I didn’t hesitate when my younger brother, Darren, lost his job. I immediately sent him $3,000 to cover groceries and rent, believing it was my duty to help family and give him time to recover. I’ve since learned the hard way that enabling someone can look deceptively like support—until it’s too late.
Two weeks after sending the money, I noticed his girlfriend, Rita, posting photos from trendy restaurants and flaunting expensive designer bags. I tried to give Darren the benefit of the doubt. But then I came home to find my television missing. My emergency cash, a pair of sneakers, and my gaming system were gone from the back of my closet. Darren was the only other person with a key.
I called him. It went straight to voicemail. I texted, "Did you take my stuff?” No response. Since he’d been staying at our mom’s house, I went there the next morning. He was lounging on the couch as if nothing was wrong. "Where is my stuff?” I asked. He didn’t even flinch. "I pawned it. Relax—I’ll get it back once I get a job.” I was stunned. "You stole from me after I gave you money?”
"You live alone,” he shrugged. "No kids. You can afford it.” My mom jumped in, making excuses, saying he just needed time. In that moment, I realized this wasn’t love or compassion—it was enabling. That afternoon, I filed a police report. My hand shook as I filled out the paperwork, but I knew I had to protect myself.
Two days later, Darren called me, furious. "You called the cops on me? That’s cold.”
"No,” I replied. "Stealing from your own brother is cold.”
Although my TV was gone for good, I managed to recover some items from the pawn shop. I changed my locks and blocked his number.
Weeks later, I received a call from a stranger named Marissa. She told me Darren had scammed her cousin too, taking money and lying about his success. Soon after, my mom called—Darren had been arrested for online fraud. He was finally facing consequences. She urged me to go see him, insisting he needed help. I told her he didn’t need support just yet; he needed a mirror.
In January, Darren was sentenced to probation and mandatory rehab. I ran into him at the grocery store a few weeks later. He seemed calmer, more aware. He handed me a repayment plan: $100 every two weeks. I accepted it—not for the money, but because it was the first time he was taking real responsibility.
Now, eight months later, Darren is repaying me, working at a warehouse, attending therapy, and slowly rebuilding our relationship. I recently invited him over for dinner. During our conversation, he asked, "Do you still think I’m a screw-up?”
"No,” I said. "Because you finally stopped blaming everyone else.”
I learned one of life’s toughest lessons: that grace can sometimes enable poor behavior. The most loving thing I could do was to set boundaries—to report him and cut him off. It was for my sake, not just his. I realized that love shouldn’t cost you your peace, and I am not responsible for someone else’s rock bottom. Sometimes, love means stepping back and allowing someone to face themselves.
