September 12, 2023

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When I was in high school, there was a girl in my youth group who was popular, and I was convinced she hated me. (I’ll call her Ashley.) I tolerated her presence, but I resented her for “stealing” my friends when they’d prefer to hang out with her over me. I resented her for never inviting me to things. I wondered what I did wrong to make her hate me. I would’ve wanted to be friends if she wanted to.

But several years after high school, after she had gotten married and had a few kids, we actually had a heart-to-heart. I said, “Ashley, I need to be honest. I always thought you hated me in high school.” She looked at me with the widest eyes and said, “Oh gosh, Vania, I never hated you. I thought you were too cool to be friends with me.” Shocked, I said, “I wanted to be friends with you though! So you mean, this whole time, we could’ve been friends??”

A slightly awkward, honest conversation in high school would’ve cleared everything up, and I would’ve had a great friend (and been invited to the parties). But my aversion to conflict kept me from addressing it head-on.

As I’ve gotten older, I’m less averse to the messy, honest, spit-out-the-truth, ask-all-the-questions, Awkward Conversation. In fact, I try to do that more when necessary, and I always respect someone who musters the courage to initiate it with me. I always make a safe space for that. More often than not, there’s an open door of possibility on the other side of the conversation. There’s much-needed clarity on the other side. And we all become that much more mature on the other side.

So if you find yourself stuck in a situation where the only potential solution is an awkward conversation, here are some tips:

  • The first awkward conversation to have is the one with yourself. Do whatever it takes to get clarity on yourself. What mistakes do you need to own up to? What is the story you’re telling yourself? What’s the story you’ve been telling yourself about the other person? What clarity or closure do you need from the other person?
  • If you believe in the Bible, be VERY intentional about asking God for wisdom. And believe without a doubt that He’ll answer you. You have this promise in James 1:5-8: “If any of you lacks wisdom, you should ask God, who gives generously to all without finding fault, and it will be given to you. But when you ask, you must believe and not doubt, because the one who doubts is like a wave of the sea, blown and tossed by the wind. That person should not expect to receive anything from the Lord. Such a person is double-minded and unstable in all they do.”
  • It’s possible that wisdom may come through a mentor. Find the type of person you aspire to be. If you want healthy relationships, find someone with good character who has a track record of having healthy relationships. Avoid well-meaning friends with fractured relationships.
  • Finally, don’t be afraid. Have the conversation. Depending on your situation (and the wisdom you get from God and/or a mentor), the conversation may start like this: “Hey, could we talk? I need to get something off my chest” or “I could really use some clarity and closure on something.”

The points at which we mature as adults are the ones where we go through the uncomfortable things, not just try to get around them. Think of childbirth; human life literally doesn’t come into being without a painful mess, but the result is worth it.

Also, keep in mind that an awkward conversation is not nearly as painful as childbirth, so just go ahead and send that text. 😉

About the Author

Vania Hardy is an artist, illustrator, and designer who loves helping people find their creative uniqueness and create inspiring spaces in which to live, work, and thrive. Her bodies of work include painted acrylic pieces on canvas, an array of illustrated children's books, and small business branding.

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