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Dear Wendy: “My Best Friend Keeps Falling For Jerks”

I have known my best friend since we were six years old and she’s a great girl. She’s super smart, pretty, and fun, so obviously she has a lot to offer a guy. A few years ago, her boyfriend (who she referred to as the love of her life) moved to another continent, and while they tried to deal with the distance as best they could, they eventually broke up. In the years since their breakup she’s made some pretty horrible decisions when it comes to guys. And it’s not just that I don’t like the guys she’s dated. She let’s them walk all over her. She hasn’t made the safest decisions when it comes to her sex life either. At first I thought she was just going through a bad boy phase. She’d find a new guy and gush about him all the time, then call me in tears. I’ve picked up the pieces more times than I can count, and I try to support her, but I feel like it’s come to a point where I can’t watch her put herself through it anymore. I want to confront her about it, but I don’t want to seem like I’m scolding her. What should I do? — Over the Drama

As much as seeing a friend continually self-sabotage her happiness by following a pattern of dating bad men, it’s a true buzzkill being the one to always help her pick up the pieces each and every time her “relationships” implode. You didn’t sign on to be her therapist; you’re her friend. It’s not your job to counsel her through every (repeated) bad decision she makes. Furthermore, if those bad decisions are beginning to affect your happiness, you have to stand up and say something for yourself. So don’t think of confronting her as scolding her — think of it as clearing some toxic energy in your own life.

Here’s what you do: take her out for a nice lunch/brunch/drinks/what have you and tell her that you love her and you’ll always have her back but you’re getting tired of watching her self-destruct through making the same bad decisions over and over. Tell her you think she could benefit from therapy to help her deal with the residual emotional pain of losing the “love of her life” a few years back and to help her understand why she repeats the same mistakes when it comes to guys. And then be honest with her: tell her that as much as you care about her happiness and emotional well-being, you’ve got to look out for yourself and right now it’s become too draining to be the one she turns to when things don’t work out with the bad boys she always chooses. Explain that in the future, she needs to unload on someone else (like a therapist), but that you’ll be there when she’s ready to confront her issues and quit using men as a distraction from her emotional roadblocks.

You’ll need to be prepared that your friend isn’t ready to confront her demons. She may see your “intervention” as turning your back on her, and there’s a very real possibility she’ll turn her back on you. But the good news is if you’ve been friends since you were six, there’s probably not much that will keep you apart for long. Like letting a daughter grow up and make her own mistakes, you’ve got to let your best friend fall a few times on her own before she learns that tripping over the same stupid bump in the road sucks and she needs to either take a new path or watch where she’s going. As long as you’re always there to help her back up and bandage the scrape, she’s not realizing the extent of the damage she’s doing to herself. You’ll be doing you both a favor if you let her go. It’s what a true friend would do, and hopefully it won’t take long for her to realize that and thank you for it.

*Do you have a relationship/dating question I can help with? Send me your letters at dearwendy@thefrisky.com.

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