What I Learned When I Started Taking Myself Out On Dates Every Week
“Alone?” the waiter asked in a Spanish accent, two menus in his hand. “Yes,” I said as I sat down at a table for two, couples occupying the tables around me. “Alone forever?” he asked, laughing. “I hope not,” I said, forcing myself to smile as he handed me a menu and walked away. Maybe this was a bad idea, taking myself out on a date, trying to go out alone for the first time — to a hip L.A. café on a Sunday morning, no less — since my boyfriend and I broke up.
Did that red-headed woman with the cool bangs, cherry red lipstick, and tattoos just look at me with pity, and point me out to her hot boyfriend? Should I pick up my phone and pretend to call someone who wasn’t coming to meet me? Should I start emailing someone? Should I get another menu and put it across from me as a prop, indicating that I’m only here alone temporarily… waiting? Or should I simply leave?
I stared at the empty seat across from me, my new brunch companion, a reminder of what I no longer had — as though it would be filled the more I looked at it, that my ex-boyfriend would magically appear when I blinked and say he changed his mind about us, that all his doubts had been resolved. My eyes started to water — I’d hate for the red-headed woman to see me cry — so I hid behind my menu, debating between flatbreads: mozzarella, spinach, potato, or beef? Too many choices.
When the waiter returned, I pointed to a flatbread with a Turkish name, trying to pronounce it syllable-by-syllable like I was back in kindergarten. The waiter said it takes practice, adding that he just learned English this year and now he's learning Turkish foods. “Your English is good,” I said. “I try,” he said. “Don’t worry. It’ll get easier.”
Truth be told, I used to hate the thought of going out alone — not to the grocery store or an ordinary activity like that, but going to do something that I’d only done with an ex, like going out a cafe in L.A.. And, the thing is, the more I got out of my comfort zone and started taking myself out on dates every week, the more life-changing lessons I learned along the way. Not only did I go out solo, from brunch to dinner dates, but I also started doing activities that either my ex didn’t want to do (and I didn’t want to do alone at the time) or things that I’d never tried before.
One week, I’d go hike a new trail in mountains I hadn’t explored before; another, I’d go see Milky Chance in concert. These were opposite extremes — one was appreciating the quiet, solitude, nature, and no WiFi connection around me while the other was amidst an insanely loud yet energetic crowd, where it was also easy to get a lot of thinking done. The more that an event was one that people didn’t tend to do alone, the more I’d push myself to do it. In every scenario, I’d discover that the end result was worth the initial few minutes of awkwardness à la, "What the heck am I doing here?"
Yes, I had friends I could have contacted to go out to eat with or try a new hiking trail, but there’s something about doing things on your own that builds your self-esteem and reassurance like nothing else can. Even if you have a significant other, it’s still healthy to spend time with yourself. All that said, I learned several life-changing lessons from taking myself out on dates every week.
1. Self-Confidence Came Easier
I happened to be waiting in line for the bathroom at the same time as the red-headed woman and it turned out that all of her pity stares were really not — instead, she said she admired that I could come eat at a popular brunch spot alone, especially when it was so crowded. “I’d never have the confidence to do that,” she said. I was shocked; to me, she looked like the epitome of self-confidence. However, her saying that motivated me to go on more dates with myself after that first one.
And, ever since that initial date alone, when I’d first pulled out a bunch of props to make me look less alone, I no longer let myself use my phone or other props on future dates. Instead, I’d make myself sit still in any awkwardness until it faded, and then focus on other things — from people-watching to taking notes in my journal (pen-and-paper style, no phone allowed). Date-to-date, my solo dates got easier, just like when you date somebody else — the first few dates may have awkward moments, but they get easier over time.
2. I Learned The Value Of Meditation
Before I started dating myself, I was *not* into meditation at all. Friends and exes had encouraged me to try it, but I always had an excuse not to get into it; after a few minutes of sitting in silence with them, thinking of a million and one other things I could be doing instead, I was done. However, when you start going out more alone, some of those things are silent: hiking, biking, kayaking, you name it. You have no choice but to reflect and meditate, and you learn to appreciate the silences, being disconnected from your phone, and thinking about what truly makes you happy in life.
3. I Learned The Importance Of Pushing Myself Outside My Comfort Zone
The more I started doing things alone — like sunset kayaking without my ex sharing a kayak with me — the more I become self-assured, especially when I’d do things out of my comfort zone, like kayaking on the open ocean (which is a lot different than kayaking on a lake whose circumference you can see). So, not only would I do an activity I enjoyed, and use the kayaking time as a form of meditation and way to alleviate stress, but I’d also end up leaving feeling more comfortable in my new skill (i.e., ocean kayaking alone).
