Last June, I was in Vegas for the NHL Awards. The Sharks were getting 55-1 odds and my buddy had me put a $50 bet for him. When they made the Finals, I figured I was in a good spot.
A) If the Sharks won, I could be happy for him to use that money towards his wedding later this year. He also promised to treat me to a nice meal for putting the wager down.
B) If the Sharks lost, I could make fun of him relentlessly for almost winning. Or be the annoying second guesser "I would have just bet on them winning the Conference."
His birthday is in a few weeks. I'm probably gonna be a jerk and get him a Conference champions shirt/hat if they go on clearance in time.