“Will you be okay?” – Sounds a little self-aggrandizing. What she hears is, “How will you survive without the divine blessing of my presence? Without this chiseled bod and righteous beard?” If you want to sound concerned without sounding condescending, say: “If you need to talk, I’m around.”
“You’re going to find someone so much better for you.” Right after you’re done talking, I’m going to go kvetch about all your flaws to my friends. When they say I’ll meet someone better, I’ll be touched. When you say it, I’ll burst into tears and spend the next few hours wondering whether you’ve already met someone else.
“I hope we can still be friends.” “It’s the worst, because there’s no closure,” one friend said. Besides which, when the dumper tries to initiate a friendship, it sounds like he wants to have his cake and eat it too-that he wants to date other people while still enjoying the dumpee’s good qualities. If you’re ever going to be friends, it’s up the dumped party to initiate it.
“Good luck.” Where “I hope we can still be friends” doesn’t quite provide enough closure, “good luck” is like a closure bomb. If you want the dumpee to know you wish them well and will continue to care about them, say: “If you feel like it, give me an update on [specific personal or professional thing they’re stressed about.] I’m still rooting for you.”
“I’m sorry you’re upset.” Even if you’re not actually upset about a breakup, you should mirror the response of the person you’re dumping: If they’re devastated, you should try your best to look devastated too.