I graduated last May, have landed my dream job and have an amazing boss. This will be my first holiday season with this organization. Should I offer my boss a gift?

Congratulations on your graduation and new position!

Giving your superior a gift may be perceived as seeking favors, and for that reason you should avoid giving your boss a gift. If there exists a tradition of gift giving to the boss, I would recommend a group gift where everyone is in it together and any perceived or attempted favouritism is eliminated. I would also recommend a hand-written card. It is a much-appreciated way to acknowledge a holiday, a celebration or one's gratitude.