January: a Month in Online Dates

[Cara Strickland’s guest post today makes me glad in so many ways. I’m glad for her gifted story-telling, I’m glad she consented to write this up after I practically begged her to expand on her tweets about her January date-life, and I’m glad dating is no longer my scene.]


I’ve always hated dating.

I’m usually breathlessly nervous beforehand, with a sick feeling in my stomach. I remember one experience very well. I was sitting in the parking lot of one of my favorite restaurants, preparing to go inside to meet someone. We had met through friends and he’d asked me out. He’d been earnest in his interest, he’d done everything right. But as I sat in that parking lot, I didn’t want to go inside. “If you ever want to get married,” I said to myself, aloud, “You have to do this.”

That experience did not end in bliss, and there were many more like it, evenings and weekend days of tension, small talk, and worry. Like nearly everyone who manages to remain single past the age of twenty-two (and eventually wants to find someone to share a life with) people started to ask if I had thought about dating online.

In our culture of billboards, radio ads, and happily married friends, I certainly couldn’t escape thinking about it.

I tried eHarmony, and went on one single, dreadful date, allowing my membership to go by without more interaction. But at the end of 2014, I was feeling differently about dating. I wanted to be brave with my life, to go out to dinner, to learn that it was possible to have a pleasant conversation with a stranger. Late in the fall, I read a poem by Elizabeth Austen called “The Girl Who Goes Alone” that captured my imagination. The last line reads: The girl who goes alone says with her body/ the world is worth the risk. (You can hear Elizabeth read the whole poem here) I wanted to be that girl. I wanted to take the risk.

In late December, I joined Tinder, a free dating app. Most people know it as the app that facilitates hook ups, but a friend who had met a long term significant other through Tinder urged me to give it a shot. Although I was nervous, I began to say with my body, my words, and my free time: the world is worth the risk.

I went on five dates in January, more than I had been on in the previous two years combined. May they make you sigh, giggle, and give you hope. Names have been changed to protect the innocent, and the guilty.

I. Drew

I hit the green heart because he had an artsy picture. It’s his silhouette in the sunset in California. His bio tells me that he’s a writer, too, interested in film, music and books.

We match.

I text him for the first time in the middle of a snow storm. He is in town short-term, working long days for a construction company and making music in his hotel room at night.

We have quite a bit in common, and for the first time in a long time, I’m excited about the idea of meeting someone.

What would you want to do if we met up? he asked.

Get coffee, walk around a bookstore? I replied.

We met at Barnes and Noble after work one evening. I took my place, waiting in the “F’” section in general fiction, where John Fante would have been if they’d had any of his books.

He saw me and turned. “Are you Cara?” he asked, hand extended to shake. “I’m Drew.”

We walked to the Dr. Seuss section, talking easily, but with nerves just under the surface. Slowly, we made our way across the store and ordered cups of tea, sitting at a small table.

By now, I was completely at ease, still pinching myself that I was on a date and that it was fun.

We talked frankly about our other Tinder matches, and about how we felt our date was going. (This might not be everyone’s cup of tea, but it totally worked for me). At one point, we stopped and told each other how we were coming across. I was in Heaven.

Before the date ended, he asked for my number, then texted me his. I drove home, thinking that maybe this wouldn’t be so bad after all.

II. Brad

I agreed to go out with him because he seemed funny over text.

I’d told him my rule about not giving out my number before meeting someone, he stopped texting back as quickly, after that. When I asked him if he’d lost interest because I wouldn’t share my digits, he responded with: Oh totally. I returned the ring today.

Dinner could be fun, I thought.

I arrived at the restaurant a few minutes early and waited in my car, watching the snow fall. He texted me shortly before we were supposed to meet. I’m going to be a few minutes late.

Half an hour later, he showed up. My feet were freezing in my knee high boots. I prepared to smile pleasantly.

The date went downhill from there.

I’ll share this favorite tidbit, and leave the rest to your imagination.

He began to talk about being an over thinker.

“I relate to that,” I said.

“Yeah, I sort of thought you might,” he said.

I paused, counting slowly in my head before responding. “What makes you say that?” I asked.

“Well, when I asked you where you wanted to go to dinner, you asked what my price range was.”

