yes
Question and rationale: The question is: Is H's most common two letter pair partner a freebie in Wheel of Fortune bonus round?
H forms the most common two letter pair in the English language along with the letter T. The Wheel of Fortune bonus round gives the player six free letters: R, S, T, L, N, E.

no
Question and rationale: The question is: Was Jackson Pollock trained by Leonardo da Vinci?
Leonardo lived during the Italian Renaissance in the 17th century. Jackson Pollock lived during the 20th century.

yes
Question and rationale:
The question is: Has Justin Timberlake ever written a song about Britney Spears?
Justin Timberlake and Britney Spears dated in 1999. In 2002, Justin Timberlake released a music video for his breakup song 'Cry Me A River' and featured an actress who resembled his then ex Britney Spears.