Top 5 Dating Mistakes You Don’t Want To Make

In Advice and Encouragement, Dating, For the Guys, For the Ladies, Relationships, Single by Debra Fileta18 Comments

What do you think were the top relationship mistakes my readers reported making?

Think about that question for a moment. Maybe even ask yourself what YOUR biggest relationship mistake has been?

At the beginning of each year, I pose this important question to my blog readers for a chance to reflect on the relationship mistakes of the past, and set goals for the future.

Here’s a countdown to the TOP 5 relationship mistakes reported from the least reported to the greatest:

#5: Having Sex Prematurely

#4: Settling for a Wrong Relationship

#3: Not Having Enough Boundaries

#2: Staying in a One-Sided Relationship

#1: Not Taking A Risk to Start One

Wait a second. What?!? Did you catch the #1 mistake? Not toxic relationships. Not too many relationships….


It’s true! More than ⅓ of readers polled explained that the BIGGEST mistake they made in dating was actually not taking enough risks to start a relationship. Sitting on the sidelines and letting life happen.

I wonder how many of you can relate? I know I can. As I look back at my “pre-marriage” years I realized that for so long, I spent many of my years as a single woman living out of FEAR than out of FAITH.

I was scared of making mistakes. Scared of disappointing others. Scared of failing. Scared of making the wrong choices. I had gone through a season of singleness after a breakup, where God brought so much healing into my life.  I felt ready to try dating again. But even then, I was still afraid to put myself out there. Still afraid of making the wrong choices. Still afraid of the possibility of rejection.

And for so long I let the fears of my life paralyze me from living my life.

Oftentimes in life, it’s so much easier to make choices when it comes to career, church, ministry, or friendship. We call it “faith” as we sit around waiting for a relationship to happen, but sometimes we need to come to terms with the reality that it’s really just fear that’s preventing us from moving forward. 

But what is it about love and relationships that seems to paralyze us? What are we so afraid of? Maybe when it comes to love and relationships, we feel that we’re on our own. We wonder if God is there, or if He even cares. We feel left without direction, and sometimes, even without hope.

No matter who you are or what relationship mistakes you’ve made in your past, I truly believe that God is longing to give us the wisdom, the courage, and the faith to step into healthy lives, and in turn, healthy relationships.

I believe with all my heart that God has given us everything we need to know in order to do relationships WELL.

As a Professional Counselor specializing in Relationships, I get thousands of emails from people seeking relationship help from relationships gone wrong, or relationships gone “no where at all”. Though I desperately wish I had the ability to sit down for coffee with each and every single one of you, the reality is that it would take me THOUSANDS of hours to meet with and counsel each and every individual that comes my way.

But with all the questions I’ve received swirling around in my mind and heart, I decided to pour my heart, education, and experience into a 21-Day Program that I believe has the power to change hearts, lives, and relationships.

It’s 21-Days filled with the most strategic lessons and practical relationship advice that I’ve found to be effective as I’ve worked with client after client, pouring hours of research and study into this important topic. In addition to all of this, it includes a private Facebook Group where myself and hundreds of other singles who have gone through/are going through the 21 Days to Jump Start Your Love Life Program get to interact, discuss, and encourage each other. It’s important to encourage each other along the way!!

Maybe it’s time to let go of your fears, in exchange for faith.

I hope you’re ready. Click the photo below to find out more and sign up for yourself: 

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Debra Fileta is a Professional Counselor, national speaker, relationship expert, and author of True Love Dates: Your Indispensable Guide to Finding the Love of Your Life, where she writes candidly about dating, relationships, and how to find true love. Her newest relationship book is set to be released in the Summer of 2018! You may also recognize her voice from her 200+ articles at Relevant Magazine,, and all over the web! She’s also the creator of this True Love Dates Blog!  Connect with her on Facebook or Twitter or book a session with her today!


  1. My, how those words rang so true for me! I can’t wait for this 21 Days to come out… I’ve taken a couple risks wayyy out of my comfort zone recently, but my struggle is definitely the follow up AFTER even that! I’ve been truly blessed though, by your words, and a Father who knows what’s in store for me. I wouldn’t be at this level of comfort and confidence without either! Thank you for touching on this… I needed the reminder to go out and take risks, and not be afraid 🙂

    1. Author

      So good to hear, Courtney!!! I love this story 🙂 Thanks for your kind words…may God continue leading you into “godly risks”….you go, girl!

