Clare and Jonathan met at a graduation party for Clare's brother's best friend, Matt A. Matt A and Jonathan's sister, Meghan, were dating at the time. Clare knew Meghan for almost 5 years and had no idea she had a brother, let alone two. Clare went to the graduation party with her family, and Jonathan went to the party with his. Clare's mom spotted Meghan's two brothers and asked her to introduce them to Clare and her cousin, Hillary, who was visiting at the time.

Clare and Jonathan were introduced over cake at the graduation party (with a mouth full of cake to Clare's embarassment). They stole glances at each other from across the room during a game neither were interested in. They were then introduced again after the cake....and again many more times the rest of the night. It became an ongoing joke between Clare, Jonathan, and her cousin.

Clare and Jonathan got engaged on March 31st, 2015. After many years of joking about when and how to get engaged, he finally popped the question, to Clare's surprise. Clare had an idea that the proposal could be a possibility when Jonathan suggested a nice restaurant for the normal date night. She thought her chances were ruined, however, after the harassment of Jonathan the night before by her friends on the topic.

Jonathan met Clare at her house and waited for her to get ready. He met her upstairs when she finished getting ready and told her he had something for her, and reached into his pocket. He then laughed as her expression changed when she realized it was not a ring he took out of his pocket, but a palm cross his grandfather had made. They walked downstairs and he did it again, saying he forgot to give something else to her, and reached into his pocket again. Although she was on guard, hope was still there and crushed when he pulled out zoo passes for a friend of theirs. After Jonathan had a good second laugh, they went to the fancy restaurant.

They checked their coats, ordered a nice bottle of wine, and spent the dinner joking about how and when he would propose. Jonathan suggested a nice April Fools proposal, but Clare quickly shot that down. After a dessert on the house, they returned to Clare's house for the night. Before Clare could open the door, Jonathan asked if she wanted to tell her coworker friends (the same from the night before) something the next day (April 1st). Confused, Clare turned around to see Jonathan on her front porch on one knee with a ring box out. She yelped, "I need to put these down!" and put down the leftover bottle of wine and purse before Jonathan could pop the question. He asked, and she said, "Yes!"