Former "Blonde Charity Mafia" star Katherine Kennedy marked two significant milestones this week: a birthday and an engagement to boyfriend of two years Grant Allen, a senior vice president at ABB Technology Ventures.

Kennedy, a principal at the Availor Group, tells Yeas & Nays that the two originally met at Old Glory in Georgetown and became friends first, before having their first official date at the Capital Club's Santa Soiree. For the proposal, Allen marked on their shared Google calendar that they would be going on a surprise trip. "Pack a bikini and hiking boots," Kennedy said she was instructed. The couple spent three days at the St. Regis Bahia Beach, first celebrating Kennedy's birthday. The next day, Allen popped the question. "He wanted my birthday to be about me and the next day to be about us," she said. As of now, the couple plans to wed in fall 2013.