It was a cold January night in DC and the Obamas had long since left the White House, so needless to say the alcohol flowed freely. Rachel and Caleb met up at an Adams Morgan wine bar, where Rachel elected for the Sauvignon Blanc (which would become a staple of dates to come) and Caleb went with what he could really only describe as "red." After many hours getting to know each other and trading stories from semesters spent in Scotland, they knew this date would be the first of many more. Afterward, Caleb waited three days to text Rachel because that's what every 90s sitcom said you're supposed to do. Upon receiving a text (finally) on Day 3, Rachel eagerly planned their next date.

Growing up watching Letterman as a preschooler (the 11:30pm bedtime absolutely thrilled his parents) and with a family of New Yorkers before him, New York had always held a special place for Caleb. Years later, while he knew that anywhere with Rachel would feel like home, he made the first of what would be two big proposals (more on the second one in a minute). Upon visiting friends in Brooklyn and after taking in an afternoon in Domino Park, Caleb popped the question. "What if we moved to New York?" The ring in this proposal was really more of a proverbial everything bagel, but honestly, is that any less appealing? After a bit of consideration (*gasp* Rachel would need to move North of the Mason-Dixon line for the first time), Rachel happily agreed. One moving day snowstorm later, they settled on an apartment on the Lower East Side, just blocks away from the homes of their respective great-grandparents.

Okay, now for the second proposal. The one with the diamond ring and all. After many months crafting the perfect ring in DC and transporting it to New York (Caleb neurotically never took off the backpack holding the ring throughout the entire move), Caleb knew just the place to take their relationship full circle. Under the guise of a quick walk across the Williamsburg Bridge, Caleb found the perfect spot in Domino Park (get it?) and got down on one knee, ring in hand and Empire State Building in the background. A proposal to make Nora Ephron proud. Rachel excitedly said yes when asked to make this relationship official-official and the rest is history.