I Tried To Make My Best Friend Dump Her Boyfriend

Yes, it’s true: I tried to make my best friend dump her boyfriend. I already know what you’re thinking: How could she try to ruin her best friend’s relationship? Friends are supposed to support each other! They’re supposed to love each other! They’re supposed to be happy for their friends when their friends are happy!

And, you know what? You’re right. You’re totally and utterly right. That’s what good friends do. But, in my defense, that’s exactly what I was trying to do… in my own way.

Let me explain. It all started three years ago with a holiday to Orlando, Florida. Wait, no — that’s a lie. It all started seven years ago with a bet, a kiss, a princess, and a monster. The princess in this story, of course, is my best friend — let’s call her Jessie. The monster is the evil boyfriend — let’s call him John. And the bet? Well, it took place in a dingy dungeon (i.e. a nightclub), when John’s companions put a wager on whether or not John could steal a kiss from the fair maiden! John lured the fair maiden in, naive and brimming with hope, and stole that kiss.

But all fairy tales aside, this wasn’t exactly your typical recipe for a whirlwind romance. And, in fairness, if Jessie had known about the bet, things very well may have turned out differently. I think we can all agree that the bet was a cheap, vulgar, and disrespectful way to approach a woman, but at least it paints an accurate picture of what kind of guy we’re talking about here, right?

John is an absolute jerk, but it’s kind of run-of-the-mill jerk, so far. I can say this because I knew John already. In fact, I worked with him — more specifically, he was my supervisor. Even more specifically, he was a supervisor that I already disliked.

You see, John is the type of sleaze that seems to develop over time. At first he just feels sort of “off”, emanating a kind of vaguely offensive sleaze that a lot of guys have because they don’t know how to function in any genuine and heartfelt way. But over time, he got worse; his stares, smirks and shrugs aimed to wound and his comments aimed to kill. He was poison to anyone naive enough to get close to him. And, of course, Jessie was just his type of naive. She was younger than him, and eager to please.  And John? Well, he had caught his prey.

And while Jessie knew I wasn’t John’s biggest fan, she loved him, and even after their rocky start, she seemed happy. How can you begrudge your friends their choice in partner, right? So I sat on my feelings and opinions. I didn’t tell her how I really felt about him. The years dragged on, and I accepted him into my life, if not as a friend, then as a person that was dearly loved by a good friend of mine and that I would have to learn to get along with.

That is, until my own boyfriend at the time (let’s call him Mark) and I went on a summer vacation with Jessie and John. As Jessie and I are huge Harry Potter fans, we were just dying to go to Universal Studios in Orlando, Florida to see the new Harry Potter area. We were unbelievably excited.

The holiday started off amazingly, mostly because Mark and I arrived a day early and John wasn’t there to ruin it yet. When they landed, I saw him bounding up to us with his long lanky legs, neon orange shoes and a matching t-shirt. He had lost weight — a lot of weight — and he walked with an extra dash of arrogance I didn’t think possible. Something inside of me shuddered. But Jessie was, as always, bubbly and cheerful. I didn’t suspect a thing.

But that didn’t last long. As the holiday wore on, I started to notice cracks in their relationship. Jessie and I would go shopping and she would tell me she wants to get something sexy to wear for John. “Fine!” I’d say, “That’s always a fun to do things like that with your partner!” But when I asked (in all girl-confidentiality, of course) how the lingerie went down with John, she responded with an uncharacteristic sigh and frown.

Jessie started to open up more after that and explained that they had been fighting a lot lately, but that she thought things were getting better. I, on the other hand, thought it was getting worse. John’s behavior was getting stranger. Every single day, at about the same time, he would disappear for hours to call his parents back home. Which would be fine, if he wasn’t a 27-year-old man working a professional job who wasn’t that close to his parents in the first place. Then at night he’d would make snide comments at the food that Jessie was eating, or the amount of alcohol I was drinking. We were all lesser in his eyes, and we felt him tainting every aspect of our holiday.

Then one evening, Jessie asked me to do her makeup for her, and I did. It was the whole sex bomb look, and she rocked it. But still, he looked the other way. That’s when she confessed to me that he wouldn’t share her bed. They had been together over four years, and they were no longer sharing a bed.

That was it for me — I couldn’t take it any longer. I started to heavily drop hints to Jessie that she should break up with him. I started to be brutal, to paint him in the light that I saw him. I started to encourage her to hate him. But I was also working bolster her confidence. She didn’t think she could do any better, so I needed her to see that she could. We bought her new clothes, I pointed out when men were looking at her, and I tried to show her how wonderful she was. By the end of the holiday, I was basically saying the words: “I wish you’d just break up with him, before he breaks up with you.”

When we got home, I was racked with guilt. I wasn’t sure if it was my own feelings of him that were clouding my experience of their relationship on the holiday. I started to think that I should have been more supportive of the relationship. But my doubts didn’t last long. Only three days after we landed, Jessie got a phone call from John just 15 minutes before her shift in work started asking if he could talk to her. She text me and let me know he was coming by to talk, and that she was hopeful that he wanted to try and mend things.

But I already knew. He had beat her to the mark. He was about to break her heart. I stood by the phone, car keys in hand, waiting to hear from her, and waiting to help her pick up the pieces.

Fast forward to one year later, and John’s married to another woman. Specifically, to the other woman those phone calls “home” were to. He had been cheating on Jessie for well over a year, had actually introduced Jessie to her. According to him, he wanted to break up with Jessie sooner, but he had really wanted to go on the holiday to Orlando. Poor sod.

Now, when I look back at our time in Orlando, I wish I had tried harder. I wish I had seen more. I wish I had been more willing to screw what society says a friend should be and do. I should’ve listened to my gut, and to hell with what everyone else thought.

I should’ve broken my best friend and her boyfriend up.

Sarah is a full-time content marketer, part-time freelancer. She’s a serial hobbyist (which just means that she does a lot of random things, but none of them particularly well). Her real talent lies in her ability to consume copious amounts of wine, whilst discussing feminism and reading A Song of Ice and Fire for the 8th time... All while saving puppies from burning houses, of course. You can see more of her work here, or pop over to Twitter and say “‘ello ‘ello” @daughterdipstik