In August 2017 on a hot summer night, Clare & Ryan both happen to be dining at Volare, a small and quaint Italian restaurant in Chicago, IL. Clare was celebrating her birthday with her dad (John) and step-mom (Lisa). Ryan, who was new to Chicago, was out to dinner with a friend from the Chicago area. If anyone knows John Jacobs, they know he sparks up a conversation with strangers, so while dinner was wrapping up, John engaged in small talk with two gentlemen at the table next to them, which happened to be Ryan and his friend. Small talk quickly turned into friendly banter between the two tables. Shortly after, John and Lisa left for the evening, and Clare stayed for one more glass of wine with Ryan and his friend, ending the night with more friendly conversation. As the night wrapped up, Clare and Ryan parted ways and never spoke or connected again, until three years later. In November 2020, Clare and Ryan naturally reconnected, went on a date at Bar Sienna in Chicago, and have been inseparable since. After their first date, they both separately claimed "I met my person" and now can't wait to continue writing their love story with their soulmate. Thank you, John Jacobs, for being the best matchmaker:)

Quickly after Ryan finished his season with the New York Knicks, Clare and Ryan jetted off to Chicago to visit with Clare's family and friends, and more importantly, spend time in the city where they fell in love, dine at their favorite restaurants, and enjoy the things they love to do together in Chicago. One of their favorite pastimes is walking along Lake Michigan's beautiful lakefront with a cup of their favorite coffee, La Colombe. So, on the morning of April 16, Ryan suggested to grab a coffee and take a walk on the lake before meeting up with their friends for brunch. Although Clare had a small inkling given it was fifty degrees and she was wearing heels, she soaked in every moment as Ryan grabbed her hand and whispered "you know what's about to happen". On that sunny Saturday afternoon, Ryan guided Clare toward the lake, got down on one knee, and asked Clare to spend the rest of their lives together, be his wife, and continue building a life together. Of course she said YES!

Although Clare and Ryan met and fell in love in Chicago, Ryan's basketball career took them to a new city and state that neither had ever visited nor knew much about- Portland, Maine! While they were thrilled for the next step of moving in together, relocating to a new city and state with no friends or family can be a bit intimidating, but Clare and Ryan quickly embraced the adversity by exploring their new temporary home. Their explorations naturally led them to quickly fall in love with the city's amazing food, beautiful views of the ocean, and the quaint, historic charm. Clare and Ryan enjoyed living in Maine and exploring the nearby towns, especially Kennebunkport. When thinking through places to get married, Maine was a no brainer as it is a sentimental place where they embarked on a new life journey together and a place they will always go back to visit with such fond memories. They've also learned that not many friends or family have had the chance or reason to visit Maine, and the couple agrees it is absolutely a trip everyone should take at some point! They are so excited to gather all their loved ones in such a meaningful place to celebrate their marriage. Although they are getting married in Kennebunkport, the couple highly encourages their guests to spend time in Portland and visit the nearby coastal towns if time allows!