Dating Yourself

In the quiet aftermath of heartbreak, a week of self-dates becomes a tender ritual of reinvention—marked by outfit shifts, solo rituals, and small indulgences that signal a slow return to self.

Ashley Olsen photographed carrying pink lilies in New York City. Photo by Splash News, via Vogue © All rights belong to their respective owners. No copyright infringement intended.

I sat in an uber, eyes welling, as the driver waited for me to click my seatbelt into its buckle. She asked what was wrong, to which I answered, shortly, “breakup”. She seemed to understand instantly, replying with one sentence followed by ten minutes of silence: “When you break up you grow up”. I knew exactly what she meant. 

In the following days, I decided to grow up. I spent the greater part of the week dating myself, committed to taking full advantage of the greatest opportunity for self-care, self-love, and new habits. Here is what the first three days post breakup looked like: 

Reinvention 

On the first day, I dedicated my time to reinventing myself. What does that look like? Concisely, it's buying a new wardrobe and new makeup that align with fashion trends I’ve been nervous to try. 

Starting off with reinvention gives you a fresh perspective on self-expression and how you choose to show yourself to the world. It also positively correlates with confidence, which is something that any newly single individual can stand to benefit from. I began by walking to my favorite vintage store in Montreal, and picking a few colorful pieces that stood out to me. I decided that, in this new era of life, I’d like to be unapologetically vibrant, both in outfits and energy. 

I purchased a red mini-dress, draped and cinched perfectly for summer, as well as a pair of micro denim shorts. I sought to veer towards the things I typically avoid in fashion: form fitting and revealing clothes. Leaning into discomfort was cathartic. 

Following the vintage shopping, I went to a beauty store to pick up two of my favorite products that had recently run out: a Dior foundation stick, and a Charlotte Tilbury lipstick in the shade of pillow talk. 

Getting dressed and feeling put together is the number one motivation to leave the house, and with these purchases, I felt ready to tackle the coming days. 

Relaxation 

I devoted the second day to going easy on myself, and placed priority on relaxation and self-care. I began the day with a trip to the nail salon, where I chose the most vibrant cerulean blue to adorn my nails. Again, this was in hopes of feeding into the newly sought vibrancy I was going

after. I ended up getting a massage at the salon as well. We carry tension in our necks, shoulders and back that often go unrecognized until excruciating pain is involved. I find that my mental grievances worked their way to my back, so this massage was much needed to invoke relaxation. 

When I got back home, I decided to put on my new outfit and a soft makeup look. I felt unstoppable, the power of looking good and feeling good ringing true. I decided to buy myself flowers. I gathered enough roses for a bouquet and wondered why I’d never granted myself this gesture before. There is something unreplicable about the love you give yourself. 

To end the non exhaustive day, I took myself out for a beer, alone. I ended up watching the people around me, and forming narratives about what could be happening in their lives. I felt powerful and confident, being alone at the bar without needing to explain myself to anyone. 

Reflection 

I spent the third day reflecting, now that the heartache had relatively subsided. This entailed hours of journaling in a cafe, as well as a trip to the bookstore, and an evening of reading. 

Through journaling, I was able to deliberate on answers that I may not have gotten otherwise. The truest closure is the one you can grant to yourself. Journaling is a way into your mind’s eye, and I plan to do it daily. 

I finished up my entry and quickly headed over to the second hand bookstore that I frequent. A combination of preloved books and my preceding hours of reflection led me to choose Madonna In a Fur Coat as my next read. 

As I sat in my apartment upon return, I nuzzled myself into the couch and read all two-hundred pages of the book, cover to cover. It was a liberating feeling to read another love story without a happy ending. They’re realistic in ways that are tied up, pleasant endings are not. 

So, yes, it is true. When you break up, you do grow up. You’re forced to confront discomfort, risk-taking, and change, and it’s all for the better.