I, F(20), have been best friends with a guy we’ll call Rocco, M(20), for the past eight years. We’ve been inseparable since middle school. Throughout our friendship, there’s been a pattern of him developing feelings for me, confessing them, and me having to gently turn him down. I’ve always made it clear that I’m not interested in him romantically. I love him like family.
About a week ago, Rocco and I were on FaceTime playing Roblox like the mature 20 year olds we are. At one point, he went upstairs to grab a snack. While he was gone, his older brother, M(26), who we’ll call Derrick, grabbed his phone and said, “Hi, so when are we gonna hang out?”
For context, Derrick and I were never close. He knew about Rocco’s feelings for me, and he lives full time in another state. I awkwardly laughed and replied, “Soon,” then asked how Colorado had been. That was it before Rocco came back downstairs.
Later, Derrick DM’d me on Instagram asking me to tell Rocco to hang out with him. I immediately told Rocco, who laughed and said, “I don’t want to hang out right now.” I relayed the message back.
That’s when Derrick started making sarcastic jokes about stealing Rocco’s car and crashing it because he wouldn’t hang out. I jokingly replied, “I’ll bring the knife to slash the tires,” playing along.
Out of nowhere, Derrick asked for my address so he could pick me up. Still thinking it was a joke, I gave it to him.
Ten minutes later, Rocco’s car pulled up outside my house.
Rocco and I were still on FaceTime, so I knew it wasn’t him driving. I pointed the camera at the window and said, “Look who’s at my house.” Rocco saw Derrick sitting outside waiting for me and immediately got upset and hung up. Apparently they’d already had issues with Derrick taking his car.
I was shocked Derrick had actually shown up, but I still walked outside. I told him, “I didn’t know you were serious.”
He laughed and told me to get in.
Like the dumb 20 year old I apparently am, I did.
He started driving toward his and Rocco’s house, saying we were going to pick Rocco up. I was excited because I thought the three of us were just going to hang out together. On the drive, Derrick and I started genuinely talking for the first time. He opened up about his ex fiancée and life after their breakup.
When we got to Rocco’s house, we told him to come outside. He immediately started yelling at Derrick to turn around and take me home. He demanded his car back and was furious.
Derrick and I both tried calming him down, but Rocco was adamant that Derrick never should’ve taken his car and that I needed to go home.
Eventually Derrick drove away, lit a cigarette, and handed it to me like we’d known each other forever.
That’s when things shifted.
For the next hour, he drove us around while we talked about our lives and relationships. The conversation flowed effortlessly. At one point, he suddenly pulled over and told me to switch into the driver’s seat instead.
The whole thing felt weirdly cinematic after that. Windows down, music blasting, and every now and then I’d catch him staring at me with this intense look.
When we got back to my driveway, the energy felt completely different.
We got out to switch seats again, and Derrick motioned for a hug. It caught me off guard because we were still basically strangers, but I hugged him anyway. He pulled me close, and suddenly his hands slid under my shirt onto my lower back near my bra strap.
I was shocked. Part of me knew I shouldn’t be going along with any of this, but another part of me felt drawn to the spontaneity and excitement of it all.
I looked up at him while we were hugging, and he gave me that look guys give right before they kiss you. Then he leaned down and kissed me.
What started as one kiss quickly turned into a full makeout session, and I could tell he wanted things to go further. The second I sensed that shift, I pushed him back.
He asked, “Should we go somewhere else so we’re not in front of your family’s house?”
Completely flustered, I replied, “Before anything like that ever happens, you need to tell Rocco about this, and you need to take me on a date.”
He smirked, nodded, and agreed.
Ever since then, he’s called me almost every night, but only between midnight and 3 a.m., and every conversation turns into him trying to hook up. There’s been no mention of the date he promised or any sign he plans on telling Rocco.
At one point, I flat out told him I would never see him again if he didn’t tell Rocco the truth. I also made it clear that I’m not someone who does hookups. I date for marriage.
He brushed it off and said Rocco is “sensitive” and that he needed to make sure he was really into me before telling him anything.
Eventually, I decided to tell Rocco everything myself.
Rocco did not take it well. He completely cut me off.
To make matters worse, Derrick has twisted the story to make it seem like I’m the one who pursued him, called him constantly, and wanted to hide everything from Rocco. Derrick, a grown 26 year old man, has even told his mom that I’m harassing him despite the fact I haven’t reached out to him once.
And Rocco believes every word of it.
So now I’m left wondering: am I the asshole for kissing my best friend’s brother, even though I eventually came clean and took accountability for it?