It took two, but I did it!

Attempt 1:

At a pub quiz, Susannah encouraged me to ask the bouncer to fulfill my challenge. However, I told him the parameters were to take a picture with a stranger. Silly me!

Here he is

Attempt 2:
I was coming out of the Amherst College locksmith and saw a boy walking by. Without thinking too much, I said, "Excuse me, can I ask you a really weird favor?!" Then he agreed, especially after I explained what the WHOLE CHALLENGE was. "Do I really fit the parameters?"

Score one for me! Then, to add awkward to awesome, his friend comes by while my camera is taking its sweet ever-loving time to load. HAHAH. "What's up?" "Just taking a picture with this random girl?" So afterward, I was thanking him -- I never got his name -- and he was like, "Any time." It was awkward, sweet, and lovely. My three favorite things ever. AWESOME.
Also, he was much cuter than the picture, I swear.