Dear Annie: My best friend and I have been close since college. He is the person who helped me move into my first apartment, who showed up with coffee during finals, who still remembers the name of my childhood dog. That is why it hurts so much to watch him repeat the same pattern that already cost him almost everything.

Years ago, his gambling addiction wrecked his marriage and he lost his home. I remember the day he called to tell me his wife was done. His voice sounded hollow, like he already knew he had finally run out of chances. Not long after that, he was sleeping on a friend’s couch and trying to act like it was no big deal. I even helped him pack up boxes from what used to be his house, and I can still picture him standing in the empty living room pretending he was fine.

He has rebuilt parts of his life since then. He works as a Realtor, and when he is doing well, he is funny and upbeat and full of energy. When business slows down, he spirals. He calls me to complain about making ends meet, and I can hear the fear underneath his voice. What makes my stomach drop is that sometimes when he calls, I can hear poker chips clicking and that familiar casino noise in the background. He will talk about bills like he is drowning, but he is sitting at a table.

I have not loaned him money in a long time because I do not trust where it will go, but I have never said that out loud. I want to confront him, but he is a proud and touchy person, and I do not want to create a fight or push him away.

How do I tell him I am worried and draw a firm line about money, without losing someone I love like family? — How Do I Keep My Friend’s Money in His Pocket?

Dear Keep Friend’s Money in His Pocket: The sound of poker chips in the background while your friend worries about bills is not an effective form of stress relief. It is the problem talking.

You cannot keep his money in his pocket, but you can keep your money out of his addiction and keep your friendship honest. Call him when he is not at the casino and say, “I love you and I’m worried. When I hear casino sounds and then hear you panicking about money, it scares me. I’m not going to loan you money, and I don’t want to pretend this isn’t happening.”

If he gets touchy, do not debate or lecture him. Repeat the boundary once and offer one lifeline: “If you ever want help finding support like Gamblers Anonymous or a counselor, I’ll help you.” Then change the subject or end the call.

A friend is a friend, and you are not a bankroll.

“Out of Bounds: Estrangement, Boundaries and the Search for Forgiveness” is out now! Annie Lane’s third anthology is for anyone who has lived with anger, estrangement or the deep ache of being wronged — because forgiveness isn’t for them. It’s for you. Visit http://www.creatorspublishing.com for more information. Follow Annie Lane on Instagram at @dearannieofficial. Send your questions for Annie Lane to dearannie@creators.com. COPYRIGHT 2026 CREATORS.COM