I Took Myself on Dates for a Month To Find Joy Outside My Relationship

Photo: Getty Images/Phan Minh Cuong An EyeEm
You know who should be your most important Valentine? Yourself. With My Own Valentine, we’re sharing essays about self-love, products that facilitate self-love, and ideas for how to love yourself more—regardless of your relationship status.

Throughout the past month, I’ve gone on four dates, and none of them involved my boyfriend. They were solo dates for me to simply spend time with myself. I went to a museum to wander through a motion picture exhibit; I saw a movie in a theater; I took a 50-minute train ride to Central Park, where I found a park bench, sipped coffee, and people-watched. I didn’t do all of this alone because I don’t like my boyfriend or want to avoid spending time with him. But the truth is, we've been together for so many years, I figured committing to the concept of dating myself could function as a great check-in outside the scope of my romantic partnership.

Experts In This Article
  • Josh Klapow, PhD, clinical psychologist, performance coach, and the chief behavioral scientist for health-engagement technology company ChipRewards

Soon after getting together in college, my boyfriend and I fell into a clichéd relationship dynamic of functioning as a single person. We still share interests and social circles, and after a big move from our longtime home in the Philippines to New York City last year, we now also share an apartment, clothes, and a cat.

Without many family members or friends nearby, we’ve come to rely solely on each other for companionship, too, which leaves little to no alone time for ourselves, save for the weekday hours we dedicate to our respective jobs. We spend many weeknights at home, sitting side by side on the couch, making our way through Netflix’s catalog. On weekends, we make pasyal (“sightseeing” in Tagalog), meandering through our neighborhood by foot, or hunker down in a coffee shops to read our own books, but in each other’s company.

Although I relish the comfortable rhythms of our relationship—perhaps more so now than ever before in this new and unfamiliar city—I’ve realized that much of my joy was tethered to it. I love my boyfriend, but I realized I didn’t know how to be alone in my own company anymore. And it was time for me to re-learn the skill.

The value in learning to be alone, for folks in any relationship status

There is merit in learning how to be happy in your own company, regardless of your relationship status. “One of the core elements that leads to fulfillment in life is comfort and contentment with ourselves and by ourselves,” says clinical psychologist Josh Klapow, PhD. “If we don’t feel safe and secure with ourselves and by ourselves, then we are perpetually in a state of looking for security outside of ourselves, or we are in a state of not feeling secure.”

"One of the core elements that leads to fulfillment in life is comfort and contentment with ourselves and by ourselves.” —Josh Klapow, PhD, clinical psychologist

Being happy or just content with being alone can benefit all relationships—be them romantic, platonic, or familial. A small 2018 study of adults older than 65 published in The Gerontologist concluded that time alone helped participants regulate emotions, and, thus, better prepared them to interact with others. Though conducted on a specific age group, it makes sense that the results could apply to all people, reflecting the adage that says to fill your own cup first and only feed others with the overflow.

However, many people fear solitude, and largely because they conflate being alone with loneliness, the latter of which carries a negative connotation. Unlike loneliness, though, time spent alone can be enjoyable, should one choose it. And taking yourself on a date is one way to learn to be—and enjoy being—your own company.

The case for taking yourself on dates

Solo or self-dates are exactly what they sound like: Intentional time with just yourself during which you are both the wooer and the woo-ee. You decide how your ideal date looks—where you’ll go, what you’ll do, and for how long. Initially, the idea of taking myself on such dates didn’t appeal to me, but that changed after reading Julia Cameron’s The Artist’s Way. The best-selling self-help book aims to help readers tap into their inner creativity, and it led me to reimagine the vast possibilities of a self-date and the value going on one might offer.

In the book, Cameron recommends going on artist dates, or a “once-weekly, festive, solo expedition to explore something that interests you.” While the primary purpose of Cameron’s artist dates is to inspire creativity, I imagined that an excursion centered on something interesting to me could also qualify as an opportunity to reclaim time for myself and revisit—or discover—what makes me happy. I wasn’t off the mark:

“Cultivating our own interests is a wonderful way to either remind ourselves or learn what brings us joy and fulfillment,” says Dr. Klapow. He adds there is power in knowing what makes you, yourself smile, and by allowing yourself to pursue what brings you joy, you can find contentment, whether you have a partner(s) in the picture or not.

My takeaway on self dates after a month of them

When I took myself out on a date, I always dressed up. The ritual of doing so helped differentiate my solo dates from any other small moments of solitude I have. The occasions felt special, and with a reason to wear something other than pajamas, so did I. I was suddenly a woman with places to go and things to see.

When I took myself out on a date, I always dressed up. The occasions felt special, and with a reason to wear something other than pajamas, so did I.

My dates—with Cameron’s artist dates as inspiration—revolved around casual activities that weren’t artistically connected. I found myself drawn to public spaces with visual stimulation, like museums, movie theaters, and parks. With something on which to focus my attention, I was able to be present and avoid overthinking, which I tend to do whenever I have moments to myself. This was a welcome change to that typically buzzing internal monologue.

That’s me, though—your ideal date might look different. And according to Dr. Kaplow, the purpose here is to do something—anything—you enjoy by yourself. Solo dining doesn’t sound appealing to me, for example, but if that’s your idea of fun, by all means, wine and dine yourself.

After four self-dates, I wouldn’t say that I’ve unlocked any notable new level of self-contentment and security. But taking the time to be alone no longer feels like an afterthought. It became something I looked forward to. It helped me both decompress and allowed me to dedicate time to pursue my interests and remember that I’m not just one half of a couple.

I initially thought that it would take a moment to figure out or even just remember what my interests were outside my relationship. I was surprised to find that just by being with myself, I was able to remember things that I wanted to try but put off for so long, simply because I was waiting for someone to do it with me. With this in mind, taking myself on dates served as proof that I didn’t have to wait to try new things; I could do them when I wanted.

My boyfriend has taken up self-dates as well. We often send each other a message or two while we are apart, but mostly, there is a mutual respect for the alone time we’ve carved out for ourselves. It’s benefited our relationship; we have more stories to tell one another when we arrive home from our excursions. More importantly, though, I’ve learned from self-dates that I have more compassion and patience than I thought I had—and it feels good to give some of that to myself.

Our editors independently select these products. Making a purchase through our links may earn Well+Good a commission.

Loading More Posts...