Tricky sentence

Question

If Bob’s favorite chocolate is dark chocolate and Bill’s favorite chocolate is milk chocolate, would you say:

Bob and Bill’s favorite chocolates

Or

Bob’s and Bill’s favorite chocolates

Thank you!

Answer 1

Bob's and Bill's favorite chocolates are dark chocolate and milk chocolate, respectively.

The apostrophe after each name shows possession of one noun (Bob [person]) to another (dark chocolate [thing]). The use of the word "respectively" associates each person with his favorite chocolate in proper order.

The Writer's Dictionary. 2021. Retrieved from What is an Apostrophe? Definition, Rules for Apostrophes - Writing Explained

Answer 2

Each of them has the favorite chocolate, so each of their names will need the apostrophe. It is the kind of chocolate that is the same, but Bob and Bill are two separate people.