Early November, 2001
While shopping for a birthday gift, Jason walked into a store and saw a part-timer, Diane, working behind the counter. He strikes up a conversation and asks her out. Diane's first thought was that he was a really nice guy, but not her type. She agrees to a date later that week, but calls to cancel the following day.

November, 2001
Later that week, Jason goes back to the store to talk to Diane again and asks her out for another date the following weekend. She agrees, then cancels again.
Jason, being the persistent person that he is, asks her for a date 2 or 3 more times over the next couple months. Each time Diane agrees, only to cancel later.

January 27, 2002
Diane asks Jason to meet her and a few friends at the Safari Club to celebrate her birthday. By this point, Jason assumes she will never go out with him, so he was happy to cultivate a friendship. After spending most of the evening together at the bar, Diane agreed to go out with Jason on a "real" date the following Saturday.

February 2, 2002
First Date - It started out a little awkward (remember, Jason was not really Diane's "type") but as the evening progressed, Diane started to see many qualities that she liked about Jason and readily agreed to a second date.

June 7, 2004
Diane and Jason got engaged. Jason proposed unexpectedly and in a very romantic way - he got down on one knee at a Chicago Landmark, Buckingham Fountain. The wedding date was set for July 16, 2005.