When Robin tells Don that she talked with his rabbi, she says, "I just want to make sure you don't end up on the roof with a fiddle." Rob Morrow has said his first big role was playing Tevye in a high school production of Fiddler on the Roof.
Near the end, Josh Gad's character is asked what he knows about the next year's Super Bowl. He says "Take the points, and the over". In the next Super Bowel after the show aired, Pittsburgh won 27-23, but was favored by 7. The over/under was 46. Both bets would have won.
In addition to Rob Morrow's connection to Fiddler on the Roof, guest star Paul Michael Glaser was also in Fiddler on The Roof.