Why Throwing Away My Dating Rules Was The Best Decision I’ve Ever Made


I’m a logical, left-brained kind of woman. I have spent my life weighing risks before making decisions; figuring out formulas for success. I find comfort in knowing 1+1=2, always. I, by nature, don’t like surprises. A sure bet will always be my choice over a more seductive roll of the dice. 

I used to approach love and relationships very much the same way. I had a plan, a system, and rules to follow. I looked at match.com profiles with the same discriminating eye I would review a resume from a potential candidate for a job.  I wouldn’t go on a first date on a weekend, I wouldn’t sleep with someone on the first one, two, or even third date. I had specific date outfits, carefully crafted to be a perfect balance of sophisticated and sexy, but not slutty. I had witty stories, charming retorts, and thoughtful questions. I looked at dating as a numbers game. I thought if I went on enough dates, the odds would be I would I find someone, THE one. It was a solid, well thought out plan, in theory.

Do you know what happened? I failed. Miserably. I went on so many dates and had dozens of texts messages from nameless numbers. I calculated my responses, my response times.  I felt like a robot. I wore the same outfits, told the same stories. I went to the same restaurants week after week, month after month. It felt like a job, one I couldn’t wait to quit. 

What I learned was you can’t formulate a relationship.  1 + 1 doesn’t always equal 2 in dating. People don’t fit in a nice little box you can wrap a bow on. Relationships aren’t black and white; much to my disappointment.  There are thousands of articles in magazines and countless books written to tell us women how to “catch and keep a man”.  Many people have made a fortune on preying on our logical minds and vulnerable hearts. 

I tend to believe we will face a challenge over and over again until we learn the lesson we’re meant to learn. My lesson here was to live in the gray; to get messy, and let go of my rules and my calculated plan. I learned to date as myself, the person they would be getting in a month, or two, when my Polly perfect routine was too exhausting to keep up with.

Now, I don’t look at my dates as a pro/con list.  I don’t weigh education, jobs, and child status as heavily. In fact, I like the ones who have lived, who have taken risks, who have lost, who dared to jump feet first. I still don’t know after how many dates it’s appropriate to sleep with someone.  I’ll do it when it feels like the right time. It might be the second date or the fifteenth. I feel anyone who will judge me for that isn’t someone I should spend time with. Anyone hanging around just long enough for me to sleep with them is missing out, because I have a hell of a lot more to offer than sex.

I’m sure you’ve all heard the quote, “don’t date anyone you wouldn’t marry”, and I used to base all my dating decisions around this theory. How closed-minded of me. I have had some amazing experiences and relationships that were not black and white. Some of them were for an evening, or a weekend, or maybe a few months. I’ve been more vulnerable with some of these men than I have ever been with some of the men I’ve had long term relationships with. Time doesn’t equal significance.

Not every relationship goal should be marriage. Sometimes it’s the freedom and lack of structure with someone that facilitates growth; pushes you to question your beliefs, and how you see yourself amidst the culture and societal norms we face day in and day out. I’d take that over a joint bank account and bickering over unloading a dishwasher any day. Although, it would be nice to have someone else pitch in with the dishes. 

I’ve learned to date with recklessness, and it was exactly what this type-A Virgo needed.  To swing the pendulum the other way and take some pressure off of me, and the men around me. I’ve learned to live in the moment and not stress about the future. I set out to find a husband, but what I really found was myself, and some beautiful humans along the way.Thought Catalog Logo Mark

A girl in her early 30’s navigating dating, career, and friends.

Keep up with Piper on chasingpeter.com

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