How To Date Yourself

Friendship is an extremely important part of life, and not one that should be taken for granted. Over the past few months, I’ve had the pleasure of spending real quality time with many of my friends, who I’m extremely grateful to have in my life. Recently, though, it occurred to me that I haven’t been spending nearly as much time by myself as I used to.

My whole life I had been pretty bad at knowing what to do when left to my own devices. It’s no secret that I’m a “people person”, and it just had always seemed easier to find things to do when I was with people I cared about. A couple years ago, I started making a conscious effort to spend time by myself, and it’s no coincidence that this happened around the time that I discovered my love for guerrilla art. Hanging out with myself has turned into not only a comfortable experience, but an enjoyable one. In fact, sometimes I prefer it.

Taking myself out on the town started to become an adventure of its own. What typically social activities could I dare myself to engage in alone? Through this process, I realized how important it is to date yourself. If you’re unsure how to do this, I’ve got some advice.

1) Assess your current comfort level.

Think about going to the movies alone. How does that make you feel? Do you cringe at the idea of people seeing you enter a theater alone? Does the idea of getting your own tub of popcorn that you won’t have anyone to share with frighten you? Or perhaps getting your own tub of popcorn sounds ideal because you can put as much butter and salt on it as you want, and it can permanently rest on your lap (or the seat next to you) instead of getting passed back and forth.

Use the feelings you get just imagining these activities to gauge where a good place to start would be. The concept of dating yourself is likely out of your comfort zone, but we don’t want to throw you into the deep end without those floaty arm things.

2) Designate a time to do it.

This is especially important for your first time. Schedule this time with yourself the same way you would with a friend. Put it on your calendar, and mark yourself as unavailable. If you keep allowing other engagements to take precedent, you might never get started. So write it down and follow through.

Once you start, figure out what a good schedule would be for you. Do you need to designate self love time once a week? A month? This is all based on how you feel and what your schedule will allow. You obviously have other commitments that you need to take care of, too. But if you decide that every month you’re going to take yourself out, then do it.

3) Have an activity idea, but be extremely open to spontaneity.

If you have no idea where to start with date ideas for yourself, here are some options: see a movie at the theater, eat dinner at a restaurant, walk around with a camera, visit a museum, go shopping for a new outfit, have a spa day (manicure, massage, etc.), create a ritual, take a day trip to somewhere like the beach, do some yoga outdoors, take a drive to nowhere in particular, drink at a bar, have an art picnic, take a class, be a tourist in your own city. The activities can be as introverted or extroverted as you’d like. You want to do things that interest you. If that’s reading on a blanket in your backyard, then go read on a blanket in your backyard!

So pick something out to do, but don’t plan too much more than that. One of the best things about being alone is that you don’t need to cater to anyone else’s needs. There are no compromises that need to be made. Order what you want, wear what you want, do what you want. So make sure you’re open to all options! Engage in your environment. Act on impulses. Check out nerdy stores that your friends wouldn’t enjoy, strike up conversations with interesting strangers, and say yes to new things. Pay attention to your senses, and your body in general. Are you thirsty? Do you have an overwhelming desire to wear your sunglasses indoors? Do you really really really just want to stop walking in your tracks and shake your butt like you’re Beyoncé? Go ahead. The only one who can judge you is you.

4) Turn your phone off.

Yeah, for real. Or at least on airplane mode. Have it with you, obviously. You’re alone and it’s even more important in case of an emergency; but don’t use it. At this point in life, our phone is a giant connection to others. We have social media, texting, and more at our fingertips, but this time is about you. Think about how rude it would be to surf the web while you were on a first date with a someone else. Don’t be rude to yourself. Allow yourself to be totally alone, without the temptation to tell your friends and followers every move you’re making. It’s okay to feel disconnected and lonely, I promise.

5) Reflect and learn.

Take some time to think about the date you had with yourself, whether it’s an internal monologue, a blog post, or a conversation with a friend. Figure out what you found exhilarating or enjoyable. Are there things that you were surprised you were able to do alone? Do you feel like you can push yourself further next time? (Maybe instead of eating alone at Panera, you go to a sit down restaurant and say the words “Table for one”.) Or was it just way too scary and you want to try something completely different next time? Based on your experiences, you can alter future outings to be the best time you’ve ever had by yourself.


Ultimately, just allow yourself to be a little open and vulnerable to this concept. Over time, it won’t be a big deal anymore (if it ever was). You’ll be able to embark on an activity solo with no hesitation the same way you would about doing a chore or errand. You’re always around you. There’s no getting away! So make the time you spend, the way you live, fun.

What are some dates you’ve taken yourself on?