Stop the daily phone calls and bean dip him if the ex is brought up.

mrsconn23

Dear Prudence,

I talk daily with a close friend. He frequently turns the conversation to an ex of his—he psychoanalyzes her, speculates on how she’s handling major life events, compares other people to her, etc. It’s been close to a year since their tumultuous breakup, and I’m honestly so tired of talking about her. It never changes either of our opinions and leaves me annoyed and frustrated. How can I politely but firmly say that I won’t discuss her anymore?

—Totally Talked Out

short+sassy

Instead of being annoyed, though I don't blame them, the LW should ask their friend if he is still struggling from the break-up.  Point out that she is still a frequently brought up topic and they're worried he is thinking about her too much.