People Share the Times They Truly Sucked at Breaking Up with Someone

It's difficult enough to come to the decision to end a relationship—even more difficult to find a way to end things amicably and with respect for both parties. Even in those rare cases where everything seems bizarrely normal and okay, you still may wake up one morning to find your cat missing or discover that your partner's strongest quality is their aptitude for unflinching denial. We asked asked friends to tell us those awkward times they failed at breaking up with someone.

I really wanted to break up with my ex-boyfriend for a long time, but I was sad and nervous and knew it would devastate him. One night, I decided I couldn't stand it anymore and had to do it; I had made out with our friend at a club a couple of times and it was just clear that I was being unfair and needed to not date anyone at that point. I decided I was going to do it the next morning.

I got up and psyched myself up for it, but then when I came back into the bedroom to see if he'd woken up, he initiated sex with me. As part of the deterioration of our relationship, I had developed a real aversion to sex of any kind, so I felt guilty about this and initially just went along with it. He started going down on me; at first I was laughing, going along with it, and then I started crying a little bit (which I don't think he noticed). When he finished I blurted out, "I want to break up!"

I broke up with my boyfriend after we had met up for froyo. Then I rushed outside because I felt so awkward and proceeded to ram my car into his parked car. We had to wait and sit for the police to come to file a report. Then I had to drive him home.

I broke up with my boyfriend of a couple years very amicably. We lived together and had to split up our things. It seemed a little bit too easy when he told me that I could keep our cat, which he adores. He ended up stealing my cat and moving to another state.

I had dated this guy for a while and wasn't feeling it. He didn't get the message and would continue to call me. If that wasn't bad, he started to randomly show up at places that I would go.

One day, I walked into the coffee shop where I worked and saw him waiting for me behind the counter. He thought that some nice quality bonding time would bring me back to him. So naturally he applied to be at a barista at my work. He also told the owners that we got along great and that I would love to work shifts with him.

I told her we weren't going to be together anymore over some frozen custard. After I asked if we were cool, she reached out and grabbed my ice cream cone and threw it on the floor.

I broke up with a girl over the phone, but after that we had to have a weird back and forth about me returning a copy of Iron Man to Blockbuster. It started with an email:

Re: Iron Man

Hey Jack,

I went to Blockbuster yesterday and it seems the copy of Iron Man we rented hasn't been returned. Can you please take care of this?

So I had to dig it up, and then I had a long internal debate over whether or not to just pretend I couldn't find it. But I wanted my emotional scarring karma to be low, so I found it, biked over, and paid the fee. We didn't talk or see each other for three years after that.

I broke up with a girlfriend for my current girlfriend. She seemed to take the break-up well, and I hadn't heard from her in weeks until one night when I heard my doorbell ring. Before I got outside, I heard sprinting, a car door slam, and wheels screeching. There was trash all over my yard. Upon further inspection, I saw that someone put silly string on the brake pads of the car parked outside and completely covered it in Saran wrap. There was also a baseball bat-sized dent on the back of the car.

It would have been just annoying but it wasn't my car; I had to pay for my little brother's friend's car to get fixed.

*Names have been changed.