A 23-year-old woman decided to flirt with her male roommate during D&D night, thinking he’d never reciprocate her feelings. The next day, he knocked on her door asking if she’d ever thought about him romantically, and her roommate flirting confession went completely sideways.
The Backstory
Our protagonist lives with a 21-year-old guy she’s been secretly in love with since June. They’re both bisexual and part of a friend group where everyone flirts with each other constantly. She calls him her “gay boyfriend” and he calls her his “lesbian girlfriend.”
They have regular D&D nights with their friends where alcohol flows and the flirting gets even more intense. She figured this was the perfect cover to express her real feelings without consequences.
After all, he didn’t like her back, right? What could possibly go wrong with a little harmless flirting during game night?
The Incident
During their latest D&D session, she decided to amp up her usual flirting with her roommate. Nothing too obvious, just enough to satisfy her own feelings while keeping it “jokey” enough to maintain plausible deniability.
The night went smoothly. Everyone laughed, drank, and played without anyone feeling uncomfortable. The car ride home was quiet, but she didn’t think much of it.
Then came the next evening. She was reading in her room when he knocked on her door, getting ready to leave for work. He asked the question that sent her into a complete spiral: “Have you ever thought about me in a romantic sense?”
She immediately panicked and blurted out “no.” Then her brain caught up and she backtracked: “Well that’s a lie, I have but I understand if you don’t feel the same and I’ll back off.”
Right then, his work alarm went off. He had to leave before he could respond, leaving her alone with her thoughts and regrets about the roommate flirting confession disaster.
What Reddit Said
Most people were surprisingly optimistic about the situation. They praised the roommate’s direct communication style and encouraged her to pursue the conversation when he got back from work.
Some commenters pointed out that his question suggested he might have feelings too. Why else would he bring up romance after their flirting session?
A few skeptical users questioned whether the story was real. They found the timing of his alarm going off right after her confession suspiciously convenient, like something from a romantic comedy script.
Others focused on practical advice about how to handle living together if things went badly. They reminded her that six months left on a lease could feel like forever with the wrong roommate dynamic.
The Verdict
This wasn’t really a case of anyone being wrong, just two people finally addressing feelings that had been building up. The roommate flirting confession might have been awkward, but it opened a door that needed opening.
Her panic response was understandable, but his direct question suggests he’s interested in exploring something real. The fact that he brought it up at all shows he’s been thinking about their dynamic too.
This is exactly the kind of relationship drama that makes living situations complicated, but sometimes the best connections come from the most unexpected places. Whether you’re dealing with AITA stories or roommate confessions, honest communication usually beats awkward avoidance.
From r/tifu (1,211 upvotes)