Phoebe responded to a Craigslist ad that James had posted: "3 Comedians Looking for A Roommate." As a comedian, she was excited to meet like-minded individuals in NYC, so she moved in. James and Phoebe immediately enjoyed going to plays, cooking, and staying up talking for hours. So, it didn't take them long to realize they wanted to be roommates (and more) forever!

Before dating, Phoebe and James went to see Diane Lane in the Cherry Orchard on Broadway. There was a beautiful terrace where they could see the twinkling lights of NYC, so Phoebe told James "you should propose to me here." He didn't. Three years later he planned to propose on that terrace, but the theater was closed for renovations. So, he decided to recreate the theater's terrace at their home in the Lower East Side while Phoebe was at rehearsal. But then, rehearsal was cancelled. Twice foiled, they created a new special spot when James proposed on the Manhattan Bridge at Sunset.