It was Caitlin’s Mom’s surprise birthday party. Cait was chatting with James’ Aunt Kathleen about her life on the dating apps. After a few cringeworthy dates, she knew she wanted an organic connection. Kathleen started describing James, this really good guy who lived just a mile away in Woodside. Caitlin debated -- until she saw his photo. James and Caitlin texted for a month before Caitlin agreed to a date. She'd only wanted to go for a casual drink. If things didn’t work out romantically, she figured she'd at least make a new friend in the neighborhood. But James persevered. Finally, she agreed to go to dinner. On February 6, 2016, James picked Caitlin up and took her to dinner at a Mexican restaurant, Tequila Sunrise. They had such a good time talking, they could barely order dinner. After dinner, the two walked the neighborhood before ending up in a local pub, The Copper Kettle. They got drinks and a booth, talking and laughing together until they closed the pub. They've been inseparable ever since!

Okay, first of all the proposal was not planned for Star Wars Day, it just kind of happened… May the Fourth Be With You! As James rode the subway home from the Diamond District, engagement ring in his pocket, he couldn’t help but think, “The ring is so amazing, it needs to go on Caitlin’s hand.” James considered turning around, going back into the city to wait for Caitlin to get out of work. He would ask her to marry him right there, at her job, in his dirty work clothes. Fortunately, he came to his senses and remembered what he had planned. In less than two days, they were headed to Ireland. He told Caitlin’s Mom he'd consider waiting until later in the trip to propose with the whole family there. But, he couldn’t wait. He knew that ring belonged on Caitlin’s finger. It felt right. The Force was strong on May Fourth when they landed in Dublin. Things just fell into place as the day progressed. The (very small) rental car was brand new. The hotel upgraded them to a suite with a view of the River Liffey and checked them in hours early. After unpacking and showering, James was quickly dressed and hurrying Caitlin along in his usual maner. “Hurry up, come on, let’s get out and see Dublin!" They walked out of the hotel and started to cross the first bridge they saw over the river, The Grattan Bridge. In the middle of the bridge, James tried distracting Caitlin. Confused, she looked back over her shoulder, trying to see what he was looking at. When she turned back around, James was down on one knee asking her to marry him. She said “Yes!” and they hugged and kissed and cried with so much happiness! It was the best day ever!