Both Demetra and Blaine had been living in New York City for a long time before their paths crossed. Blaine initially moved to New York for college, and Demetra moved there for a dot-com job. In March of 2008, one of Blaine's friends (Josh) went to a party and met Demetra. They both had a great time that night, but something seemed a bit off – besides the fact that Josh was lying about his age to impress Demetra. After the evening was over, Josh felt that his friend Blaine would be a better match for Demetra.

Josh proceeded to play the matchmaker and contacted both Demetra and Blaine to set them up. Blaine thought it was strange but was curious, and Demetra took it almost as an insult. After letting a few days pass, Blaine looked Demetra up on Facebook, and decided to give it a try by emailing her. Initially, Demetra had no intention of replying, especially after seeing some of the outrageous pictures of Blaine that he’d posted online (i.e. entire body painted for Bay-to-Breakers, and another with his head painted like a soccer ball for the World Cup 2006). However, after some trusted friends told her “you would be stupid not to” reply, because “you never know”, she decided to do it! A couple of days later, Blaine called Demetra, and they completely hit it off on the phone.

A few nights later, on Tuesday, March 25th, 2008, Demetra and Blaine had their first date at a West Village bar called Employees Only. Instantly they hit it off, conversation flowed as smoothly as the drinks, and after a few of the tasty cocktails, they both realized that this could turn into something.

Not long after that first date, Blaine was traveling from DC to Philadelphia for playoff hockey (Caps-Flyers, first round games 5-7). He realized that his trip would require a detour back to the West Village in between games because he could not wait any longer to see Demetra. It turned out that Blaine was suddenly hooked on more than hockey! And that was just the beginning…