How To Take Yourself Out On A Date

Woman holding a glass of wine in a bathtub, facing the outdoors.

Self-care really boils down to one thing: looking after oneself. Taking actions to make sure that you’re healthy—physically, mentally and emotionally. And, what better way to to that than investing in a relationship with yourself?

When you strip away all the face masks and hashtagged Instagram posts, self-care really boils down to one thing: looking after oneself. Taking actions to make sure that you’re healthy—physically, mentally and emotionally.


For most of us, this means eating vegetables, striving for eight hours of sleep, squeezing in the odd spin class and downloading a meditation app. Those are all productive and powerful methods of looking after ourselves but sometimes they can feel more like work than care. 


Enter another way of practicing self-care: dating oneself.


What it means to date yourself

Dating yourself is all about investing in your relationship with yourself. It means spending quality time with yourself, doing something other than errands, or making dinner, or going to the gym, in effort to feed your own passions and boost the love and care you direct inwards. It’s making an effort for yourself the same way you’d make an effort for someone you’re dating.


Why dating yourself is a powerful form of self-care

It’s easy to get hung up on self-care as it applies to physical wellbeing; nutrition, exercise, sleep and so on. Dating yourself ticks the other self-care boxes, like mental and emotional health. Taking yourself on regular dates can:


  • Boost your self-confidence
  • Strengthen your sense of self
  • Increase your self-love and self-respect
  • Make you comfortable with solitude
  • Uncover new interests 
  • Help you establish healthy standards and boundaries for relationships with others

The dos and don’ts of dating yourself

Flopping onto the couch for another marathon session of Friends reruns does not count as a date. To turn solo time into self-care time, follow these dos and don’ts:


    • Don’t invite a friend. This is not a double-date. Dating yourself means spending time alone.

    • Do plan ahead. Like you would for a regular date. Research events in your city, buzzed-about restaurants, the coziest bars and what’s on at museums and galleries. Pick a date, set a time, buy tickets and get excited.

  • Don’t bail. Treat a date with yourself like a date with somebody else. Add it to your calendar and make it a priority.

  • Do show up for yourself. Wear the dress, the suit, the lipstick—whatever you’d do on a date with someone you’re interested in. Impress yourself.

  • Don’t rush. Stay present and enjoy the moment. Be mindful of what you’re thinking and feeling. This is a chance to get to know yourself better and strengthen your connection to your inner self; take advantage.

  • Ideas for first dates to take yourself on

    Dating yourself is a chance to do, see and eat exactly what you’re interested in, without considering anyone else’s wants, needs, budgets or dietary restrictions. Here are a few beginner-friendly ideas for self-dates:


  • See a movie. A dimly lit room where no one talks to one another and you can eat candy by the handful free of judgment? Taking yourself to the movies is the first solo-date you should try to ease into the self-love club. Take this opportunity to see the movie you actually want to see, for no other reason than pure popcorn-fuelled pleasure—whether that’s the cheesy rom-com, the superhero sequel, or the heady, subtitled foreign film.

  • Take a class. Cooking classes and wine-and-paint nights aren’t just for lovers. If you’ve always wanted to try something, try it. If you end up digging it, challenge yourself to sign up for a recurring class so you can keep the (self) love alive.

  • Wine and dine yourself. Yes, you can make a reservation for one. Order exactly what you want off the menu and savour every bite without worrying about sauce on your lip or your pasta-twirling skills. Bring a book as back-up if you start feeling uncomfortable—just challenge yourself to stay off your phone (the endless Instagram scroll as a first-instinct coping mechanism is one self-date habit to kick to the curb).

  • Whisk yourself away. Treat yourself; a night alone at an upscale hotel is completely indulgent and entirely worth it. Get the room service, wear the robe and sprawl out across the king-sized feathertop. If you want to save some dollars, use the app Hotel Tonight to find a deal or Google hotels in your city that have post-3pm discounts for same-night bookings (like the gorgeous The Annex Hotel in Toronto). You deserve it.
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