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Breaking Up Is (So) Hard To Do


Have you endured an awful bust-up? Find solace in these true tales of just how badly love can hurt.

By Chelsea Kaplan

ven under the most amiable of circumstances, ending a romance is pretty crummy. But when the big good-bye is compounded by a hearty dose of mortification, jealousy, and nastiness—well, it can be enough to make you want to swear off dating forever. But don’t! These tales from the trenches may just make your own breakup seem like a walk in the park! These folks lived to love again—and so will you.

No fireworks
“My boyfriend Charlie asked me to meet his family for the first time at a huge Fourth of July party his parents had every year at their home in
I received a letter breaking off the engagement, written by her mother!
Seattle. In the weeks leading up to the party, we had been squabbling, but I thought that the arguments were nothing to worry about. As we boarded the plane, we got into a fight over who was going to sit in the aisle seat. In the middle of the fight, he blew up and said, ‘Christy, this isn’t working at all. I can’t do this anymore—we have to break up.’ I had to sit through a cross-country flight with him, not to mention a weekend in Seattle with his family, knowing full well that our relationship was over. Needless to say, it was one of the worst holidays of my life!”
—Christy Alvarez, Charlotte, NC

See ya later, neighbor
“The summer after I graduated from college, I got an internship in Los Angeles and found a great three-month sublet. Soon after moving in, I started dating my neighbor. But upon realizing she was the insanely jealous type, I broke up with her. For the rest of the summer, she made my life nightmare—she’d scream obnoxious things at my door when she knew I had a date over, and she even put up signs in the hall and in the building’s elevator falsely saying that I had a venereal disease! It was a miserable experience—so bad that after the summer was over, I packed up and left L.A. for good.”
—Matt Yancey, Rancho Santa Fe, CA

Don’t save the date
“When I was 28, I met a Venezuelan girl who was spending a year working in New York. We had a whirlwind romance and got engaged on Valentine’s Day after having dated for five months. Shortly after the engagement, we began making wedding plans to be married over Labor Day weekend in Venezuela. She headed home in June to finalize some wedding plans, but after two weeks, I didn’t hear from her. After three weeks had gone by, I received a letter breaking off the engagement, stating little more than that the wedding was called off and that she’d be returning the ring. As if that wasn’t bad enough, the letter was written by her mother! Lesson learned: It’s probably a good idea to get to know a person a little longer than five months before buying a ring!”
—Nathan Koort, Spring Lake, NJ

Easier over email?
“I used to work in college admissions, so to please my then-boyfriend Gregg, I agreed to help his extremely difficult daughter with her college applications, even agreeing to take her on college visits over the summer. I began noticing that Gregg kept canceling our dates, yet not canceling any that involved my coming over to his house to help his daughter. A week before we were set to depart for our trip, she sent me an email saying that that her dad no longer wanted to see me, but that she hoped I would still agree to take her on the trip. I quickly wised up to the fact that he was totally using me, and I made the decision to go to the beach with my friends instead of going to visit college towns!”
—Staci Patterson, Wilkes-Barre, PA

Cleaning house
“My girlfriend and I had been living together for three months when one evening I came home from work one summer night and all of her stuff had been moved out of our apartment—everything down to her
I’ve vowed to never live with a woman until we’re married.
shampoo in the shower! I thought it was some sort of practical joke. After finally getting a hold of her on her on her cell phone to ask what the heck was going on, she fessed up that she had been having an affair with another guy and was moving in with him. Ever since then, I’ve vowed to never live with a woman until we’re married.”
—Will Sussman, New York, NY

A picture speaks a thousand words
“During end-of-year festivities when I was a senior in college, I went with my girlfriends to Padre Island, TX, and my boyfriend went with his pals to Florida. On the last evening of the vacation, I received a photo message on my phone of my boyfriend kissing a girl I knew he always had a crush on, with the text under the photo reading ‘See ya later, Dana!’ I imagine what happened is that he meant to send the message to his best friend Dave, but instead sent it to me, probably because my name, Dana, was alphabetically listed above Dave’s on his cell phone. I’ll never know for sure, because I refused to speak to him after that.”
—Dana Tillert, Shaker Heights, OH

A colorful breakup
“I always thought that Shawn, the girl who colored my hair, was incredibly hot. I finally got the nerve to ask her out, and we dated for about four months. After getting to know her better, I realized she wasn’t for me, so at the end of summer I ended things. I thought the breakup was completely amicable; she seemed totally understanding, and I was so happy when she told me to keep my hair color appointment I had for the following week. When I arrived at the salon, she was chatty and smiling, so I felt like everything was going to be fine. After the shampoo girl rinsed the dye out of my hair and wheeled me in front of the mirror, I saw that my hair was fire-engine red instead of dark brown. Apparently, she wasn’t as cool with the breakup as I thought she was.”
—Paul Ostrofsky, Mansfield, TX


Writer and editor Chelsea Kaplan's work has been featured in Men's Health, New Woman, Bridal Guide, The Mommy Times, and The Family Groove.
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