For six months, I played the role of the generous friend—covering brunches, coffees, dinners—because Jenna always “forgot her wallet.” I didn’t mind at first; friends help friends, right? But the excuses piled up, and so did the debt. Nearly $700 later, I realized I was being taken advantage of. Her charm masked a pattern, and my silence made it easy for her to keep exploiting it.
The final straw came on her birthday. She ordered champagne, steak, dessert—the works—and then smirked, “You guys don’t mind covering me, right?” Everyone looked at me, expecting the usual. But something snapped. I met her eyes and said, “Actually Jenna, you’ve been covered for months. Tonight’s on you.” The room froze. She laughed nervously and claimed she’d run to the ATM.
She never came back. No goodbye, no apology. Just vanished. That moment was painful, but liberating. I realized I’d been paying for more than meals—I was funding someone’s entitlement. Losing the friendship hurt, but losing the guilt and resentment? That was priceless. I’d finally drawn the line.
We haven’t spoken since. And honestly? That was the cheapest $700 lesson I’ll ever learn. Boundaries matter. Generosity without respect becomes a trap. I’m done being the fallback wallet. From now on, I pay with intention—not obligation.
