Should I Tell My Friend I'm Jealous of Their Life? I've Been Congratulating Them for Two Years.

She sent a photo of a key in her hand. Not a fancy key — a plain one with a tag from a hardware store on the ring, and behind it a door with paint that didn't match the frame.
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Should I Tell My Family I'm Not Okay? They Ask Every Sunday and I Say "Fine."

Sunday, seven o'clock, the phone propped against a water glass on their kitchen table so I get the ceiling for the first thirty seconds.
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Should I Stop Waiting for Someone Who Never Promised Me Anything? It's Been Two Years.

I tidy the apartment on Wednesdays. Not clean — tidy. The specific version where you move one thing off a chair and straighten a rug, as if a room could be prepared.
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Should I Break Up With Someone I Still Love? Nothing's Wrong.

I've known for about six months. Not all at once — the way you know a tooth is going to need work, in increments, each time you decide not to think about it.
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Should I Stay With Someone Who Won't Introduce Me to His Family?

Two years. I've met his friends, his colleagues, the guy he plays football with on Thursdays. I have not met a single member of his family.
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Should I Give My Partner an Ultimatum? We've Had the Same Conversation for Eighteen Months.

Four years together. One conversation that keeps happening and never lands.
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Should I Tell My Partner I Earn More Than They Do? It's Never Come Up.

Three years together. We split rent evenly because that felt fair when we moved in, and we've never revisited it. We split dinners. We split trips. It works, and it's a small point...
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Should I Let My Friend Move In With Me? I Said Yes in Four Seconds.

He asked me in a text that started with "so this is awkward." His lease had ended badly, the sublet he'd lined up fell through, and he needed somewhere for a few months. I read it ...
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Should I Move In With My Partner's Parents to Save Money? The Math Says Yes.

Our lease ends in four months, the rent went up again, and my partner's parents have a lower floor with its own entrance that they've offered us twice.
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Should I Tell My Friend What I Really Think of Their New Partner? She Asked Me Directly.

Two weeks ago my friend asked me, in a car, in the specific tone people use when they've been waiting for the right moment: "You've been quiet about him. What do you actually think...
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