Dear John;

I’ve been with my husband for 14 years and am considering leaving him.

He can be horrible to me sometimes, especially when he has a drink, and calls me expletives regularly for the dumbest of things. Whenever I want to talk about how I’m feeling about us, he isn’t ready to. I’m not allowed to express any feeling that he doesn’t like. It’s always when he wants to. He has told me he wouldn’t be able to live without me, and I’m afraid that that could be true. I’m at a loss for what to do.

-Anonymous from Texas

Dear Anonymous from Texas,

Creating new boundaries can be challenging, but advocating for what you need is worth the friction. Sometimes we fear change so much that we’re willing to stay in situations that no longer respect our wants and needs. Tell your husband a specific time and date that you would like to talk, establish consequences if he doesn’t participate, and be prepared to hold him accountable if he won’t respect your request to talk about the things that matter to you.

Dear John; 

I had a boyfriend that I was with for six years. We broke up many months ago, but he asks for money, it seems, all the time. He cheated on me when we were together and has some drug problems that I wasn’t aware of when we were together. I want him to get better and be the person I thought he was, but I can’t keep supporting him. I know I should not be giving him money, but how do you cut someone off that was so connected in your life? I don’t want him to suffer.

-Jason from Georgia

Dear Jason,

Love can be complicated and irrational. It is normal to struggle to separate your mind from your heart. Enabling often begins with good intentions because you want to help a loved one, but allowing the behavior can lead to codependency. Ask yourself if you believe your financial support is helping your former partner move toward a healthier, more stable version of themselves or further away. Cutting someone off financially can create volatile emotions, and you may need support to navigate breaking away entirely from the cycle of financial abuse. Seeking counseling or group therapy can be a significant first step in reclaiming your financial and emotional boundaries.

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John Porter is an entrepreneur and founding partner at Oasis Asset Management. He has served as a political organizer and strategist within the Democratic Party, as well as serving as an executive board member for the Miami Yacht Club.