Tomorrow night, my family and I are gonna play Trivial Pursuit together. 
That sounds fun!  Which edition are you playing?  Master Edition?  Oooh, or maybe Horror Movie Edition?
We just play the regular edition, but I'll definitely check those versions out. Have you ever gotten the chance to play?
You know hard hard it can be to find others to play with haha.  Who do you usually play with?
I usually play with my family. My friends aren't very into the game. 
Families can often have the best rivalries!  Have you ever tried Family Edition?  Sounds right up your alley!
We should definitely check that out. My family is definitely competitive, and I have never even won. 
That's a shame, I bet you're just waiting for the right questions!  I've heard that some people practice by watching Jeopardy, makes sense when you think about it I suppose.  Who's your biggest rival at the table?
My older brother and his wife. I also do watch Jeopardy to prepare. 
Do you think it's helping?  Apparently Jeopardy Champion Ken Jennings came out with his own game, might be worth a try as well?
I think it is helping and I'll check out his game.