Page 1 of Lessons in Heartbreak

Chapter OneRuby

Despite the fact that worst-case-scenario thinking was my default state of mind, I never could have guessed that my friend’s gift of a monster sex toy would kick off the most dramatic series of relationship events I’d ever experienced.

It wasn’t the sex toy, per se. How could it be? Not that it wasn’t dramatic, of course. That thing had more bells and whistles than most of the electronics in my possession.

It was more what it represented.

Because the first thing I felt when I laid eyes on it—buried underneath tasteful wrapping paper and a beautiful shiny bow—was pure, unadulterated terror.

How was anyone supposed to slip under their sheets—mine, in this instance, were high thread count, with a cute little-blue-flower print—spread their legs for a giant rotating, vibrating thing with appendages, and feel even the slightest bit relaxed?

In truth, this was a me problem. Lauren was great, as was her gift-giving ability. There was an element of thoughtfulness to this terrifying gift that I wasn’t quite ready to see. It stemmed, of course, from our repeated conversations about my lone sexual experience and how I wasseemingly incapable of creating more experiences—betterexperiences—to wipe that one out.

The longer I went without those more frequent and better experiences, the harder it became to put forth the slightest effort. Now I had the strongest notion that when my gynecologist asked me to spread my legs for my next exam, a stray moth might fly out.

It wasn’t that I didn’t want to try. Not really. But letting someone in—to me—was as scary as jumping out of a plane with no parachute.

I know, I know ...control freakwas right aboveworst-case-scenario thinkingon my list of personality traits.

The hardest part about being a control freak was admitting it, and it took me until my thirtieth year to be able to do so. And here’s what makes it so hard to admit—when you struggle with control issues, especially as a younger person, most people look at you in such a positive light.

My parents were constantly told things like,Oh, she’s such an old soul.

Ruby never causes any trouble, does she?

You’re so lucky. She’s such a serious little thing. You must never have to worry about her.

But you know what that really meant? It meant I took on about a hundred times more responsibility than I should have at a young age. It meant that I was juggling mental weight that was far too heavy for someone in my age bracket.

Old soulwas just another way of sayingcan’t relax enough to express their emotions.

And as I got older, that positive reinforcement just kept on coming in.

I was responsible. Organized. Motivated. High-achieving.

That list showed up in so many places in my life: In my grades. My extracurricular activities. The complete and utter lack of a social life. While most kids in high school were going to football games andgetting asked on dates, experimenting with their sexuality and hooking up with harmlessly inappropriate peers, I was locked away in my room, doing homework and reading and making sure that every single domino was lined up to get all the things I wanted out of life.

Valedictorian? Check.

Student body president? Check.

Debate team, yearbook staff, event planning–committee chair—the list went on and on.

To no one’s surprise, my parents ate all this up. It was the clear benefit of being the only child of two high-achieving people. They were the ones who wanted to keep every test marked with an A, the ones who loved hearing about any project I was working on; who happily encouraged me to take on more responsibility, to volunteer for more committees because it would look great on a college application. Achievements were the way we related most.

Was I doing all the right things at the right time? Check, check, check.

Ours wasn’t a relationship based on deep, emotional talks, but more of a “Look at this bright, shiny thing I’m bringing home!” declaration. They loved those little trophies, real and unseen. And oh, it was how I’d always felt the most loved. The discussions about books and the deeper themes found in the text; the pulling apart of the things we all read, the things they taught in their respective college courses—my mom was a statistics professor, my dad a lit professor, both tenured at Colorado State University in Fort Collins.

Because of that, college wasn’t as heavy on the extracurricular, and instead of living in the dorms to get the messy experience there—I could do without the great social experiment, thank you very much—I chose the safer, much more practical option of commuting. They supported the choice because it was responsible. It was financially smart. It was prudent.

Just what every twenty-year-old girl likes to be called.Prudent.

Believe me, I still got the college experience. The number of hungover frat boys who tried to cheat off my papers in class was truly staggering.

But I was consistent. I always got good grades. There was no stumbling in late at night or tripping into class with bleary eyes and two-day-old mascara. It never bothered me back then because I was admired by my peers, my professors, and my parents.

It wasn’t until later that there was a creeping sense that maybe something wasn’t quite right.

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