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.

不要說"You were too good for him."(他配不上你。)因為這樣說的話你本質上是指她的品味太差，而且萬一他們言歸于好了你豈不是很尷尬?可以說"His loss!"(那是他的損失!)這樣既沒有貶低她的判斷能力，又達到了同樣的效果。

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.

不要說"I’m glad you got rid of him. I never liked him anyway."(我真高興你甩了他。我從來就沒喜歡過他。)那樣她會懷疑，他倆還在一起的時候你不過是假惺惺地稱贊她男友。可以說"I’m confident you’ll find someone who will give you exactly what you want."(我相信你會找到稱心如意之人的。)這話著重于將來會如何，而不是那段失意的過去。

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.

不要說"How could someone as perfect as you still be single?"(像你這樣十全十美的人，怎么還會是單身呢?)這感覺像是句諷刺挖苦的恭維話，在她聽來你是問"What’s wrong with you?"(你哪里不對勁?)可以說"Seeing anyone?"(有沒有約會啊?)如果她對自己的戀愛問題守口如瓶，那就轉移話題吧。