Jenn & Matt in Watertown, MA

Sometimes even the best-laid plans take an unexpected turn. When Matt was getting ready to propose to his girlfriend of six years, Jenn, in September of 2004, he thought he had timed everything perfectly. Jenn was supposed to be taking an eight-hour class at Northeastern University, during which time Matt planned to drive to Rhode Island, pick up his future fiancee’s engagement ring, drive back to Massachusetts to her parents’ house and ask for their blessing, and then pick up Jenn from school for the big surprise. Jenn, however, had other plans, including a stop at the mall. The Bride Jennifer Guevara, 27, financial services The Groom Matthew O’Donnell, 27, senior accountant The DateOctober 22 While the two were browsing around Filene’s Basement, they happened upon the costume jewelry counter. As a joke, Jenn purposely started trying on the biggest cubic zirconia rings she could find, saying to Matt that she was a “two-carats-plus kind of gal.” Little did she know he had the real thing waiting in his pocket!