Adam Milligan & Tefe Holland
Adam was the least troublesome Winchester in a whole lot of ways.
"This is definitely not the worst speed dating event I've ever done. That honor actually goes to the very first one there ever was, by virtue of the fact that A: it was a couple weeks after I got here and B: I was mildly crazy at the time."
Never mind that it was where he'd met Finch, it still won the honor of worst overall.