“I don’t know your financial situation,” I said. “I wouldn’t have wanted you to be someplace you were uncomfortable.”

“So, do you expect me to pay for this?” he asked.

I counted again. “No,” I said. “But I wouldn’t want someone to put me in that position.”

Somehow, the waiter seemed under the impression that we were having a swell time and left us alone. I snuck away to the bathroom near the end (almost three hours into the date) and texted Drew; I’d told him about this Tinder match. This date is not going well.

I’m sorry. He responded, within a moment.

I walked back to the table and told Brad that I needed to go to church in the morning. We parted with something resembling a hug.

III. Drew

As soon as I got in my car, I texted Drew. Do you want to get a drink?

I swung by his hotel to pick him up, and we decided to head back to the same restaurant. As I entered, the host looked at me strangely and asked me if I had forgotten something. As we took our seats at the bar, my waiter made pointed eye contact (as did some of the other wait staff).

Drew and I debriefed, getting rid of the bad taste in my mouth with a little good conversation. “On to the next one,” he said. “Sure dating is hard, but it can be so worth it.”

I drove him back to his hotel and then headed home, my heart lighter.

IV. Carl

Carl and I met at a local coffee shop. He was nervous and shy, speaking quickly. Almost immediately, I knew that we had little more in common than our hometown and personhood. Still, I’m learning that there is always something to learn, if I’m paying attention.

We talked about food, and food writing. He told me his favorite restaurants in town. As he spoke, I watched him relax. He was nice, and loneliness hung over him like a worn sweater. I found myself rooting for him to find someone.

“So, do you want to go out again?” he asked, just as we parted.

“Let me get back to you,” I said, unwilling to turn him down on the spot.

The next day, I let him down easily, over text. He offered his assistance if I should need help with food reviews.

V. Chase

January drew to a close and it looked like there would be time for one last date.

Chase and I started talking just after we’d had to put my family dog to sleep. I was a mess and it was all I could think about. Even though I spent our first conversation essentially eulogizing my dog, he kept texting me.

We planned to go to a hockey game together. (Which is my idea of a great date).

I waited for him outside the arena. I’d found a nearby parking spot, and walked through the cold, my hands shaking, just a little.

I knew him as soon as I saw him, and we began walking toward each other.

I can’t explain why, or how, but as we fell into step, talking and beginning to look for our seats, something in me relaxed. Not a trace of nerves remained.

The game was wildly entertaining. Though our team didn’t score a single goal, there were four fist fights on ice. Chase and I vacillated between silence and conversation. I began trying to make him laugh after I heard it for the first time, hearty and rich.

As I sat in the warm, familiar arena, I realized that what I’d hoped for had come to pass. I wasn’t scared of dating anymore.

We had made our peace.


[Cara Strickland is a writer, editor, and food critic in Spokane, Washington. She writes about singleness, food, feminism, and the way faith intersects life (among other things) on her blog Little Did She Know

Come say hi to her on Twitter or Facebook. She likes making new friends.]

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6 Responses to January: a Month in Online Dates

  1. Jeannie says:

    Thanks for taking us with you on these dates, Cara! 🙂 Like Tim said, I’m glad my dating days are behind me. Actually I don’t remember that I had very many dating days. But these vignettes you shared are a good reminder of how much kindness and courage and hope we need to try new things, make new connections, move our lives forward. I really enjoyed this.

  2. Tim says:

    Cara, you showed good humor and great kindness to those guys you dated. I am betting that the way you handled those dates is a good indication of the care and kindness you put into your friendships long term too. Thanks for sharing your January with us.

  3. Pastor Bob says:

    Dating – – pluses and minuses to this activity, some if it ritualistic, some of it habit, some parts not needed. Wishing you well in your ventures.

  4. Aimee Byrd says:

    This topic really intrigues me. It seems dating is much more difficult for singles these days. It has become a status instead of an event (especially with the younger crowd). Or, in Christians circles, it is so weighty, like if you ask someone to dinner you are practically ready to meet their father. I love how you have been able to casually get to know some different people in an appropriate way. Thanks for sharing.

  5. You’ve almost convinced me to join Tinder now. 😀

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