Dating Myself

I’ve become the butt of a joke among my friends: move in with Beth, be married within a year. But the thing is it’s true. Every year since 2008, I have moved in with a totally single roommate, and within that year she would be engaged, married, and moving out. I kid you not, this happened with six roommates in perfect succession. It started off as a very joyful season, being able to be part of my friends’ lives in that way. But after a while, it wasn’t funny anymore. My heart became deeply discontent, bitter, envious. I felt like I was missing out on all the fullness life had to offer. I began to idolize marriage in pretty unhealthy ways, which was obviously not God’s intent for my heart. I had to let the Lord work on some extremely tender wounds to get to where I am now.

I moved to Chicago right after college, and I really enjoyed the first few years of being single, largely because many of my friends were single as well. We had a blast going out for dinners, having girls’ nights in with sweatpants and pizza, and enjoying summer days at the beach. We spent hours at a time laughing and talking and dreaming. It was the stuff cheesy movies are made of, and we watched plenty of them.

As time went by, though, many of my friends started dating, then getting engaged, then getting married. The fact that social media makes everyone’s big life changes seem so perfect and in-your-face (thanks to a constant stream of ring photos and wedding countdowns) made me feel like I was suffering from a serious case of FOMO (Fear of Missing Out). I couldn’t help but wonder, When will it be my turn? There were certainly moments of peace and joy throughout this time, but more often than not, I felt like a spinster compared to my married friends. I experienced a lot of loneliness, feelings of abandonment, and actual periods of grief over some of my friendships. I knew my dear friends would always be in my life, but our relationships changed when they got married. While I understood that would happen, it didn’t exactly make it easy to deal with.

The truth is I would have sacrificed just about anything to have what my friends had. I couldn’t help but wonder when it would be my turn to go apple picking with my own guy, walk hand in hand to that new restaurant down the street, or cuddle up with some hot chocolate and a movie on a cold night. I wanted to post a “this is my surprised face because I’m getting married and here’s my ring to prove it” picture. Okay, we all know it’s not about the ring and the pictures, but, come on, it must be so much fun to wear that perfect outfit in your outdoor fall engagement session, playing in the leaves, and knowing you really are as in love as you look.

Then it hit me: Why should I have to wait for a man to do these things? Well, for obvious reasons I would have to wait on the ring picture because, hello, crazy lady. The rest I could do, though. I decided to start dating myself.

The Start of Something New

About a year ago, I finally realized all the negative feelings I had about my singleness were just dragging me down, and I was the only one who could change this. I grew tired of feeling envious and wallowing in self-pity. I decided to take action by spending intentional time with myself doing what I wanted to do, and my hope was that the feelings of contentment would follow.

I know you may be thinking I should be content in God alone, Christ is enough, and he is my identity. I wholeheartedly believe all that, but to be honest, those phrases often get thrown around carelessly in Christian circles. I realized I needed to discover my own identity in Christ, learn to love who he created me to be, and discover more about who he wants me to be in the future. And I knew I would only be able to do that by seeking some time with myself. Not just by myself, but with myself.

The practice of dating myself has become critical in helping me re-center my heart over and over again on Christ and his work in my life. And with no one else around that I’m trying to please, I can be exactly who I am without fear. If I take myself to a movie, I can get extra butter on my popcorn without needing to explain myself because, hey—no one’s judging me! If I want to dance around my apartment lip-syncing to Mariah Carey, I can do it without feeling an ounce of shame. And when I ask myself the tough questions, I can be totally honest because God already knows what I’m thinking. He’s never surprised by me. What a relief it is to not feel the need to impress the person across the table.

The Logistics

I try to take myself on a date once a month. I set a budget and follow a couple ground rules. First, I don’t allow myself any crutches when I’m out at dinner. No looking at my phone, no reading a book, no hiding behind something that will make me feel more “okay” with being alone. It took a while to get used to the surprised look on a server’s face when I told her that I was not, in fact, waiting for anyone else. I had to learn to tune out other people’s worried glances as they wondered if I had been stood up.

Second, I ask myself honest questions—and I provide honest answers:

• How am I doing at being content with who I am? Do I like who I am and who I’m becoming? What changes need to happen in order for me to keep becoming more like Christ?
• How am I doing at loving God? Family? Coworkers? Enemies?
• Have I been a good friend this month? Is there a specific friend I need to be more intentional with?
• How am I doing with my finances? Saving? Spending? Paying bills?
• What has been the most joyful moment of the past month? What has been the hardest moment? And what can I learn from that?

How You Can Date Yourself

Here are a few tips for making this practice work for you:

Be intentional. Schedule the date night. Put it in your calendar, and don’t cancel or move it for anything. If you wouldn’t flake out on a night with a dear friend, then why would you deserve less from yourself?

Leave the distractions at home. Don’t take a phone or book with you. If you’re an external processor, you may want to bring a notebook and a pen so you can reflect on the above questions in writing, but don’t bring anything you’ll attempt to hide behind or that could distract you from your time with God and yourself.

Get over your fears. At first, you’ll probably feel the temptation to make it look like you’re waiting for someone to arrive, rather than just being okay being by yourself. Don’t be afraid to say you’re just celebrating a night out! One time a server told me she was encouraged by my example—that a woman could be so independent, free, and secure.

Just enjoy. Yes, I ask myself serious questions to “check in” because that’s what healthy couples do. But at the same time, it’s okay to relax and have fun! Take yourself out for a manicure, see that new Ryan Gosling movie, treat yourself to ice cream on your way home—do something that’s special for you.

An Act of Faith

Dating myself has caused me to draw closer to God because it helps me not to feel so empty in my singleness. It’s just so easy to blame God for what I believe is missing in my life. But when I seek fulfillment on my own—not in myself but in the Lord—I can come to him with a more grateful and honest heart, because I’ve taken the time to really reflect on how he’s shaping me, how I’ve failed, how he’s shone through me, and how I’m growing.

Ultimately, my faith is the reason I do this. I don’t want to be someone who doesn’t take care of herself and doesn’t seek to grow in love. Scripture says our love will prove to the world that we are disciples of Jesus (John 13:35), so shouldn’t you also work on loving yourself? Develop a lifestyle of pursuing Christ, others, and yourself that is deeply satisfying. Take yourself out on a date. You deserve it.

Beth Hobson is a paralegal at Segal McCambridge, and she lives in Rogers Park, Chicago.

Read more articles that highlight writing by Christian women at ChristianityToday.com/Women