appearance, and official test of their compatibility, as a blossoming couple. This was also Kenny’s first time being anyone’s date to a formal event. Dressed to the nines, Kenny and Ashley dazzled each other under the classy glow of the lavish party: They danced and deepened their affinity for each other over a banquet-style meal and live entertainment. The sweet success of this milestone spurred Ashley’s first road trip from Maryland to Delaware. She had never driven this far to see someone she was dating, and before Ashley, Kenny had never asked anyone to hold his hand while piloting steep and daring turns at 5000 feet. One short year later, Ashley and Kenny enjoyed their first baecation in New Orleans as a boyfriend and girlfriend. By day, they took a lovers stroll down Canal street, drank in the sights and hurricanes on Bourbon street, devoured history—and gator dogs—at Studio B, and cozied up to the sounds—and each other—at a jazz lounge by night. Of course, there was bar hopping too, and lots of opportunities for Kenny to play photographer to Ashley’s keen eye for interesting doorscapes. With Kenny’s erratic work schedule, this three-day vacation was the most time both of them had spent in each other’s company and shared space. This dynamic set the tone for the first of many staycations.

Four years and one move in later, Kenny, now a commercial pilot, knew that he was going to be away on another work trip the week of February 14th. He knew that he was going to miss Valentine’s Day with his sweetheart. But, he also knew that he was going to propose when he got back. In fact, Kenny knew that he had wanted to pop the question for a while; he just hadn’t settled on the when. Six months earlier during his family reunion trip to Ohio, Kenny happened to be in Macy’s with his cousins when he got the idea to look at rings. The jeweler not only showed him some pieces but gladly told him how to get extra discounts on rings—and he pocketed the advice immediately. Kenny got the ring about a month before he proposed. He narrowed it down to two rings: A tear-drop diamond solitaire and the ring that was to become Ashley’s forever. The decision was a tough one, but Kenny ultimately picked the ring based off what he knows Ashley likes—clean and simple. And then it happened. He looked up from his phone, looked over at Ashley, and used the smile that suddenly washed over his face to confirm his order. Kenny purchased the ring in front of Ashley as he beamed at her from across their living room. She had no idea (until now). He texted his mom a photo of the ring, and would share the news with Ms. Kim, Nicol and Na’eem soon after.

On Valentine’s Day, Kenny sent Ashley a dozen red roses in his absence. When Ashley received the bouquet, there was a memento nested inside the vase among the stems: a picture of a memory that the two had created at the National Harbor. One week later, Kenny planned a makeup dinner that would end up changing the course of both of their lives. Kenny made Ashley believe that this make-up dinner date at Lauriol Plaza would proceed like all the other dinner dates they’ve had: They would eat, hang out, then go bar hopping. They started the night with frozen margaritas at the bar before being seated at the table where it would all go down. Kenny couldn’t stop thinking about how he was going to orchestrate the proposal. At the very least, he knew that he wanted to record Ashley’s reaction on his phone. Kenny’s plan remained above suspicion as Ashley ate (she was busy talking about their after-dinner plans). Moments before the bill came, Ashley went to the bathroom. That’s when Kenny knew it was now or never. He had just enough time to ask the nice couple across from him to document the moment and check on the ring one last time. When Ashley returned to her seat and resumed her conversation, Kenny interrupted her, “I can’t wait anymore…” Confused, Ashley responded, “Wait for what? What are you talking about?” That’s when Kenny got down on one knee. Filling his moment’s breath with the joy of truly catching her off-guard, he said, “Will you marry me?” He looked up at her intently, reading the simultaneous shock and elation in her eyes. “Of course!” Without hesitation, Ashley accepted and the entire restaurant erupted into cheerful applause. Ashley’s first call went to Nicol and Na’eem. Kenny’s first call went to his mom. The next morning, Ashley twiddled her feet with excitement, reveling in her new enfianced status and Kenny couldn’t have been more happy for her.

From chance set up to amiable first encounter to amorous pairing to happily ever after, let us pledge our best wishes to the happy couple below!