Learning To Date Yourself

The other day I took myself on a date.

I had to ask myself out ahead of time because I like to play hard to get. I asked myself out on Sunday for the following Sunday. I told myself not to make plans because I was going out. I went to church and walked the dog around Midtown before heading to the movies. I saw a movie and then went to Chipotle where I sat alone and read a book. Then I saw another movie.

We had a lovely time, myself and I. In fact, it was one of the best dates I’ve ever been on.

I bet if you saw me at the movies or at Chipotle alone you would’ve pitied me. You would’ve thought I didn’t have any friends or that I’m really lonely. But you would’ve been wrong. I wasn’t lonely at all. Sure, I was alone, but I wasn’t lonely. There’s actually quite a difference between the two.

In fact, I’m learning that quite often I’m loneliest when I’m in a crowded room. I’ve discovered that being around people doesn’t really cure my loneliness. Loneliness is a state of being not contingent upon the presence of others. It’s more of an internal thing and less of an external thing.

You can be alone without being lonely. You can be lonely without being alone. They aren’t mutually exclusive.

But back to my date with myself.

Learning to date myself might be the best thing I’ve ever done.

It’s just like dating another person. I’m learning how to get to know myself the same way I would get to know anyone else. Taking myself on dates forces me to connect with the parts of me that I’m very good at avoiding during the week. It causes me to slow down and have a genuine and intimate conversation. It helps me check in and see how I’m doing. I get to ask myself questions I don’t seem to have time for or would simply rather avoid.

Being alone helps us discover who we really are.

And being alone is terrifying. Trust me. Whenever I ask myself on a date I’m always very tempted to cancel. It’s easy to want to overbook or reschedule.

But if I’m not willing to invest in myself then how can I expect anyone else to invest in me?

Think about a good project. Someone casts a vision and sees the possibility of something different, something better, something more. They pitch the project to investors. If there’s a solid vision with a lot of good potential then people are very likely to invest. They’re more inclined to commit to something when there’s a vision and direction.

People are just works in progress.

I’m a project. Without a vision or some goals I’m just a really lousy blueprint that’s not going anywhere. I can’t go sit down across from some people and expect them to invest in me if I haven’t taken the time to invest in myself. And I can’t genuinely invest in myself if I don’t spend time investing myself.

If we don’t think we’re worth choosing then we can’t expect others to do the same. We’ll sit down across from people with a lot of social capital, people who we admire and respect, and we’ll ask them to invest in us. But if we aren’t willing to lay the foundation and cast the vision for the completed projects we would like to be then we’re just draining their resources. We’re wasting their time, their relationship, and their expertise. They could go invest in a person/project that’s actually going somewhere and doing something.

You’re worth choosing. You’re worth investing in. But you’ve got to start choosing and investing in yourself before you can ask others to do the same.

If you aren’t willing to make that commitment to yourself then you’re going to drain your relationships. You’re going to ask them to keep pouring into you but it’ll never be enough to really build something or get somewhere.

People are more inclined to invest, financially or relationally, in people who do their research.

Do your research. Get to know yourself. Ask yourself on some dates and spend time with yourself. Seriously, the best way to research yourself is to be alone with yourself.

What do you like to do? What helps you connect or re-energizes you? What inspires you? What makes you want to go create something? What brings about the tough questions in you? What are you good at? What are you not so good at?

You might think it's selfish to invest in yourself. I think it would be selfish if you didn't. What will the world miss out on because you didn't know yourself enough to explore who you truly are? What novel will go unpublished? What song won't be written? What business won't be started?

Sign up for that class. Register for the conference. Go get your nails done. See a movie. Drink the fancy coffee. Book the flight. Order your favorite dish and get the best cocktail. If you can’t spend money then go on a walk. Read a book. Sit outside. Go to the park.

You owe it to yourself and to others to start investing in yourself.

When you do, I promise you’ll see a return on your investment. You’re going to see your relational capital grow. You’ll be more creative because you actually know yourself and can connect with yourself and therefore with others. You’ll be more likely to turn away commitments or people who will bleed you dry because they aren’t willing to make their own investments. You’ll be able to say yes to what’s important and no to what’s unnecessary.

I would also like to say that I’m free to invest in myself because I have an unlimited resource in Christ. He invested in me first. He chose me when I was unwilling to choose myself. He relentlessly chooses me every single day. Because I’m chosen in Christ I’m therefore able to choose myself risk-free.

Be brave and ask yourself out this week. It'll be awkward at first but just like dating it gets easier and easier to say yes. Maybe one day you'll actually look forward to spending time with yourself. 

Maybe, just maybe, you'll learn to love yourself along the way.