Dear Harlan,

My best friend, who is a girl, went through her first real breakup about a year ago with a guy she had dated for around 10 months. She's been distraught ever since and unable to get over it. Whenever he shows any interest in her, she ends up hooking up with him and being upset all over again when she realizes it's a one-time thing. Recently, I heard that he had been with a bunch of girls at college. I decided to tell her to help her get over him. She's been upset since I told her and she confronted him about it. I have two questions: (1) How can I get my friend to finally move on and get over this guy? and (2) How do I handle this situation if confronted by the guy or friends for telling her about what he's done?

Caught in the Drama

Dear Caught,

Putting aside the fact that you might have a painful crush on your best friend, here's what I'd tell my best female friend:

"(insert friend's name) First, you know how much I care about you and want you to be happy. Right? I can't imagine how painful it must be for you to get past your ex, but I wanted to remind you that you are so smart, so attractive, and have so many amazing qualities. There literally are thousands of guys waiting to date you, love you, respect you and treat you the way you deserve to be treated. You deserve the best, and your ex is treating you the worst. Not only is it disrespectful hooking up with you when he knows you want to get back with him, it's unthinkable that he's exposing you to any sexually transmitted diseases he might have. Because I care about you, I'm going to remind you over and over again that you live in a world of endless options. If in a few weeks you still can't see it - I want to help you find professional help. I'm always here for you. Please be good to yourself. Get him out of your life and start living life again. As for how to deal with a possible confrontation with her ex - I'd shut up and walk away. You can't engage a guy like that and win. Defending yourself will just get him to attack you and force her to take sides. Don't play his game, and you will win.