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Confessions of an Awkward Dater

woman smiling
Maybe we're making this dating thing a lot harder than it has to be.

In uncomfortable social settings, my nerves take over, causing a visceral reaction of nausea and over-sharing. So basically I’m a pro at dating.

I am not known for my ability to remain calm under pressure, particularly when that pressure involves dating. As we all know, girls who overshare on the first date rarely get the guy. However, I’m convinced that dating can still be productive, not to mention fun, for those of us who are hopelessly awkward.


I once met an attractive, bearded hipster on an online dating website. We emailed back and forth for months until we decided it was time to meet in person. I had never been on a date with someone I didn’t know in real life, so my anxiety was through the roof. I thought through every scenario for our first face-to-face interaction. Should I shake his hand? Give him a hug? A high five? And then there was the issue of conversation. We had spent months emailing about our lives, and I was afraid we would have nothing left to say when we finally saw each other.

Much to my dismay, date day arrived without any sign of Jesus’ return. I carefully picked a cute outfit that would not easily show sweat stains, and I made my way to the agreed-upon coffee shop. As soon as I spotted Bearded Hipster inside, the thought of making eye contact felt like trying to climb Mt. Everest. I got out of my car and immediately lost the ability to speak or act like a human being. Instead of greeting this man like a normal person, I let out a gruff, manly chuckle and walked right past him.

My roommate had also convinced me to bring a book that contained conversation-starting questions. Once we got inside the coffee shop and sat down with our drinks, I suggested to Bearded Hipster that we each pick three questions to ask the other person. I went first, opening at random to question 93. As I read the question aloud, my face turned beet red and my cute outfit could no longer hide the sweat. Question 93 was about sexual purity. With wide eyes, Bearded Hipster suggested we put the book away.

It was the worst date of my life. But for some reason, Bearded Hipster had mercy on me, asked me out on a second date, and then another and another. We have been married for almost four years now, and that’s one reason I know God is real.

Here’s the truth – dating is hard. It can feel awkward and uncomfortable. There’s so much pressure to get every move right, especially at that first meeting. But maybe we’re making this dating thing a lot harder than it has to be. Maybe this process can actually be a little bit of fun. Here are some tips and tricks to reclaim dating for the socially clumsy.

1. Be you.

This sounds trivial and obvious, but it’s the foundation of a fun dating experience. Be the kind of person who is comfortable in their own skin, who can laugh at themself, and who isn’t afraid to look silly. Psalm 139 reminds us that we are fearfully and wonderfully made. I used to read that passage and immediately apply it to my physical makeup, but I think it applies to something deeper as well.

Psalm 139:13 says, “For you formed my inward parts.” God made you just the way you are – inside and outside. He knows the number of hairs on your head and the number of thoughts in your brain. Own your off-beat sense of humor or your slight obsession with Lord of the Rings. You can have confidence in all of you — your looks, your intellect, your personality — because that’s exactly how God made you.

2. Be gracious.

Grace is disarming, and it’s something we’ll all need at some point. When Bearded Hipster extended grace to me after our first date, it allowed me to relax. Proverbs 16:24 says, “Gracious words are like a honeycomb, sweetness to the soul and health to the body.” Instead of flattery or false affirmations, we need to be speaking words of genuine encouragement and grace to the people we are dating. As strange as it may be, consider how you can use your words to love the other person. All communication has power, and it will set the tone for your entire dating experience.

3. Be honest.

Dating has a way of tempting us to exaggerate our strengths and minimize our weaknesses. It makes sense because we all want to put our best foot forward with our romantic interests. But the façade has to come down at some point. Remove any cause for stress later on by telling the truth about your life from the beginning.

This doesn’t mean you have to confess sin and share life stories on the first date (in fact, this sounds like a horrible idea), but if you win people over by being something you’re not, you’ll live in fear of them leaving you once they discover the truth. Be forthcoming about your own struggles and opinions, and don’t go out and buy a Cubs hat just because he mentioned something about loving the team and you blurted out “Me too!” before thinking. You are worth loving and getting to know—the person you pretend to be is not.

4. Be rooted.

The dating game always made me hyper-aware of my insecurities. It’s scary to put yourself out there and face potential rejection, which is why we have to be grounded in who we are. In Isaiah 61, you and I are called “oaks of righteousness.” And do you know what happens to oaks of righteousness? Isaiah 61:3 paints a picture of joy and freedom for those of us who are rooted in the Lord. This revelation will change the way you date because a life rooted in God is a life that’s full and free.

It’s taken me a long time to feel comfortable in my own skin — to celebrate and even lean into my awkward tendencies. Relationships are meant to sharpen us and lead us into maturity, and if I need people in my life who are extroverted and creative and laid-back, then maybe they also need someone who is endearingly awkward. I have spent years trying to cover up certain parts of my personality because I thought they were unattractive. I didn’t want to be the girl with sweaty palms, a fear of eye contact, and a tendency to over-share. I envied those who could fill a room with their contagious laughter, tell engaging stories with ease, and appear relaxed around perfect strangers. My awkwardness was my greatest weakness, or so I thought.

One day, after a particularly embarrassing social incident, Bearded Hipster told me that he finds my awkwardness attractive. I couldn’t believe it! The thing I viewed as the biggest flaw in my personality was actually part of what drew this man to me.

It’s amazing that we can walk through life trying to cover up the very things that have the potential to draw love out of another person. The thing that I see as a blemish, others may very well see as beauty.  Oftentimes our awkwardness or our introversion or our outrageously loud laugh is the truest and most beautiful thing about us. And maybe those things are not meant to be hidden — maybe they’re meant to be celebrated.

Copyright 2016 Maggie Johnson. All rights reserved.

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About the Author

Maggie Johnson

Maggie Johnson is a social justice junkie who lives with her bearded, worship-leading husband in Indianapolis. As a feisty introvert, Maggie is allergic to large crowds, first impressions, and small talk. She’d much rather sit down one-on-one at the local coffee shop to hear your story. She’s a fan of theology, the local church, a good cup of coffee, and she believes that no one is past the point of grace. You can find her on Twitter by following @maghjohnson.


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