I Hooked Up With…My Ex’s Best Friend

So the title of the story kinda says it all, until you read this one Staffer’s hilarious albeit regrettable story. What should she have done? Weigh in and share all about your scandalous sleepovers and regrettable hook-ups. This site is No Exes (No Boys!) Allowed!

Before you denounce me as some kind of heartless harlot when I say I slept with my ex-boyfriend’s best friend, hear me out. It takes two to tango, ladies. Yes, it was a happenstance fueled by too many Rumple Minze shots (never tried these? Don’t start…), yes, the gentleman in question okay’ed (and then some…) the decision, but I still found myself feeling morally icky in the morning.

The scene: 2 a.m. at a dark hole-in-the-wall bar in my ‘hood. I had just come back from a trip abroad and was still in the party-hardy mood, apparently. It was my friend’s birthday and it didn’t take us too long to get bombed. Lo and behold, I ran into my ex-boyfriend’s best friend…who also happened to be my good friend since I’d dated my ex for over two years. We got to talking and then to…er, flirting. Next thing I knew, we were in a cab back to his place.

After a few rounds of ‘Should we’ or ‘Shouldn’t we,’ and him confessing he’d always crushed on me, we decided to go the way of Nike and Just Do It. Granted, I had a really bad break-up and relationship with the ex in question, but I feel like this situation was more of one of those ‘Oops! Accidentally hooked up with my best guy friend’ ones. I didn’t do it for revenge, and my ex and I had called it splits six months back.

Either way, I was so embarrassed and upset in the morning that I tried to actually, literally escape—until I realized that my hook-up lived in the basement and the windows were far too small to creep out. I still attempted a stealth getaway, but he stopped me as I was running up the stairs. He drove me home, like a friend would…but that ‘friendship’ hasn’t been the same ever since. It’s been years now and I still wonder if my ex ever found out. Did I do it because he was so, ummm, familiar? Did I have feelings for my ex at the time? I still feel bad—lesson learned.

GIRL TALK TIME: Have you ever had a sleepover with a person you probably shouldn’t have? Who was it? How did it end? What do you think of this story? Was her decision totally wrong or was it okay since they’d been broken up for a while? Like we said, let it out! We’re here to help, not to judge.

26 Comments

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  • Lisette Caesar:

    I dated a friend of my ex for almost a year. It was very weird at first but we handled it like grown ups.

    {Reply}
  • Elizabeth Capobianco:

    No friggin way not acceptable, i dont care how long they are apart for!!!!

    {Reply}
  • Crispy:

    hmm

    {Reply}
  • Stephanie Price:

    friends of exes off limits

    {Reply}
  • Toanya Kesse:

    That kind of stuff happens… Sometimes you have this too familiar kind of thing with someone you might have hooked up with had you met under different circumstances. Sometimes they work, other times you feel like a sleaze.

    {Reply}
  • Shirley Talabert:

    whaaa! that’s crazy

    {Reply}
  • avatar
    Jackie:

    Should never go there with anyones ex.

    {Reply}
  • avatar
    FreeCee:

    IMO, people should stop using alcohol as an excuse for their behavior. I personally consider friends of exes off limits but I won’t knock someone that feels differently.

    {Reply}
  • Nina:

    It will be him and your little secret ;)

    {Reply}
  • avatar
    Dolores Sperling:

    SHOCKING

    {Reply}
  • avatar
    Dolores Sperling:

    INTENSE

    {Reply}
  • Shirley Talabert:

    whaaa! that’s crazy

    {Reply}
  • avatar
    Melissa Kreinin:

    oyyy sticky situtation..

    {Reply}
  • Cynthiapp:

    I feel you did exactly what you wanted to do ….we all have choices! ……and then you felt bad about it afterwards…….what was that really about?..hmmmm

    {Reply}
  • Shecky's:

    While we always appreciate hearing from you on Sheckys.com, your comment has been removed. We’re keeping the new Sheckys.com a safe and respectful place for all of our girlfriends and we need you to help us reinforce that mission.
    Thanks again for being a user.”

    {Reply}
  • avatar
    Tammy Aramian:

    Regrets, yes, but live and learn. All’s well unless you got an STD or pregnant!

    {Reply}
  • Diamondeva:

    I can totally relate…I MARRIED my ex’s best friend. THAT ended in disaster. I wouldn’t recommend it, but don’t feel too bad. Apparently it is not that uncommon of a situation.

    {Reply}
  • elle:

    this is normal, no need to feel like it was a regrettable mistake! plus, the only person who’d say that friends of her ex are off limits, means that her exes friends aren’t HOT!

    {Reply}
  • avatar
    jenny-o:

    i think you were fine. things happen.

    {Reply}
  • Joy:

    A few regrets but can’t live in the past and let it get to you. They are life lessons to make you better.

    {Reply}

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