The first time Jack and Emily met each other was during a virtual interview in the summer of 2018. Emily had already been working for the company for close to a year, and Jack was in the final stages of the offering process. The company thought it'd be a good idea for Emily to speak with Jack to give him a young person's perspective on working at the company and ensure he was the right fit for the role. In the spirit of making a good first impression, Jack was 15 minutes late and clearly unprepared. It was later found out that he and his friends were getting Chick Fil A at the time and it had slipped his mind.

When Jack somehow got the job and showed up on his first day, Emily was the first one there to let him into the office. Jack explained that the day prior he had taken the subway to the office to practice the route. Hearing this, combined with the fact that Jack was overdressed wearing a full suit, Emily couldn't help but think the company hired a complete dork that summer.

After months of working together, Jack and Emily realized they got along very well. To Jack's surprise, Emily had offered to take him out for celebratory drinks to mark the closing of his first deal. She took him to a Mexican restaurant in the East Village that, according to Emily, had some of the strongest margaritas in New York. Emily had mentioned a number of times that the happy hour ended at 7:00pm so when 6:55 rolled around and Emily told to Jack that they had to "slam their drinks" in order to get another before the happy hour ended, he was stunned. From that moment on, Jack was enamored and a secret office romance started not too long after. The rest is history.

Jack and Emily first visited upstate in the Fall of 2021 and fell in love with the area. So Emily was thrilled when they could plan another weekend getaway to the Catskills two years later. Jack saw this as his best opportunity to propose, knowing Emily preferred an intimate setting and had vetoed his jumbotron at a Mets game idea. Jack planned to propose on Saturday night during a candlelit dinner at their cabin. He had everything mapped out in his mind: they would be dressed up, enjoying a delicious dinner and wine by candlelight in their cozy upstate cabin. Then, he would kneel by the dining room table, hold Emily's hand, and express all the reasons he loved her before popping the question at the end of his prepared speech.

However, reality turned out slightly different. While Jack was cooking dinner, he noticed Emily changing into sweatpants, opening a bottle of wine, and settling onto the couch. He knew he would definitely have to adjust his plans when, as he brought the plated dinner out, Emily suggested they eat on the couch while watching TV. Not ideal, but Jack decided he could still make it work. The real twist came when Emily chose to remain lying down on the couch instead of sitting up to eat.

Jack could tell this was as a good a shot as he was going to get and decided to take Emily's hand, and get down on one knee. Despite the fact that he was looking down at her, which was not at all what he had envisioned, he began reciting the words he'd memorized for the proposal which seemed to catch Emily off guard. Like something out of a movie, Emily looked up at Jack and said "Why are you saying all these nice things? What, do you have a ring in your pocket?" To which Jack replied "it's funny you say that". He pulled out the ring and asked Emily if she'd marry him. Emily was stunned and began frantically asking questions - "How long have you had this?? Is this real?? Are you being serious?? Who else knows about this?? Did you already ask my parents??". Jack noticed she technically hadn't said yes yet, which he kindly reminded her of. After building up enough suspense and beginning to tear up, Emily said yes.

The service upstate was poor and the Wi-Fi was borderline unusable, so Emily spent the next 30 minutes or so calling her friends and family from the cabin landline telling them the news. The rest, as they say, is history.