The story begins at a tater tot festival in San Francisco; however, neither Colleen nor Jim was there. Luckily, two of their mutual friends made plans to meet up and enjoy the scrumptious food. Carrie and Jess became friends when they met at their gym in Boston and happened to both move out to San Francisco. And so, while enjoying some assuredly tasty tots the plan to set up Colleen and Jim was put in motion. After some texting back and forth, Colleen (finally) asked Jim if he'd like to meet in person and they agreed to meet for lunch. The conversation was so great that Colleen and Jim stayed at lunch for over 3 hours. They said their goodbyes and that they’d both like to see each other again. As soon as they parted ways, Jim wanted to let Jess know how the date went. He erroneously texted Colleen and said "Colleen's pretty awesome. We just had a 3 hr lunch lol". Both Colleen and Jim had a good laugh at this mistake!

Jim asked Colleen if she'd like to go for a walk on Commonwealth Avenue to see all of the holiday decorations before going to dinner. Commonwealth Avenue is a beautiful street lined with trees; each holiday season, the trees are covered in white lights to create a beautiful canopy of lights to walk under. Right before they reached the Boston Public Garden, Jim stopped, turned to Colleen, and got down onto one knee while saying he'd be remiss to go into 2019 with a girlfriend instead of a fiancée. Colleen cried and said yes!