1.If you know that the guy is a Knicks fan, get front seats to a Knicks game and then prevent him from watching the final. Send him to the refreshments stand to get you a Coke instead, ensuring that he misses seeing that last crucial game-winning basket.
2.Take him to a chick flick marathon. If that isn't annoying enough, quiz him throughout the movie about what he's thinking. Ensure that a big beefy fan of Sleepless in Seattle gets annoyed and sweetly tell him that your boyfriend could wipe the floor with him. Only be comforting after the guy gets a black eye.
3.Let him cook dinner for you-...
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