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How to help a sister through issues with guys

| Monday, June 11, 2018, 5:57 p.m.

Adapted from a recent online discussion.

Dear Carolyn:

Last night, I received my umpteenth call from my sobbing, devastated sister (mid-20s) over yet another semi-hookup-flirty-thing guy that didn't work out. He is moving away and she found out via an announcement at work, not from him.

This is a years-long pattern. She falls for jerks -- i.e., they consistently bail on plans, girlfriends still in the picture, conveniently call only on weekends -- then is utterly devastated when it doesn't work. She's convinced she is “unlovable,” “boring” and “ugly” even though she is a beautiful, smart, funny, successful, athletic, kind and thoughtful person. She says things like, “I can't do this anymore,” and, “I don't want to do life if this is how it's going to be.” I've tried tough love but she is so fragile she falls apart all over again; I've tried comforting her and telling her what she wants to hear, but I think that reinforces the problem.

Do I keep on with tough love or continue to be her shoulder? This is breaking my heart and I am so worried for her.

-- Tough Love or Shoulder?

What is your definition of “tough love”? Because it's hard to think of anything tougher, long run, than hearing only what we want to hear.

In that spirit, my thoughts:

1) There isn't much bystanders can do to help. It's an incredibly common problem, painful to watch and stubborn as hell.

2) Telling people what they want to hear is never the answer unless there's a gun to your head or they're on their deathbed. (OK, maybe there are a couple of other exceptions, but I'm near the end of my week and I want to go out in a blaze of hyperbole.) Telling people what they want to hear is at its core an act of disrespect. It's: “You can't handle the truth!”

3) With jerk-dating patterns, it's never about the jerks or any given jerk -- so if you're talking about a particular guy, you've already lost the battle and are losing the war. The problem is your sister, full stop.

4) The problem isn't that your sister isn't lovable. It's that her picker is broken: What attracts her to someone is out of alignment with what is healthy for her.

5) I can't identify the emotional problem behind that problem because I don't know her -- but she can, if she has the courage. Big if. The one thing I know for sure is that she seeks out what feels comfortable and familiar to her emotionally (because that's pretty much what we all do), even though in her case what is familiar is not healthy.

6) A good therapist could help her identify what feelings are familiar, what part of that familiarity backfires on her, and why.

So -- what does this mean for you? Not much that feels productive or satisfying, alas, but it's worth a try: Call her back to say, “You're not unlovable, boring or ugly, as you know. But I think you also know on some level that you're repeatedly choosing people who -- for whatever reason -- aren't healthy for you. You're drawn to certain feelings like a drug and these guys supply it. I hope you'll consider talking to a therapist to find out why.”

Email Carolyn at, follow her on Facebook at or chat with her online at noon Eastern time each Friday at

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