How to Date Yourself in 10 Ways

Another Valentine’s Day has come and gone, and I’m left thinking about Cupid’s arrow and L-O-V-E.

This year, though, it was less about me spending an hour shaving and more about reflection, introspection, and a journey into the heart of self-love.

Believe me, I’m no expert at the fine art of fierce self-love. I’m generally much better at self-deprecation and self-sabotage.

Backstory: I first began processing the idea of dating myself as I was going through a major, major breakup last year. It was the most defining relationship I’d ever been a part of; it was with a man who was the first person to ever know me- the good, the bad, and the early in the morning me (yikes). It was a tumultuous, terrible, wonderful, bright, miserable, enlightening, and invigorating relationship- all at once. But, he just changed his mind one day. Something about not being able to stand me or something. And when it was over, I was, simply, alone.

I didn’t know where to turn for the highs and lows I’d become so accustomed to over the years. I didn’t know who to run to or how to distract myself from reality. I didn’t have a definition anymore. It sucked big time.

I was in hell. And not because I missed him. I was in hell because I knew in my deepest deep that I was just going to have to be me. I didn’t know me and I didn’t really want to get to know me, either. It seemed too scary. What if I didn’t like me once I got to know me?

Without much of a choice, and in a last ditch effort to pull myself up from the pile of potato chip bags and Ray Lamontagne CD’s, I took myself on a date. I went to see a movie. Alone. By myself. Yes. Me in the theatre. A movie I couldn’t talk anyone else into seeing with me. So I went. Just for me. And I dressed up. And I bought myself some sour candies and a big old popcorn. And it. felt. so. good.

It actually was really scary. It was invigorating. It was wonderful and terrible and enlightening and gave me all the things that my relationship used to give me. And, like the “duh” billy club beat me over the head, I deeply understood that the most important relationship that I will ever have, the truly defining relationship that I can count on forever, is the one with myself. I think Carrie Bradshaw said that once. Which makes it true.

I began thinking: I had devoted too much time to worrying about the opposite sex, busying myself with finding “the one” to fulfill me.

Then, somewhere a shrill voice inside me said, “WAKE UP LADY! You’re “the one!”

And I also realized, that like any relationship, my relationship with myself would take cultivating and attention. Work and Effort. Thought and Care. It would take putting myself in uncomfortable situations and pushing myself to make me a priority.

Stay with me, here. Give this idea a moment to sink in. I asked myself some hard questions.

What if I just met me? Would I make a good impression on myself?

Would I have a crush on me?


I’ve got to give it attention, this real-life romance with myself, as if it’s a brand new relationship.

I don’t know about you, but washing my hair is a must for a first date. Also, clean underwear. I psych myself up, I talk kindly about myself, and I don’t talk about my past relationships (or gas).

For me, it looks like putting my best foot forward, as if each day is a first date with myself. And it goes a little something like this…

How To Date Yourself in 10 Ways:

1. Get ready: shower, shave, put on your feel-good make-up and do your hair in a fun, flirty, very you way. Every day. Make time for it. Maybe even get your nails done, and a fresh new haircut. Whatever it takes to make this feel real.

2. Wear something fun that makes you feel oh-so-good. Show off your personality. Think about the you that you want to present to the world. You can forget a cleavage-bearing shirt everyday, unless that’s your thing.

3. Clean your space. Imagine you’re expecting a guest to pick you up for your date. You wouldn’t have an unmade, sick-dirty bed if you were going on a date, would you? No. You’d pick up the trash off of the floor and put your laundry away. You’d also probably do your dishes and clean your toilet. Probably.

4. Tell your friends how excited you are. Only this time, it’s how excited you are to get to know you. Tell them your goals, your specific hopes, everything about you that makes you giddy. And when they follow-up to see how your new relationship is going? Be honest. Use your friends and support system to hold you accountable.

5. Have a plan. Lunch? Movie? That new restaurant or museum? Walk in the park followed by wine in the grass? A home-cooked new recipe prepared at home? Do it. Give yourself the courtesy of scheduling and keeping a date.

6. Give yourself a thoughtful gift. Flowers. Candy. A mix tape of your favorite tunes. Those earrings you’ve been eyeing. And celebrate milestones. Days, weeks, or months of progress deserve attention, just like in any relationship.

7. Leave yourself love notes. Sticky-notes on the mirror, your favorite quote scribbled inside your notebook, an inspirational photo, or

8. Talk only positively about yourself. You wouldn’t go on and on about your nasty habits or your dysfunctional family or your bout with depression on a date, would you? Maybe you would, after some wine, but focusing on the positive, at least this early in the game, always yields better results.

9. Get to know you. Journal it. Learn who you are, what your goals and dreams are, and who you want to be. Your best self. Explore what that looks like. Map it out. Devote time to this part of the relationship; it will be the foundation that keeps you in a happy place when the going gets tough.

10. Kiss yourself goodnight. Develop a night-time routine that is all about self-love. Maybe a cup of tea. Maybe a soothing read? Maybe some music? Sink into bed with that feeling that it’s all falling into place.

It’s seems so very simple; clean underwear and sticky-notes on mirrors, yeah? It’s more than that, but it’s just that straightforward for me. It will take days and days of sticky notes and clean underwear and kissing myself goodnight, it will take the practice and dedication that I’d usually be putting into my relationship with someone else, it will make me uncomfortable sometimes, and it will make life feel magical because I’m learning that I can give myself everything I need.

One of these days, the love of my life will unexpectedly appear and it will be me, looking back at myself in the mirror.

[photo credit: weheartit]


Real Talk
In real time

Inner truth + outer alignment = unapologetic joy

Get my weekly-ish love notes to help you reclaim an intimate, honest + joyful relationship with yourself, for the good of all.

Real Talk
In real time

Inner truth + outer alignment = unapologetic joy

Get my weekly-ish love notes to help you reclaim an intimate, honest + joyful relationship with yourself, for the good of all.