Jessica & Jason in Thomasville, GA

Unbeknownst to Jessica Sosby and Jason Roth, their initial encounter -- at a bar in Tallahassee, Florida -- wasn’t really their first meeting. During his preschool days, Jason had lived in Jessica’s hometown. “Upon playing a bit of six degrees of separation with his aunt at a party, we soon realized that I had attended the preschool that she ran, the very preschool that Jason had attended,” Jessica says. “I had even gone to their house on numerous occasions to take swim lessons from Jason’s cousin.” The Bride Jessica Sosby, 27, an admissions officer The Groom Jason Roth, 27, a communications coordinator The Date April 9 Soon the twosome moved to New York City and were approaching their two-year anniversary when Jason asked Jessica to join him on the rooftop late one Friday night. Dressed in a nightgown and a ponytail, Jessica found Jason down on one knee with a ring. “I just gaped at him until he told me to say yes, and I did, falling into his arms,” she remembers.