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Dark Anecdotes Of A Dating Idealist: When Your Best Friend Is Dating Your Ex

Updated: May 06, 2016 00:24
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It was a 4th of July. I was fresh from spending 2 years in LA and I’d arrived with the promise that my Ex-boyfriend, Bob and I would get back together, except he dumped me instead… Nevertheless, the important ex in this story is a piece of human shit named Henry. Henry and I worked together at a bar and quickly developed a very co-dependent  friendship. We shared a brain and I loved him like family. After a year of cooking me dinners, buying me gifts and giving me the world, it became obvious that Henry was in love with me. I’d dodged the bullet each time I felt he was going to say it, being that he was like a brother to me. But one day, after a visit to the tattoo parlor and copious amounts of Jameson, it happened.

no ragrets

When Henry and I got together we were inseparable, fucking like rabbits, making plans to marry… I’d always been career focused but he changed all the priorities in my life. Its strange to look back and acknowledge what a defining relationship that was.  When someone you’ve made the decision to spend your life with breaks your heart, you never forget it. The loss of myself in him, my life’s plan and, most importantly, the loss of my best friend is what hurt the most. It’s the loneliest I’ve ever felt.

Henry and I had a set of  core friends that we did everything with. My closest friend, Amanda, was one of them.  We drank, partied and tried to mend the shit that teared away at us with drugs, self induced vomiting and weekends in the Hamptons. Maybe sometimes we’re  blind to people’s real intentions because they’ve helped us survive. If I’d paid attention, perhaps I’d seen the signs. Like how loyal she remained to Henry after the breakup and followed him to any  bar he managed, or even how she encouraged me to meet him one day to make amends. 4 years had gone by and it seemed crazy to hold a grudge. He was now her best friend and she was mine. So I forgave him. I was so grateful to her, that I didn’t even think it was strange when they got in a cab together at 5am, though they lived in opposite sides of town.

taxi love 2

So there I was, heart broken once more after seeing Bob and waiting for my best friend to come mend me. She arrived just after the fireworks ended, looking very distraught. She urged me to go somewhere quiet where we could talk, but I encouraged her to call Henry to meet up like old times. We walked to 14th Street, and as I hailed a cab, she blurted: “I slept with Henry!” I felt perplexed,  like when you have that dream that all your teeth fall out and you know  you’ll never be the same. As I cried on the steps of Norwood and she recounted the story, one thing was clear: she was willing to lose me to be with him. I thought I knew the pain of losing a best friend, but this was a layered pain I cannot describe.

So what do you do?  You can’t choose how people live their lives or what number you are on their priority list. You can only choose what you can live with. I couldn’t live with them being together. I couldn’t see myself meeting them for coffee and hanging out.  The reality is that I’m not missing out on anything  by not having them in my life. It’s easy to romanticize  stories like these . I can tell you that I miss  Amanda  whenever I go out to a bar and that I wish most men were as smart as Henry.  I think everyone you meet is meant to reflect the things in you that you could never uncover by yourself. So as fucked up as shit can  get when someone you trust hurts you, the only way to rise above it is to thank them for the lesson they taught you… even if mostly you wish they’d get fucked in the ass by a dildo made of razor blades.


Cover Photo Credit: Mallory Gracenin


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Penelope Hernandez

Penelope Hernandez

Lover of all desserts. Yogi by day, night life connoisseur by night.