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How to Make a First Date “Ask” Less Awkward

Whether you’re asking someone out or rejecting someone you don’t want to hurt, there are good ways – and poor ways – to express your feelings.

I’ve been asked out twice, and both times I wish the situation had gone differently. No, I didn’t laugh in either guy’s face or run away screaming. In fact, we were all very polite. Too polite. Polite quickly became awkward, and both encounters ended poorly.

These memories are a bit embarrassing to reflect upon, but if I don’t, I’ll never learn from them. What went wrong? Put simply, none of us knew how to properly express our feelings to the other. I’ve since come up with two things that both men and women must do to ensure healthy communication in a dating “ask.”

Speak with conviction.

The first time I was asked out was on a bus after a college trip to a MercyMe concert. Well, I say he asked me out. What he really said was, “So, I like you. I don’t know what you want to do with that…” He was right; I didn’t know what to do with that.

It was his lack of conviction that irritated me. If he were serious about liking me, he would have asked me out or at least asked me how I felt about him. Instead, he left the ball in my court and made me decide “what to do” with his feelings. That struck me as immature and directionless, two qualities I wasn’t looking for in a boyfriend, let alone a husband. I told him I wasn’t interested, and that was the end of the discussion.

When asking someone out, make sure you’re in fact posing a question. Do you want to go on a date? Do you want to get to know her better? Are you wondering if she reciprocates your feelings? If you’re not sure what you want, she won’t know either, and you risk losing a relationship before one ever begins.

On the receiving side, you should be willing to express (or at least consider) your feelings about a potential date. In my case, I already had a hunch this guy was interested. I knew I wasn’t, so his manner of asking only confirmed that. You may not know how you feel about someone, especially if the option to date comes as a surprise. Just be sure to give a straight answer, even if it’s, “I don’t know.” If the latter, promise to circle back soon with something more definite. Then follow through. Which brings me to my next communication principle:

Be clear.

The second guy, a year after the first, asked me out properly after a concert on campus. (What is it with guys asking me out after concerts?) I declined to go on a date with him, and he then asked if I might ever change my answer.

I wasn’t sure how to tell him that no, I wasn’t going to change my mind, because that sounded rude in my head. So, I made up an excuse about it being finals week and not wanting to start a long-distance relationship over the summer and my semester abroad in the fall.

What’s missing from my reply? I never told him no. So over the next eight months, he texted me on a weekly basis, sometimes more frequently, while I tried to rationalize away his attention by pretending he was just being friendly. I knew better, yet I never took the necessary and mature step to give him a definitive answer.

I finally saw him again in December at (you guessed it) a concert. He clearly wanted to talk to me, but I avoided him until the next day when I finally decided this ambiguity couldn’t continue. He asked me again if I would ever date him and I told him I wouldn’t, something I should have done months prior. He was disappointed, but glad I finally gave him an answer.

We wouldn’t have had those months of awkward back-and-forth if I had just told him clearly what I was thinking in the first place. Instead, I left him to read my mind and actions, and rationalize them into whatever he wanted them to be.

With communication comes character

Speaking with clarity and conviction about your feelings, whether asking or replying, isn’t just good communication; it displays good character. Are you more likely to want to date someone who asks you out with confidence or hesitation? Would you pursue someone who can’t give a straight answer?

Telling someone what you’re truly feeling and thinking about any relationship potential treats them with the respect you’d like to be given. And even if it’s a no, they’ll appreciate that you didn’t beat around the bush.

Copyright 2023 Katie Stoneback. All rights reserved. 

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About the Author

Katie Stoneback

Katie Stoneback is a recent graduate of Geneva College with a Bachelor of Arts in writing and Spanish. She lives in Pennsylvania, but loves to travel and explore new places and cultures. Recently, she has been trying her hand at playwriting, and her first show will be performed by her high school. She’s excited to see how God will continue to use the literary gifts He’s given her.

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