How did this New York boy and Chicago girl find each other? It was New Year's Eve 2012. Kev headed from NYC to Atlantic City for an epic pool party with DJ Pauly D. Meanwhile, Jaclyn, who was visiting her best friend Sabrina in New York, was trying to figure out where to spend the big night. After almost missing their train to Atlantic City, fate somehow brought Jaclyn to the same pool party. Kev spotted a beautiful blonde standing at the bar. Unfortunately, that girl left, and then a few minutes later he noticed Jaclyn. He approached her and asked to buy her a drink. Jaclyn was captivated by his charm and good looks. Unfortunately, she had to cut the night short since Sabrina was having a mini meltdown and wanted to go back to the hotel room. (That is another story for another time) Jac told Kev, "It was great meeting you," and thought she would never see him again. But what happened next may just be the reason you are all coming to Cabo. As soon as Jaclyn got to the room, her phone lit up. It was Kevin. He was geniunely concerned about Sabrina. Wow. This kid was not only tall dark and handsome, he also had the biggest heart... WHAT HAPPENED NEXT? They didn't speak for over 1 year. Why? Jac went back to Chicago and Kev headed back to New York. Life got in the way, but that all changed when Jaclyn decided to move to NY. After living in the city for a few months, she remembered that sweet boy she met in AC. Jac sent him a text asking if he still lived there. Kevin replied, "Who is this?," which was pretty hilarious. They set a date at a Tapas restaurant in the Lower East Side for drinks. Coincidentally, Jaclyn lived above the restaurant and happened to work there (Jaclyn is all about convenience). Kev canceled the first date- as he broke his chin playing soccer. He canceled the second date because of a last minute work trip. Some girls would have given up. But not Jaclyn. Eventually they ended up at Tapeo 29 for their first date. And the rest is history.

It was a rainy night in New York City. The date was Thursday, February 6, 2020. Jaclyn was in town for a Bravo Premiere & Kevin was in town for meetings. At least, that’s what Jaclyn thought. That night, they had plans to meet friends for dinner at TBar (their favorite Steak House on the Upper East Side) and then go to a Broadway Show. But, Kevin had other plans. The truth is…Kevin had bought a ring. He told his parents (Steve and Laura) and Jaclyn’s parents (Tina and Scott) to come to NYC and hide inside TBar to surprise Jaclyn after he popped the question. So, early in the morning on that Thursday, Steve and Laura drove in from Monroe, NY and Tina and Scott flew in from Chicago The plan was in motion. Kevin even hired a photographer to be waiting outside the restaurant to capture the moment. Nothing was going to ruin the surprise. At 5 pm, Jaclyn and Kevin hopped into an Uber to head to TBar. She had no idea that her life was about to change. That is, until they arrived at the restaurant and stepped out of the car. As she sprinted to the door to get out of the rain, she saw a bald head darting back and forth in the window of the restaurant. She asked, “Why is my dad here?” Kevin said, “Hold on a minute.” And he got on his knee and asked her to be his wife. For Jaclyn, things got fuzzy. She said, “Is this real life? I think I just blacked out.” Then she screamed a little. Actually, a lot. And then she said, “YES!”