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How to Date Yourself

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Dating can be really fun: you’re invited into the minds and worlds of fascinating people and learn a great deal about yourself in the process. There’s an excitement to falling in love too that’s hard to find elsewhere, which makes becoming a serial monogamist all too easy.

I heard the term “serial monogamy” for the first time a few years ago, which describes the process of continually engaging in back-to-back monogamous relationships. While this might be a powerful antidote to loneliness for some people, it can also contribute to a great deal of internal emotional confusion. As we continually latch onto others, we can lose sight of our own values, wants, needs, boundaries, and more. To break this cycle, I invite people to stop dating others and instead take some time to date themselves instead.

Essentially, this means going through the usual stages of a romantic relationship but replacing the love from another person with love for yourself. In today's post, I break down what this means and how to do it yourself.

1. Scan for deal breakers.  

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Whenever we start dating someone, we tend to keep a mental “checklist” that directs our future actions. As we discover a person’s quirks, we’re forced to identify which of them are deal breakers and which of them aren’t. And when we’re okay with the majority of these quirks, well I guess we call that “love.”  

Dating yourself means going through this exact same process. It means taking a good, hard look at yourself and asking, “Would I want to date me with all of the qualities I have? Which of my qualities are deal breakers?”

I’ll use myself as an example. In addition to the obvious list of dealbreakers like being a cheater, jerk, or psychopath, my dealbreakers include: insecurity/lack of confidence, unwillingness to engage in thought-provoking conversations, no sense of humour, and a lack of hobbies, interests, and friends. So if I were going to make a relationship work with myself, it would mean making sure I don’t have any of the deal breakers on the list either. Am I confident or do I constantly put myself and look for external validation? Do I open myself up to the opinions of others even if they're different from my own? Do I possess the ability to laugh about this crazy thing called life rather than taking everything so seriously? (You get the picture.)

2. Get to know the person’s world.

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Once you’ve concluded that the person doesn’t have any obvious red flags, it’s time for the fun part of dating: getting to know them! What kinds of hobbies do they have? What are their friends like? How do they act in different situations? This is an exciting process of discovery as we continue to unearth their values, beliefs, and more.

And yet, in a world as fast-paced as ours, it can be all too easy to lose sight of our own values, beliefs, hobbies, etc. And when we’re constantly bouncing from one relationship to the next, it’s possible that a fascination with the values and beliefs of others transforms into a process of unconsciously adopting those values and beliefs ourselves.

Take a minute to evaluate and reconnect with what’s important to you as an individual and pay attention to if you’re enacting these values in your everyday life. If you aren’t, what needs to be added into your life to allow for this to happen?

3. Meet the friends and family.

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When we feel like a relationship with someone is starting to get serious, we typically invite them into the more personal, private world of meeting our family members. In the context of dating yourself, this means reconnecting with the family members with whom you maybe haven’t made much time for recently. What have they been up to? What’s new in their lives? What might you want to share with them, too? So, take the time to reconnect with all of the important people in your life.

4. Explore being intimate.

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It’s not uncommon for women to tell me that they aren’t particularly sure what they like or dislike during sex. I attribute this to two things: harmful messages being perpetuated by pornography and patriarchy. Due to these two factors, it’s very easy for sex to become a male-centred act in heterosexual couples where the woman’s job is to please her male partner.

When it comes to dating yourself, it’s important to not only reconnect with your likes and dislikes during sex, but also your boundaries around different sexual acts. When do you feel most comfortable having sex with someone? Do you even feel comfortable having sex at all? How might you be able to articulate your sexual needs in the future? Are there times when someone has crossed a sexual line in the past? What boundaries do you need to set up in the future to ensure that that doesn’t happen again?

5. Acceptance and maintenance.

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There comes a point in any relationship where the honeymoon phase ends and we’re confronted with the harsh reality that we are in a relationship with an imperfect person. At this point we have a choice: are we going to end the relationship and see what else is out there or are the person’s flaws inconsequential enough that a certain level of happiness can be upheld? If we choose the latter option, what we’re really doing is practicing acceptance: I accept that you’re an imperfect human who’s going to piss me off every now and again because I acknowledge that the good parts of you—and our relationship—outweigh the bad. Couples typically experience a great deal of conflict when they’re unable to practice this acceptance and spend their energy trying to change the other person instead.

When it comes to dating yourself, it’s important that you also reach a point of accepting your own flaws—maybe even appreciating or loving them. So many of us continually beat ourselves up rather than practicing acceptance and self-love. We’ll say things like: I shouldn’t have gotten so emotional at work today. I’m such a fat slob for gaining 10 pounds. I’m such an idiot for making a mistake on that report. If you wouldn’t say any of these things to another person, you shouldn’t be saying them to yourself. End of story. This is a form of inner emotional violence that needs to stop.

The Bottom Line

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There are so many roles that we occupy on a daily basis. We’re employees, daughters, sons, co-workers, brothers, sisters, cousins, boyfriends, girlfriends, friends, lovers, and the list goes on. But sometimes we focus so much of our attention on romantic relationships that we forget to look at the most important relationship in our lives: the one with ourselves. In order to give anything to anyone you need to be able to stand on your own two feet first. So be your own significant other. Buy yourself flowers. Do something thoughtful for yourself to put a smile on your own face. Tell yourself you’re handsome or beautiful every now and again. Treat yoself. All those things you love in a significant other? Be that person for yourself. Because hey, you’re stuck with you forever so let’s make this relationship as great as it can be.


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