My Boyfriend Always Expects Me to Pay, So I Decided to Teach Him a Lesson

Dating can be a minefield, and sometimes the biggest red flags wave right in front of us, masked by charm and empty promises. If you’ve ever felt like you’re constantly picking up the tab, both financially and emotionally, then this story from a Bright Side reader might hit close to home.

This is what she wrote us:

Hi Bright Side!

I’m seriously reeling from what happened last night with my boyfriend, Will. For seven months, he’s had this pattern of never paying when we go out. It’s every single time — “card declined,” “forgot my wallet,” “just paid a huge bill, can you cover it?” Always with the promise, “The next one is on me, for sure!” But that “next one” never happened. I’ve been footing the bill for everything, and honestly, it feels so disrespectful.

I tried talking to him, but he’d just shrug it off. I was already fed up, but on my birthday, at this ridiculously fancy restaurant, I thought, maybe he’ll step up. I gave him one last chance. But as the waiter approached with the check, Will started his usual routine, patting his empty pockets. “Oh, babe, you are not going to believe this, but...” That was it. My patience snapped. Furious and devastated, I just said, “Oh, I just need to pop to the ladies’ room,” grabbed my tiny clutch, leaned toward the waiter, quietly told him to bring the check to the table, then walked straight out the front door.

Outside, hands shaking, I quickly transferred my half of the bill to his banking app with a message: “Happy Birthday to me. This one’s on YOU for a change. Don’t call me.” My phone immediately blew up with texts and calls. When I listened to voicemails, he was livid. Not concerned, just pure rage he had to pay his own share. “You selfish, childish gold-digger!” he screamed in one message. “How DARE you abandon me?! You’re irresponsible and pathetic! You just ruined my night!”

So, yeah. I guess I got my “backfire.” He hasn’t texted me since. Was I wrong? Did I handle it badly? What do I even do now? This feels like a giant red flag, and I’m so lost. Any advice?

Sincerely, Rachel

Don’t Dismiss What You’re Feeling

Rachel, it’s completely understandable to feel angry, disrespected, and lost after an experience like this. Your feelings are valid, and it’s important to acknowledge them. Being in a relationship where you consistently feel taken advantage of can be emotionally exhausting.

This Is a Major Red Flag

Will’s behavior, particularly his reaction to paying his share, is a significant red flag. His immediate rage and name-calling (“selfish, childish gold-digger,” “irresponsible and pathetic”) when confronted about his financial responsibility reveals a deeply concerning lack of respect, emotional maturity, and accountability. This goes beyond just money; it speaks to a fundamental imbalance in the relationship and his perception of you.

Focus On Yourself

Given the emotional abuse and disrespect you’ve experienced, your immediate focus should be on your well-being. This means creating space from Will to process what happened and decide what you want for yourself. His lack of apology and continued anger indicate he’s not ready to take responsibility or change.

Consider Ending the Relationship

Based on his consistent pattern of avoiding payment, his manipulative behavior, and especially his furious and abusive reaction when finally made to pay, it’s highly advisable to end this relationship. These actions are not indicative of a healthy, respectful partnership. You deserve someone who values you, treats you as an equal, and contributes fairly to the relationship. His true colors came out when he was inconvenienced, and it was a very ugly display.

You Are Not Wrong

You were not wrong for leaving or for sending him the money with that message. You had been patient for seven months, repeatedly covering his share with false promises. You gave him one last chance on your birthday, and he failed. Your actions were a direct consequence of his long-standing, disrespectful behavior. Your breaking point was valid, and you asserted your boundaries.

Embrace Your Strength and Move Forward

Moving forward, take time for yourself. Reflect on what you truly want in a partner and a relationship, and do not compromise on fundamental respect, fairness, and emotional maturity. This experience, while painful, can be a valuable lesson in recognizing your worth and setting healthy boundaries. You’ve shown incredible strength by standing up for yourself, and that strength will guide you to a more fulfilling future.

If you’ve been in a similar situation or have advice to share, we want to hear from you! Share your story in the comments below. And if you’re curious to read another take on tricky relationship dynamics, check out this article.