  2. This is wonderful! I mean, not wonderful that so many of us are living in fear. But wonderful to know that we’re not alone in our fears. That they’re relatable and real. Thanks Debra, for following the Lord and pouring your life into speaking about healthy relationships! It’s refreshing and motivating to slowly come out of the mentality that as a woman, it’s ALWAYS best to wait and never appropriate to take a risk. And I’m realizing now that I was in a way taking refuge in that because I was afraid of being vulnerable. Anyway, I’ve read a lot of your articles and your book and I wanted to say thank you! Praying God continues to use you in impactful and meaningful ways. 🙂

    1. Author

      This is amazing to hear, Karen!!! Thank you so much. I’m so encouraged to hear how God is using this ministry in your life. What amazing lessons He’s teaching you. Great things are ahead for you, my friend!!!

  3. I am sooooo excited for this program! Finally at a place where I can afford it and your book so I am expecting great things to happen in my life with His help and guidance and yours! I thank God for bringing you into my life!

    1. Author

      I love your excitement, Ruthie!!! And I’m so happy God has blessed you with the resources that you need to enrich your life in these ways. God is so faithful through both times of plenty, and times of need. Thank you for your sweet words, they mean more to me than you could ever know. I’m so glad God brought you here.

  4. SO thankful to have been part of the pilot team for this program. All I can say is, get ready, because you guys are going to LOVE this program! It’s so good! You will grow in Christ and grow as a person. DO the program! You won’t regret it!

  5. Hi Debra. I can’t describe how grateful I’m for the works and the time you put into being a blessing to us girls, who’ve made mistakes and are getting our confidence back on. God bless you. I agree totally with the relationship mistakes. Reading this make me know I’ve evolved out of the pitfalls I found myself in but now so fearful on moving ahead even with the guiding eye of a loving heavenly Father, I’m still scared of making wrong choices, of losing myself again, and funny, of sharing of my time and relationship with God with someone else. Also, how does the 21days work. Online class
    class? I’m in Nigeria, Africa.

  6. I havent been on Date for 19 years. My pastor in my first Church was treated badly and made us all frighted of relationships not a nice feeling.

  7. I have high-functioning autism, and I’m very shy and introverted. I’d like to be in a relationship but I don’t think I have what it takes to start one much less keep one.

  8. Blessings Mama for the good work you are doing . And l bless God who after years of waiting, has finally blessed me with a good relationship which will end in marriage soon! More of the good work Mama.

  9. Oh my, thank you so much Debra for these powerful yet encouraging and lifting our spirits up to not be afraid of risk and get out of our ”fear comfort zone”. And to actually get out there and Just have Faith….. Can’t wait for 21days, super excited about it….

    1. Author

      I hope you enjoy the program, Carol!! Thanks so much for the kind words and keep me posted as you go through it!

  10. Hi, Debra! I’m a little late to the party here, but I’ve been reading through (and enjoying) TLD, while at the same time wondering how best to reconcile your idea of dating upward (especially the triangle theory) with the problem this article addresses: relational passivity.

    Let me explain. When someone’s life focus is to find a significant other, I think it’s safe to say that they risk idolizing relationships — at the expense of their walk with God.

    But can’t the opposite path lead to fallacy as well? Is it possible to be so caught up in trying to live your life for ministry — and for your walk with God — that you do so to the detriment of possible relationships?

    In your book, you criticized a portion of your single years for having beeen spent ‘hunting for a man,’ instead of focusing on God. But in the article above, you also challange Christians everywhere to stop being so passive in starting relationships.

    I’m sure I’m overthinking this, but I’m confused all the same. Assuming relationships don’t just happen without our own direct involvement — while also remembering that God must be the great, overarching focus of our lives — where do you draw the line between ‘spouse hunting’ and responsible searching for relationships? Or between living for God and romantic passivity?

    Thanks for any more light you can share on the subject!

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