I would rather play Jeopardy against Spock, as he has consistently demonstrated a lack of comprehension when it comes to pop culture.
Would you rather listen to Wesley Crusher sing karaoke or Kathryn Janeway attempting opera?
Would you rather listen to Wesley Crusher sing karaoke or Kathryn Janeway attempting opera?

But, on the other hand, I could also tell Data not to tell a soul, and he wouldn't, so in some cases, Data might be the better choice.