I Slept With My Brother’s Best Friend & It Ruined Their Friendship

There’s such a thing as girl code and even bro code, but typically there aren’t any rules about sleeping with your sibling’s friends. My brother’s best friend was nerdy, dirty, and so much fun, so I just couldn’t say no when the opportunity to sleep with him arose. It completely ruined their friendship and I feel a little bad about it, but not bad enough that I wouldn’t do it again.

  1. Sometimes it’s fate. Sometimes a weird chance encounter leads to something life-changing. That’s exactly what this was. I met my brother’s best friend randomly at the bar and we hit it off. He was so nerdy; we talked about spreadsheets and Marvel comics for ages. He was nice and dirty as well and our conversations eventually turned sexual—the chemistry was undeniable.
  2. We fooled around the first night. I didn’t sleep with him that first night, but we got home late and fooled around like teenagers in my driveway. I felt alive! Remember the butterflies you’d get when you were a kid doing something you knew you shouldn’t? It was exactly like that. It started off innocently enough; I added him on social media and finally I gave him my phone number. We’d stay up all night talking and text all through the next day. Our relationship was definitely growing into something more than just a one-night stand.
  3. I didn’t tell my brother. We agreed early on to keep things quiet because he didn’t want it to get weird for him and my brother. My perspective was that we were all adults and it only had to get weird if we let it. In the spirit of compromise, I promised not to say anything.
  4. Things quickly escalated into blow jobs in the Target parking lot. The first time I went down on him was in the parking lot of Target. We went in for contact solution and came out with our hands all over each other. I teased him by “accidentally” dropping my phone on the driver side floor and leaned over him to get it. One thing led to another and I ended up with his junk in my mouth. Best Target trip of his life.
  5. We couldn’t ever go to my house. I didn’t want to leave any evidence of him being at the house because my brother lived only two blocks away. I didn’t want someone to see his car in the driveway, so we’d always park somewhere else and fool around in the car. We’d scope out the darkest parking lots where we were sure we wouldn’t be seen. It was all very dramatic. (Volkswagon Jettas have a super spacious back seat if anyone was wondering—perfect for a 6’3″ guy to get the right leverage against the door.)
  6. One drunken night ruined everything. We went to a bar on the outside of town and drank way more than we should have. Of course my hands were on him all night, teasing, playing, flirting… We took a ton of selfies of us hanging all over each other before paying our tab and heading back to his place.
  7. The sex was so good, you guys. That night was definitely in the Top 5 sexual experiences I’ve ever had. Anything and everything we could possibly do to and with each other, we did. And we took more pictures—lots of raunchy ones, in fact—to remember the night. After a few hours of jungle sex, we were both sober enough to drive and he took me back to my car.
  8. Pictures are never a good idea. If you’re ever considering pictures, make sure you take them on your phone, not your partner’s. A few days later while my fling was out with his boys (including my brother), the phone was unlocked and our pictures were seen by everyone in all their glory. Oops?
  9. My brother was mad at both of us. My brother didn’t see everything, but he saw enough to know that we had sex and had been talking behind his back for over a month. My fling screwed me over shortly after we were outed, and that was the nail in the coffin of their friendship. I cried for days to my brother about how awful his friend was. It’s one thing to screw me, it’s something totally different to screw me over. That being said, the sex was so good I’d do it all over again even one more time if no one would find out…
Mom. Ex-wife. New on Tinder & figuring out the new dating rules all these years later.