Diary of a 20-Year-Old Breakup Procrastinator

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Photo: Petrified Collection/Getty Images

Breakups aren't typically the times we show our best selves. But in my personal experience, the lead-up to a breakup can be just as bad. Very few people realize something isn’t working and dump their partner that minute; they sit on it for a bit. Some people — like me, for most of my 20s — would sit on it for as long as possible (once, spending almost an entire relationship in a state of wanting to break up). It undoubtedly sucked for everyone involved.

What follows isn’t a real excerpt from my diary, but a fictionalized version of how bad it can get.

8/24

Dear Diary,

I couldn't break up with her tonight. She wanted to come over to my place. A few months ago, Mikey told me you can't break up with someone at your place, because then you can't leave afterwards and you just break up over and over for hours. That sounds like torture.

8/26

Dear Diary,

She made Labor Day plans for us, so I guess we aren't going to break up wearing white. It's probably for the best. What if I showed up at her place — totes ready to break up — and she were wearing a wedding dress? Then when I bounce, she'll, of course, start drinking red wine straight from the bottle to numb the pain and likely stain the dress. I can't deal with that burden. Do you know how much wedding dresses cost? I don’t, because I'M NOT GETTING MARRIED FOR, LIKE, ONE MILLION YEARS. But I think they're pricey — like $800.

 8/28

Dear Diary,

I was going to do it, but before I could say anything, she asked, "Is everything okay?" I said, "Yeah. Totally. Definitely." Who has three thumbs, is okay, and is lying about the amount of thumbs he has? This guy!

9/3

Dear Diary,

It was a pretty nice weekend. We went to this party where everyone was supposed to wear linen. I didn't know that was a type of fabric, so I just wore a towel over my waist and a fitted sheet as a cape/shawl. My girlfriend told me to wear her big floppy hat and act like I was being ironic. It totally worked.

9/4

Dear Diary,

Forget what you heard, I'm definitely breaking up with her. Today, she sent me a viral video. The email should've been subjected "here's a video of a baby eating cereal for the first time; we officially have nothing left to say to each other."

9/5

Dear Diary,

I couldn't break up with her tonight. I was thinking it's a bit too close to September 11. You need a few buffer days. If I did it beforehand, I'd put her in an awkward position. Like, it would be the 11th and she'd be crying on a bench because it reminded her of when we once saw a bench, but people will think it's because of 9/11 and they'll come up to her to commiserate, forcing her to either lie about the impact 9/11 had on her or seem like a narcissist with no perspective.

9/17

Dear Diary,

I couldn't break up with her tonight. We were eating at my favorite local and she didn't like her scallops. Breaking up with her then felt like pouring salt on her scallops that she already found to be a bit salty.

9/22

Dear Diary,

I was going to break up with my girlfriend today, but then I realized it was the last day of summer. I didn’t want her to say, "This is just because it's the end of summer, isn't it? Like you felt it was some sign from Mother Nature. Grow up!"

10/01

Dear Diary,

Did you know that some people pick their Halloween costume every year on October 1? Like it's a ritual? Anyway, my girlfriend already bought our couple's costumes. We're going as Michael Jackson's hands. I guess it's cool that I get to be the glove.

10/30

Dear Diary,

I almost broke up with my girlfriend last night. Then I pictured the tragic image of her walking around as Michael Jackson's dead left hand. She'd have to explain what happened all night. I'm too good of a guy to do that to her.

11/4

Dear Diary,

We're going to my parents' place for Thanksgiving and her place for Christmas. It makes sense, she explained, because I'm Jewish, so it's not like I have a Christmas tradition with my family. I was going to tell her that at least General Tso was a real person — unlike that creep Santa — but then I got hungry and we ordered Chinese food.

1/1

Dear Diary,

Okay! New Year — new life. I am definitely going to break up with my girlfriend tonight. I almost did it last night, but I didn't want her to not have a midnight kiss. She loves When Harry Met Sally. Or at least that's what she said the third time I made her watch it. Oooh, maybe she'll want to come over tonight to watch When Harry Met Sally. We can order Chinese food. I'll break up with her later in the week or whatever.

1/2

Dear Diary,

My girlfriend broke up with me. She says I've been distant and weird. I don't know what she's talking about.