I'm tutoring an introductory course in statistics next semester so I would like to give my students some fun counter-intuitive problems to think about.
There are some famous problems like the Monty-Hall problem or the Birthday Paradox, but I feel that many students would most likely already know those.
What are some lesser known probability problems with paradoxical or counter-intuitive seeming solutions?
Cheers!

Here's an activity that is fun to have students make predictions (guesses) first, and then simulate:
Imagine giving $100$ gifts to $100$ children so that each gift is equally likely to go to any of the $100$ children, independently of what happens with any other gifts (i.e., equivalent to putting $100$ names in a hat and doing $100$ draws with replacement from the hat).
You can ask questions such as: How many children will not get any gifts? How many children will get exactly one gift? How many gifts will the 'luckiest' child get?
You can also extend to asking...If there is an unlimited number of gifts, how many gifts will be distributed until each child has gotten at least one gift?
Usually the predictions are off by quite a bit from what actually occurs.