Should I Charge My Friend for the Work They Keep Asking Me For?

My friend started a small business eighteen months ago. It's good — the kind of good that comes from someone with actual taste doing something they care about. And I've helped her ...
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Should I Sell the House My Ex and I Still Own? He Moved Out Two Years Ago.

We bought it together. Four years later he moved out, and we did that thing that sensible people do: agreed the house was a shared asset, promised to deal with it properly when thi...
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Should I Lower My Price for the Client Who Says They Love My Work?

The client has been with me three years. They say the work is "exactly what we needed" every single time. They also pay late roughly half the time, ask for small extras as favors, ...
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Should I Give My Parents Money They Haven't Asked For?

My parents are fine. Not wealthy — fine. My father still works because he wants to. The house is paid off. They split a meal at restaurants and think nothing of it, because that's ...
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Should I Get a Roommate to Afford the Place I Want? The Math Takes Four Minutes.

The rent went up 12% this year, as usual. I can cover it — by taking my grocery budget somewhere I don't like looking at, and by knowing that one bad month would put me on a credit...
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Should I Buy the Business I've Been Managing? He Offered It to Me First.

I've run this place for six years. Not owned it — managed it. There's a difference and I've felt every inch of it: I make the schedule and not the budget, I fix the problems and no...
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Should I Get a Prenup? My Fiancé Thinks It Means I Expect Us to Fail.

I brought it up over dinner, in the tone people use for logistics. "I think we should talk about a prenup before the wedding stuff gets busy."
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Should I Cosign a Loan for Someone I Love? I Said Yes Before I Thought About Month Four.

My brother asked me in a parking lot. That's not a detail I'm inventing for effect — he'd driven to my place, we walked out to his car, and he stood there with his keys in his hand...
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Should I Tell My Partner About the Debt I've Been Hiding? It's Been Two Years.

The secret has a schedule. Every month, on the same day, I move money from my checking account into a credit card payment I've never told my partner about. It's been two years. The...
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Should I Take the Freelance Gig? The Money Would Help. So Would a Boundary.

The message came from a former colleague on a Tuesday evening: "Hey — we're slammed. Would you be open to some freelance on the side? Good budget, flexible hours, your call on scop...
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