Knowing I'm most likely to lose any conventional game, after a bit of thinking I'd challenge him to a contest of who can find true love first, I mean if I lose that to a robed skeleton perhaps it's time I die anyway. Moreover I'd imagine we'd both enjoy that and it would stretch over enough years to give me time to come to terms with the possibility of dying.
Also considering how accident prone I am, what if I had challenged him to a more physical sport and did something that would kill me in the process?