Man Says He Dumped His Girlfriend After She Gave Him a ‘Hall Pass’ to Sleep with His Old Crush

A 24-year-old man turned to Reddit for advice after a breakup that left him questioning his entire relationship.

He explained that he ended things with his girlfriend after she unexpectedly gave him a “hall pass” — permission to sleep with an old crush.

“A while ago, an old friend (F23) from my school days, Lana (fake name), reached out to me on Instagram,” he wrote. “I had a crush on Lana when we were at school, but nothing ever came of it — we just remained friends.” He said Lana had since moved across the country but mentioned she’d be visiting his city and wanted to catch up.

At first, he thought it was innocent. “I didn’t mind the idea of catching up with Lana; we were good friends,” he said, noting that he was honest about being in a relationship. Out of respect, he asked Lana if he could bring his girlfriend along — and she agreed.

That’s when things took an unexpected turn. “I ask my girlfriend if she wants to come, but she recognizes Lana’s name and remembers I had a crush on her,” he wrote. Instead of being jealous, his girlfriend made an offer that completely unsettled him.

“This is when things get weird,” he wrote. “My girlfriend asks why I invited her too and why I don’t just go with Lana alone. Then, out of the blue, she offers me a ‘hall pass’ to see if I can get Lana to sleep with me.”

At first, he laughed it off, assuming it was a joke — but she was serious. “My girlfriend is not only giving me permission, but she wants me to try and sleep with this girl… a girl that I had a crush on about 10 years ago and haven’t seen in seven.”

The offer left him deeply uneasy. “I’m really weirded out by this,” he said. “I asked her why on earth she’d offer me something like that, and she just said, ‘Well, don’t you want to?’ ”

He couldn’t stop thinking about it. “It messed with my head the next day,” he admitted. “Was it a test to see if I’d cheat? A kink she never told me about? Did she cheat on me and feel guilty? Or was she planning to cheat and wanted me to ‘cheat’ first?”

When he pressed her for answers, she remained vague. “She just said, ‘Well, you had a crush on her, didn’t you?’ ” he recalled. The lack of clarity only made him more suspicious. “I couldn’t shake the feeling she was testing me — or hiding something.”

Ultimately, the confusion and mistrust were too much. “In the end, it messed with my head enough that I decided to break up with her,” he wrote.

Not everyone agreed with his decision. “My friend thinks I’m an a—— for dumping her,” he shared, adding that his friend called him “lucky” to have a girlfriend willing to let him sleep with others. But to him, the issue wasn’t about freedom — it was about trust, and that trust was gone.

“I think you just discovered you and your girlfriend aren’t compatible on some level,” one commenter wrote. “She’s okay with something you’re not, and that’s reason enough to walk away.”

Another added, “Maybe she’s insecure and doesn’t trust you. She could be giving you the hall pass so it wouldn’t count as cheating — a way to keep control while convincing herself she wouldn’t lose you.”