4. I Explored Interests I Didn’t Even Know I Had
I knew I’d already liked kayaking, but the challenge was mastering it alone, and also not just on a lake. So, when taking myself on dates, I brainstormed all the things I’d ever wanted to do, like exploring caves in Slovenia. Yes, that’s a pretty specific one, but once you think of all the things you’d like to do, you don’t have to wait for a friend or significant other to have time to go with you — you just learn to make it happen, because the payoff is much better than regretting not doing it.
5. I Learned How To Make Friends When I'm Alone
Remember the red-headed woman from above? Well, when we spoke at the restaurant, we ended up exchanging numbers and meeting for coffee the following week, and for weeks after that. The same thing happens during many of my dates with myself — even though I have alone time and appreciate it, making new friends comes with the territory, too. For instance, I’ve met new people everywhere from going to a movie in L.A. alone to going on an island tour in Croatia alone. During the latter, I befriended a couple on their honeymoon, and when we coincidentally ended up in the same Croatian city a few days later, we met up again... and again. So, you never know.
Plus, when you’re out alone, you’ll probably run into other people alone. On one of my solo dinner dates, a guy was also having a solo dinner date and we soon got to talking — and it turned out he’s a writer, too. Although we live thousands of miles apart, we morphed into becoming email pen-pals, and our e-friendship is as great as ever.
6. I Adapted A “Now Or Never” Attitude
You know how you want to try a new restaurant, go see a movie opening weekend, or take a trip to Europe? Well, when you date yourself, you can do all those things anytime you’d like — you’re on your own schedule and don’t have to wait until somebody else is available to go with you. By adapting a “now or never” attitude, sure, you can still do things with your friends or significant other, but if you want to make sure these things actually get done instead of being put off, perhaps infinitely, now’s the time to do them. Chances are, like me, you’ll love that you had the experience versus just wishing it to happen and not knowing when.
7. I Learned To Manage My Finances Better
When you date yourself, you and you alone are responsible for all the money you spend. So, it goes without saying that your relationship with money should be an important one. Of course, there are plenty of free dates to take yourself on, but you also learn to balance the free with the not-as-free. Some days, I’ll drive along the ocean, only spending money on gas and perhaps a sandwich. Other days, I’ll go see a band play or try some new place for dinner. In any case, taking myself on dates can be cost-effective, depending on what I want to do that day or night. And, just like when you’re in a relationship with someone, you can set money aside and save up for bigger experiences, like taking a trip.
8. I Learned To Be A Better Dater
Many relationship experts say that you can’t love someone else until you love yourself — and that you have to enjoy your own company before someone else can appreciate your company, too. In addition, it’s a good lesson in being happy with yourself, whether you’re dating somebody or not. Although I took several months off from dating after my last serious relationship — except for the dates with myself — when I started to go out on dates again, I realized that I was a better dater (at least, I hope so). For instance, I was more confident when a guy would ask me where I liked to go on dates (versus just saying, “I don’t know — you can decide”) and if the date didn’t go as well as planned, that was OK — I still had myself to hang out with.
9. I Became More Self-Sufficient
I thought I was independent and self-sufficient before I started dating myself, but the more places I took myself to, the more I realized I was more independent and self-sufficient than I thought. After all, if something went wrong, I had no one to turn to but myself. For example, after my grandmother/best friend died, I had to grieve and get away from big-city life and the sound of ambulance sirens that I’d heard way too often as her health declined in Chicago. Her death reminded me that life is short, so instead of returning to my life in L.A., I decided to do something I’d always wanted to do: live abroad.
So I became a digital nomad, working remotely in different locations. Doing so is an excellent lesson in dating yourself, as it’s a constant game of juggling: balancing remote jobs, constantly finding new housing, making friends, exploring new cities and towns, and dating yourself in different countries. If I get escorted off a Switzerland train for sitting in first class versus second, I only have myself to blame. If my phone dies from the zero-degree temperatures when I’m using Google Maps to find a hospital in Bulgaria when I’m sick, it’s my fault for not carrying my back-up phone charger. Basically, taking yourself on dates is the best way to practice independence and self-sufficiency.
All in all, even when you’re in a relationship, I think it’s important to date yourself and have alone time outside of your partner, friends, and family. You’ll get to know yourself better, which will make you a better partner, friend, and family member down the line. Like that waiter had said, “Don’t worry. It’ll get easier.” Turns out he was right, as it gets easier and easier as time goes on.