He used to regale us with anecdotes.

Answer: Option C

Bore : make (a hole) in something with a tool or by digging.
Flatter : lavish praise and compliments on (someone), often insincerely and with the aim of furthering one's own interests.
Entertain : provide (someone) with amusement or enjoyment.
Tire : feel or cause to feel in need of rest or sleep.
Regale : entertain or amuse (someone) with talk.

Synonym of Regale is Entertain