Miss Advice: September 2026

September is when everyone returns from summer pretending they’ve changed. New routines, fresh goals, cleaner calendars. Give it three weeks. By October you’ll be eating crackers over the sink and avoiding someone you slept with in August.

Dear Miss Advice,

My friend constantly complains about being broke, but every weekend she’s out for dinner, ordering drinks and buying concert tickets. Then she tells me she can’t afford to pay me back the $80 she owes me. Am I being petty? — Apparently I’m a Bank

Dear Bank, don’t ask for the money back. Make it weird instead. Every time she orders a drink, say, “Oh good, my money’s having fun.” If she buys concert tickets, ask what seat your $80 got. Eventually she’ll either repay you or stop inviting you places. Financial victory either way.

Dear Miss Advice,

I’ve been seeing a guy for about two months. We go out, stay at each other’s places and text every day, but whenever I ask where this is going he says he “doesn’t like labels.” What does that actually mean? — Label Maker

Dear Label Maker, it means he likes labels just fine when they say whiskey, Wi-Fi or “reserved.” The label he dislikes is boyfriend. Stop asking where it’s going and start introducing him to people as “the guy I’m temporarily sleeping with.” You’ll be amazed how quickly he develops an interest in terminology.

Dear Miss Advice,

My boss keeps emailing and texting me after work. Nothing is ever an emergency, but I feel like I’m expected to answer. How do I make it stop without looking difficult? — Off the Clock

Dear Clock, reply immediately, but badly. At 10:14 p.m. send “K.” At 11:03, send a thumbs-up. If they ask for a document, reply “interesting.” Within a week your boss will realize contacting you after hours creates more problems than it solves. This is called workplace conditioning. Pavlov had a bell. You have passive aggression.