Dating Myself Again
I canceled on myself after planning my first solo date.
Saw the event marked on my calendar and added little doodle hearts to make it special. Then, as the day neared, panic trickled in. What if people looked at me funny? What if it felt awkward sitting at a table alone? Would people be able to tell I was nervous? The irony is that I never had those thoughts when someone else sat across the table from me. But now that the reservation was for one, I was shaking in my boots.
Why did the thought of spending time with myself make me so uncomfortable?
I liked myself, right? It was the reason I’d decided to go on these solo dates. But like any distraction, this alone time left room for vulnerability to creep in. If the food was bad, you blame the chef. If the conversation was lacking, you blame your date. Horrible service? Tip the waiter, then leave a bad review (because in this economy, you should be tipping your waiters).
Many of us know how to be productive on our own. Few of us know how to enjoy ourselves alone. I know I didn’t. I’d perfected the art of operating around others: family members, friends, colleagues. But I rarely centered myself, creating intentional experiences solely to bring me joy. And I think many of us live this same way. We wait for someone else to create the experience we secretly desire, whether it be dinner, flowers, or other adventures, hoping it’ll make us feel special, all the while postponing our joy until the other person arrives.
The problem is that it places our happiness into the hands of another. Happiness is far too precious for that. And why dating yourself becomes even more important.
A few weeks ago, I shared a portion of bell hooks All About Love that stuck with me. The importance of self-love. Usually, we focus on mindset–positive affirmations, confidence, and self-esteem. While those things matter, they should also be reflected in the choices we make (see what I did there, lol). The habits we choose. The boundaries we create. The environment we build. Dating yourself is one of the most practical ways to bring yourself joy, because it allows you to discover who you are at your core. Each date adds micro-chains of information–what excites you, bores you, energizes you–bringing more alignment to your being, without assumptions of what should be.
At the moment, I can’t tell you if I have a guaranteed plan for doing this without the cringe factor attached. But what I can offer is a helpful guide to get you started. A guide I’m incorporating into my own journey as well. If you’re feeling intimidated like me, let's start small.
How to Start Dating Yourself
Stop Waiting - You don’t need a partner or permission. Choose one thing and show up.
Expect Discomfort - You’re going to feel like an awkward duck. That doesn’t mean you’re doing it wrong. It’s just new and part of the process.
Stay Curious - It can be easy for judgment to creep in. Ignore. Stay in the moment. Perhaps journal about it later by asking yourself these questions:
Does this feel natural?
What did I learn about myself?
Could I see this happening in my everyday life?
How did this impact my standards moving forward?
Repeat - One solo date won’t change your life. This relationship with yourself grows over time, like any other relationship. My rule of thumb is three. Three awkward moments until it becomes comfortable and worn in like new shoes (yes, I’m on a shoe kick right now).
Solo Date Ideas for Beginners
Need to Slow Down?
Coffee Shop + Favorite Book
Matcha + Journaling Session
Farmers Market Stroll
Solo Brunch
Fresh flowers
Need to De-stimulate?
Sunset Picnic
Outdoor Yoga
Nature Trail Walk
Get Some Sun
Visit a Botanical Garden
Need to Be Curious?
Library Date
Indie Bookstore Crawl
Museum Day
Attend a Lecture/Author Event
Research Special Interest
Need to Feed Your Spirit?
Take a Pilates Class
Get a Massage/Facial
Attend a Wellness Workshop
Sound Bath in the Park
Meditate
Need to Create?
Pottery/Painting Class
Vision Board Session
Thrift Store Treasure Hunt
Flower Arranging Class
Junk Journal Session
Need to Treat Yourself?
Solo Dinner Reservation
Dress Up and Visit a Lounge
Hotel Staycation
Go on a Mini Shopping Spree
The Real Takeaway
The greatest joy in dating yourself is realizing that your happiness need not be postponed. Your life does not begin when someone chooses you. It’s happening now. Today. The more you learn to enjoy your own company, the less likely you are to compromise yourself for the sake of companionship. You learn what peace feels like to you and protect it. That doesn’t mean you’ll never desire a partner or need anyone again. The goal is to learn yourself so completely that you’ll never abandon yourself. This is the only life you are given.
You might as well make it beautiful.
With love,
Alexandrea LeChelle 💖🫒
Founder & Editor-In-Chief
Sweet Freckled Olives
