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Ask Polly’s Dating Advice for Everyone

Photo-Illustration: Stevie Remsberg; Photos: Getty Images

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Over the years, the Cut’s advice column Ask Polly, by writer Heather Havrilesky, has offered dating and relationship advice to readers from all across the love spectrum. With her talent for treating each question with a unique and individual level of focus, Polly advises both the lovesick and the lovewell, championing a belief in romance throughout. Below, eight of Ask Polly’s best dating and relationship questions, answered.

Why Don’t the Men I Date Ever Truly Love Me?

When a reader fresh off a breakup wonders if she knows what love is, Polly doesn’t mince words: “This guy was going to dump you no matter what.” She goes on to wonder why the letter focused on herself (and her ability to be loved) without describing herself at all. “Your real problem,” she tells her, “is that you’re sure you have a problem.”

Would He Love Me If I Were Prettier, Skinnier, and Sweeter?

A woman calling herself “Charmed” tells Polly she thinks that if she were “prettier or sweeter or thinner,” her boyfriend wouldn’t have broken up with her. Polly calls the woman’s bluff: “What if I just told you, ‘Yes, it’s true. You aren’t good enough for him.’” Pointing out that any answer to this question wouldn’t change a thing, Polly encourages her to break free from imagining she can reach some kind of ideal self.

Photo: © Eugenio Marongiu/Getty Images/Cultura RF

Holly Craps, Who the Hell He Thinks He Is?

Writing from Bulgaria, Sad Girl has a question about her boyfriend. “So, dear Polly, why he is pushing me away?” she asks. “Why and how his happy eyes became sad in one night?” In response, Polly reminds the reader she doesn’t (and can’t) know exactly what’s inside others’ hearts.

Am I Settling?

A woman in her 20s writes to Polly about feeling restless in a four-year-long relationship. Polly’s response invokes her own dating history: “Eventually, I started to believe that the doubts would always be there. So I got better at living with them — even when it seemed like they were ringing in my ears at night.” But in the end, Polly says, she realized she had to go out into the world alone.

What Am I Doing Wrong With Men?

A woman writes in hoping Polly can provide answers about what’s at fault in her efforts to pursue mean men. With kindness, Polly bats the question back at her, saying it has nothing to do with the men themselves. “You are repeatedly imbuing them with power,” she says, “pretending that they hold the key to your true identity and your true mistakes, when they just don’t.”

Photo: irinamunteanu/Getty Images/RooM RF

Can I Dump My Dying Boyfriend?

Broken Hearts All Around writes of wanting to break up with her boyfriend before his terminal cancer diagnosis. Can she break up with him now? Polly’s response is blunt from the start: “There’s no way I can answer this question for you.”

What Did I Do to Deserve This?

A woman writes from India, where she aches to be able to marry her girlfriend. Polly describes the experience of reading the letter, her happiness, her sadness, and what she now feels is a naïve reaction to an unjust situation in an unjust world. From this place, Polly reminds us, “We don’t have to feel unworthy because of what we have, or unworthy because of what we don’t have.”

Should I Tell Him What I Want?

A reader says she’s dated a “very good man” for half a year, and she can’t help but notice a disconnect between them. Is this something she should bring up? Definitely, Polly recommends. “Tell him,” she says, “what love looks like to you.”

Order the Ask Polly book, How to Be A Person in the World, here. Got a question for Polly? Email askpolly@nymag.com. Her advice column will appear here every Wednesday.

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Dating Advice for Everyone