The Washington PostDemocracy Dies in Darkness

Every guy I date turns out to be a jerk. So what am I doing wrong?

Ben Claassen III (for Express)

Q. I have a history of dating jerks. I always think they are good guys, and they turn out to be completely incapable of treating me well. My friends see it right away, but I never do. I’ve always said I’m a jerk magnet. Why can’t a good guy like me for once? How can I be better at looking out for signs? —Tired of It

Um, hire one of your friends to never leave your side?

You need a shift from the passivity of “Jerks shall choose to be in my life” to the autonomy of “I shall seek out and select only good people to let in.” What do you really feel you deserve? A lack of confidence or self-worth could be adding to the learned helplessness here.

Ask your friends to stay close, discuss and support. Observe their relationships — how they’ve met good people and created connections. Ask yourself what matters to you in life, from values to interests to how you like to hang on a Friday, and where you can find like-minded people. And do some honest work exploring if it’s not only that you’re ignoring the warning signs, but that you’re actually attracted to them.

A family divide, more or less

Q. My youngish, healthy parents are drawing up documents related to their estate. My father gave me the heads-up that  they plan to leave my sister a larger percentage of the estate because “she needs it more.” That is true, and honestly I do not feel entitled to their money. My husband and I make a very good living and my sister struggles with her career. But I can’t shake being hurt that they took this decision so lightly. Wondering How To Get Past This?

First, don’t deceive yourself. Is the money a symbol, a tangible sticking point, or both? If it’s truly just symbolic, then you can start an honest conversation with your parents and let them know you wish you didn’t feel hurt. If they’re the “Suck it up, buttercup” type, you may get nowhere, and that’s OK.

Ultimately, you’ll get past this by living your life and respecting their choice. You can’t assume they took this lightly; they could have debated it for years. The big picture will come: that they’ve loved and valued you for decades. That they worry for your sister. That money can be simply a logistical tool, not necessarily an expression of emotion. That they have confidence in you not only to be able to support yourself, but to have the grace to let your sister receive help that you don’t need. Hey, that faith in you could be a gift in its own right.

Send your questions for Baggage Check to Dr. Andrea Bonior at

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