I have no wisdom to share on dating.
All I remember is the last time I played a videogame, it was Space Invaders.
If it gets laughs, it's funny.
Many comedians have a dark side that lets them take a negative thing and turn it funny.
If you have an impulse, not if you're going to ruin someone elses' scene, if you have an impulse of a funny little add-on or taking something in a weird direction, try it.