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5 Dating Mistakes I’m Guilty Of

a woman and man on a date, the woman seems displeased and like there have been some dating mistakes
Have you ever been guilty of making one of these five dating mistakes? 

I confess I’ve made more than a few dating mistakes. Maybe you also cringe at some of your dating memories. I’ve experienced both dating wins and losses, but I’ve been guilty of these five mistakes on more than one occasion.

1. Using a Checklist

I’ve been guilty of approaching first dates with a private checklist of qualities and requirements. But during my late 20s, I came to realize there are a lot of things that aren’t actual deal-breakers — things like being a morning person or loving the idea of running a half marathon. Previously, I had required that my potential candidate for marriage must come with pre-installed “like” and “dislike” settings that matched my own. I’ve learned to approach first dates with a much smaller checklist of deal-breakers. Now my small list includes things like personal values and character. After all, a list like that doesn’t need to be private.

 2. Getting Out Before Ever Getting In

I’ve been guilty of running off before leaving the starting line. After going on two or even three dates, the momentum starts to build and panic sets in. And then I bail before I even bought in. Just like starting a new job, the first week can be scary, but it always pays to hang in there for a little while and see how things go. You can always leave a new job that isn’t a good fit but trying to get it back after you’ve already quit is much harder. Dating can be similar, and there are times I look back on and wish I had given more time to explore a relationship a little more deeply.

3. Comparing My Relationship

I’ve been guilty of comparing. I’ve not only compared my date to other potential options, but I’ve compared the possibility of “us” to everyone else’s “us.” God may have incredible relationship plans for me, but I’ve come to realize it probably won’t look like all of the posts that fill my social media feed. Not to mention that on social media, we typically see only the best parts, not the whole picture, of a couple’s relationship. Comparison distracts us and keeps us from holding on to the best.

4. Letting Fear of Missing Out Control Me

I’ve been guilty of letting my fear of missing out control me. What if saying yes now means I miss out on an opportunity just around the corner? It’s easy for me to be so preoccupied with who might come along in the future, and this blinder blocks the present. What if there is someone funnier or better-looking just around the corner? What if I miss out? Commitment and saying yes is scary because we all fear the wrong decision, but scarier than that is making no choice at all. I’ve been guilty of that.

5. Actually Missing Out

I’ve been guilty of actually missing out. In fact, I’ve been guilty of not living my life now because I’ve been saving up certain experiences and dreams to share with my future wife — things like learning how to create my own chalk art, traveling to a dream destination and petting a lion. It’s OK to enjoy life now, and in fact it’s critical to pursue those personal, “one day I’ll pet a lion” experiences before there’s a pile of “I wish I had gone to Thailand” dreams left over. I’m no longer afraid to live my life now. I can pursue dreams now, even before a spouse.

Have you ever been guilty of making one of these five dating mistakes? 


Kevin Dietmeyer is a full-time fitness professional and serves as a pastor for students in southern Florida. He is passionate about connecting young adults with God and their individual calls to ministry. He blogs regularly at

Copyright 2018 Kevin Dietmeyer. All rights reserved. 

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