After a particularly soul-crushing breakup in college, I found myself in the Self Help section of Barnes and Noble. 

In a sea of bright, happy covers designed to lift my mood on sight, the vaguely vintage look of All The Rules caught my eye. All The Rules promised a step-by-step guide to getting (and keeping) a good, old-fashioned, husband-material kinda guy; and at a time when heartache had overwhelmed my still-developing feminist values, that sounded like the dream. 

(Plus, I’ve always been a bit of a 1950s enthusiast—I wear pin-up swimsuits, have an extensive apron collection, and paint on a red pout every single morning—so the book’s tagline, “Time-tested secrets for capturing the heart of Mr. Right,” came off as kitschy rather than archaic.)

The aforementioned breakup had ended with me in hysterics on the kitchen floor, begging my boyfriend to stay; and in that moment, I was fully (and frighteningly) aware that I had no control: not over my heart, not over my mind, not even over my body.

The neat, orderly setup of The Rules promised to restore total control with the application of just a few simple guidelines. All The Rules became my Bible.


Included in the Rules were commandments, such as:

1.      Don’t talk to a man first.

2.      Don’t call him (and rarely return his calls).

3.      Don’t “go dutch” on a date.

4.      Don’t accept a Saturday night date after Wednesday.

5.      Let him take the lead.

6.      Don’t open up too fast.

7.      No more than casual kissing on a first date.

8.      Love only those who love you.

9.      Don’t tell him what to do.

10.   Don’t go out with him more than once or twice a week.


The general gist translated to, “If you don’t put in the effort, you can’t get hurt.”  I couldn’t be upset that he didn’t call back if I never called him in the first place. I wouldn’t feel rejected by an unreciprocated kiss if I never made the first move.

According to the authors, Ellen Fein and Sherrie Schneider, men need to chase; and a woman who makes the first move denies them the thrill of the hunt.  So, while a man could, hypothetically, fall in love with a woman who takes the lead, he won’t value her as someone he had to work for and earn. Logical, no?

These rules worked beautifully. I became a master dater, enthralling men with my detached charm and infrequent availability (will they ever learn to ask for a Saturday night date before Wednesday?), and living a life free of why-isn’t-he-texting-me-back stress. I never knew dating could be so much fun!

When I started seeing Hugh—a guy that I really liked—I painstakingly followed all of the Rules to ensure our relationship would flourish. 


It did.

We fell in love. 


But a Rules girl doesn’t stop following the Rules once she’s in a relationship— she follows the Rules for life! Throughout our 3.5-year relationship, I rarely (if ever) initiated a text conversation, planned a date night, or even told Hugh I loved him unless he said it first.

I really, truly believe that following the Rules throughout the relationship lessened the pain of our breakup.


So, here I am: now, a 25-year-old single girl, and a bona fide expert on Rules-approved dating.  But, as I’m discovering, I know virtually nothing about that no-holds-barred, need-to-see-you-everyday, I-don’t-care-if-it-doesn’t-make-sense kind of dating that YA fiction and teenage dreams are made of.

The Rules have absolutely kept me from pain in my romantic endeavors…but have they cut me off from pure, unadulterated joy and love in the process?  In a word, yes. 

In the name of feeling all of the feelings, I broke the Rules for the first time in 6 years after a successful first date with John, a (semi) socially awkward writer with a self-deprecating sense of humor that I found adorably attractive. When a week went by and I hadn’t heard from him, I decided to take matters into my own [trembling] hands:


I was going to break the #1 Rule and make the first move.


The Rules had conditioned me to fear rejection so much that just the thought of hitting “Send” on an unprecedented text made my stomach drop and my palms sweat. I took a ridiculous amount of time planning out the perfect, brief, and oh-so-casual exchange in the “Notes” section of my iPhone (to minimize the risk of prematurely hitting “Send”, of course), where it sat for 24 hours before I had the nerve to copy-and-paste to John,

“Hey! I got the impression that dancing isn’t really your thing, but it’s Emo Night at the Short Stop on Tuesday which is always a good time. Let me know if you want to join!”

I pushed “Send” and watched as “Delivered” appeared beneath the little blue dialogue box. I did it! I texted a boy!  I was proud of myself, and terrified, and wanted to dance with excitement and throw up at the same time.

I had prepared myself for rejection, but what I wasn’t prepared for... was nothing. My phone didn’t buzz with John’s reply that night, and there wasn’t a text waiting for me in the morning. I checked my phone about 50 times at work the next day, and made my Mom text me just to make sure my phone was working. 

(It was.)

After 2 days, I deleted our text log: every time I saw “John” appear on the screen in my Messages folder, it stung.  

After 3 days, I started crafting a follow-up text just to check in.

After 4 days, I deleted his number to remove the temptation to text him a second time and compound my embarrassment.

After 5 days, acceptance settled in and I knew that John was actually never going to text me back.

The worst thing that could have happened happened.  And I was OK.  I am OK.


Texting John—maybe a small and insignificant move for some—taught me that I am worthy of asking for what I want, and I am strong enough to handle not getting it. As it turns out, the Rules have never given me control over my life. The Rules put all the control into the hands of the men I dated, and made me a spectator of my own life. The Rules filled me with an unfounded fear of rejection, and the Rules limited the love in my life. 


The Rules were made to be broken. 

Jessica DeFino is a wardrobe stylist and content creator in Los Angeles, CA.  Her work has appeared in magazines such as Harper’s Bazaar, Marie Claire, Conde Nast Traveler, L’OFFICIEL,  ELLE, and many more.  Currently, Jessica is focusing her attention on her organization I Dress For Me, a collective of strong women with style advocating for awareness, education, and prevention of sexual assault and sexual harassment.  You can find out more about Jessica and her cause here and here