Why Every Single Woman Should Date Herself

How a Breakup with Booze & Boys Helped Me To Truly Love Myself…And Why I Think it Could Help You Too.


I walked into the dimly-lit theater and apprehensively took my seat. At 31, this was the first time I’d ever treated myself to a movie solo. My thirty-first year would be full of many firsts. This was my first of many dates with myself.

The catalyst behind this newfound relationship with little old me was born out of necessity. It was only a few months before that I’d made the decision to take a break from alcohol. A “party girl” in my 20s, I’d had a sudden sense that my life might be better without it. So, as terrified as I was to navigate the world without a substance that had given me the confidence to date in the first place, I listened to my intuition and broke up with booze.

Before I go too far, let me spell out what life looked like for me at this point, because it looked pretty “normal” for a woman my age. I was a young, single, successful woman living in a vibrant city. I had an active social life - which meant tons of happy hours and weekends spent boozing out on the singles scene. I was meeting men on dating apps and at bars; neither of which were leading to productive relationships. I clung to relationships that weren’t entirely fulfilling and went on lackluster dates all because I believed the lie that I was on some sort of time clock now that I’d passed 30. I thought I had my life together; it was beyond me why I wasn’t finding contentment in it all.

Everyone assured me the life I was living was so fun, fancy-free, and fabulous. In reality, I felt anxious, stuck, incomplete, and emotionally exhausted. I was sure there was something better out there, yet I continued to choose the monotonous hamster wheel of the singles scene because it was “normal”. I share this because maybe you find yourself in a similar place: doing all of the things that society tells you are “right”, but feeling like there’s something incredibly important missing. I didn’t know why, but I sensed that ditching booze was an important first step in finding this missing piece…I was right.

Little did I know that eliminating alcohol from my life would fuel one of the most intense and important periods of personal growth I’m sure I will experience in my lifetime. Without the distraction and numbing-effects of booze, I was forced to spend time getting intimate with thoughts, feelings and wounds I didn’t even know existed. Once the veil of alcohol was lifted, I had no choice but to stare my insecurities and limiting beliefs right in the eye. The fact of the matter was, life wasn’t automatically unicorns and rainbows just because I’d quit drinking. I realized quickly that I had work to do...and a lot of it.

This meant resisting my temptation to throw myself back out on the dating scene, even though - at the time - I desperately wanted the comfort of a romantic partner. Instead, I learned to find comfort in my discomfort. I learned to sit with my feelings instead of distracting myself with overloading my social calendar, or mindless swiping and chatting with internet strangers, or even binging on the latest Netflix series. No, instead, I took valuable time to work on the most important relationship in my life: my relationship with me.

So, I deleted all of those pesky dating apps and made a pact with myself that I wouldn’t download them again until I felt ready (note, “readiness” does not equate to boredom or loneliness or the need for validation or attention). Truth be told, I had no idea what “ready” was, but I trusted I’d recognize it when I got there.

As I entered into the strange new land of dating myself, I made a concerted effort to set aside time I would have perceivably spent getting to know a romantic partner, simply getting to know myself. It looked like sitting at home and reading or journaling when it would have been easier to scroll through my feeds or mindlessly binge an entire season of some crime drama (don’t worry, I did a little of that too). It meant getting comfortable with taking myself on movie dates and treating myself to a solo breakfast or coffee shop date and letting myself be guided into conversations with complete strangers also seated solo at the cafe counter. It looked like going on long walks with only an audiobook as my companion. Truly, dating myself looked a lot like what it would be like dating a new romantic partner, I was just on my own for this one. Now, you’re either thinking this sounds entirely wonderful or incredibly depressing and dreadful. In all honesty, it was a bit of both. Spending this time with myself took discipline and curiosity. Before there was comfort and peace, there was loneliness and doubt. It was a tedious (still ongoing) process of retraining my brain to sit with my thoughts and feelings rather than distract myself.

Through this process, I came to know, love, and respect myself more fully. As time passed, I was overcome with a sense of strength and power that came from knowing I - a thirty-something woman - was choosing to embark on a journey of growth and self-love most women wouldn’t begin to make until mid-life...and that some would hardly choose to make at all. Day-by-day, I felt a sense of empowerment and resilience in knowing I could do normal things and hard things without the need to treat myself to a drink or quiet my nerves with a bit of liquid courage.

Slowly, I started to realize that I was seeing life through the eyes of someone who had found love, compassion, empathy, and appreciation for herself. Through all of the work and skipped social plans and dates with myself, I realized I’d miraculous come to love myself quite deeply. Of all of the relationships I’ve had, and of all I will have in the future, I will attest that this is most important and the one that I am most proud of.

The journey of dating myself is far from over. Personal growth and self-love are part of a practice that will always require attention and work (just like any relationship). Through this season, I’ve found what “ready” truly feels like. It’s certainly nothing like the sense of longing and need for companionship I felt before. No, “ready” feels much more like a subtle calm. It’s a sense of being at peace in the present and needing nothing more. It’s a sense of knowing that I have all that I need and seek for no completion outside of myself.

I truly believe that my breakup from booze and boys was one of the most important things I share frequently about this experience because I know it is a non-conventional choice that could seem scary for a single, 30-something (especially for that girl who believes she’s on a time clock when it comes to dating, marriage, etc). Let me assure you, time will seem to expand when you make the choice to love yourself first. Personally, this time has made me feel more light and carefree. I feel full of love, joy, and energy that I want to share in all of my relationships; romantic or not. I know this newfound love for myself will inevitably cause me to vibrate at a higher frequency, attracting more suitable matches (and opportunities of all sorts, I suppose) into my life. I can’t wait to see what the next let of this journey entails. Stay tuned.

For my single ladies who have done the work and STILL feel like they’re not getting this dating thing right, I’ve got something for you. Click here to learn more about my new Mindful Dating Masterclass and to join the waitlist (enrollment opens soon).