Don’t say: “You were too good for him.”
Why: You are basically saying she has bad taste. And you’ll be embarrassed if they ever patch it up.
Instead say: “His loss!” It gets the same point across without disparaging her judgment.

Don’t say: “I’m glad you got rid of him. I never liked him anyway.”
Why: She’ll wonder about your fake adoration for him while they were together.
Instead say: “I’m confident you’ll find someone who will give you exactly what you want.” It focuses on what’s to come, not on the dud you’re glad she’s done with.

Don’t say: “How could someone as perfect as you still be single?”
Why: A statement like this comes off as a backhanded compliment. What she hears is “What’s wrong with you?”
Instead say: “Seeing anyone?” If she’s tight-lipped about her love life, move on to other topics.

Expert: Bethany Marshall, Ph.D., a psychotherapist in Beverly Hills and the author of Deal Breakers: When to Work On a Relationship and When to Walk Away