Singles

How to Return to Dating After Taking a Break

Are you re-entering the dating world after a season away? Here’s how to walk forward with wisdom and a deep trust in God’s timing so you don’t lose yourself in the process.
Jul 17, 2025
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How to Return to Dating After Taking a Break

Are you ready to begin dating again? Perhaps you have found yourself in a position that you haven’t been in for quite some time, entering back into the dating pool. It can be intimidating, whether this is because you recently exited a long-term relationship, have taken a step back from dating to focus on other priorities, or are ready to get serious about finding a partner. Preparing your heart and mind ahead of time can help set you up for success.

Watch the Patterns

Pattern recognition can prove a beneficial asset when it comes to entering the dating world again. This is not limited only to hazardous patterns that are “red flags” but also to identifying healthy patterns of “green flags.” Take an assessment of the qualities you possess that are especially unique or an asset. Perhaps you are a good communicator, or you have a pattern of conscious fidelity. Consider where these qualities have produced fruit in relationships, romantic or not, and watch for the times they have been misused or taken advantage of. After identifying your own past patterns, consider tendencies where you can improve. Remember that unhealthy or toxic habits on the other person’s side also exist, so taking the same account for the red flag patterns you tend to attract will help you to watch for them in an early stage of getting to know someone. Pattern recognition is not to condemn you or others, but to help you see what you are doing well, what others are doing well, and where improvements can be implemented to benefit all in the long run. Highlighting patterns can also help you to pray effectively for the Lord to move within your own self so that you may be refined to be a better future spouse.

Be Yourself

A temptation exists when it comes to dating to create a facade that you are just about the closest thing to a perfect person a human can become. This temptation can lead us to please people, hide aspects of our lives that are not easy, and sometimes even mirror back to the other person what we perceive they desire in a romantic partner. It can only last for so long before you will find yourself exhausted from keeping up a false appearance, and the other person loses out because they are not given the opportunity to know the “real you.” A great opportunity is also lost in that you are closing the door for the potential to be known for who you really are. Make the choice not to forfeit the glorious potential for someone to know the real, authentic, genuine you by vulnerably bringing your true self to the table. This may reveal that the match is incorrect or offer you a connection unlike anything you have ever known.

Know Your Worth

Even if in the past you have experienced situations where others have not known your worth, that does not determine your future relationships. Consider how a water bottle can be fifty cents at a grocery store or five dollars at an airport, without changing a single aspect of that item. In the same way, someone may have hurt you by taking you for granted, demeaning you, or not recognizing what a gift you really are, but that does not need to be the end of the story. Do not let your worth depend on a gauge set by man; let God be the One who determines your worth. When you use His measurements, you find that you are loved, sought-after, and chosen. Know your worth and settle for nothing less than a spouse who sees you as a son or daughter of God and offers you the respect that comes from being a Royal Child of the King.

Pray for Discernment

Asking for discernment is one of the greatest prayers you can pray in all things, especially when it comes to relationships. God sees what we do not, for He knows the hidden truths of the heart. 1 Samuel 16:7b reminds us: “The Lord doesn’t see things the way you see them. People judge by outward appearance, but the Lord looks at the heart.”

When considering if you should pursue a dating relationship with someone, ask the Lord to reveal that person’s true heart to you. Sit before Him and ask for the discernment to know if you should move forward, kindly decline getting to know them, or be shown by example the truth of the other person’s character. This can save you time, heartache, and it will also help grow your trust and dependance on God. It is wise to ask Him to make it clear with the holy peace only He can offer, for steps to take onward. With such a prayer, you must also surrender the itch to control the outcome or assume you know better than He does. He truly knows what is ultimately best for you and the other person. A prayer for discernment invites you to listen for His opinion on your life above your own.

Let God Author

The best thing you can do when “putting yourself back out there” is to allow God to Author your love story. Patience is a virtue, but it is also more about trust than the span of time. This trust is one where you allow God to lead you forward in His timing, ways, and ultimate Will for your life. God has good things for you, and He has your best in mind even more than you do believe it or not. When we surrender the pen to Him, we see that He can open doors you never knew existed, bring about healing you never knew possible, and redeem the lost years you thought were wasted. Joel 2:25b shares, “I will restore to you the years that the swarming locust has eaten.”

This means that God can redeem what you counted as squandered if you allow Him to do so. When you allow God to author your story, you relinquish control, surrender your will, and find that He really is the greatest Romantic of us all. God’s authorship over your life is more than just a romantic partner—it is the story of a sinner who is deeply adored by his or her Creator. Your story is irreplaceable in the grand story of the Kingdom of God here on earth. Allow Him to bring about more than you could ask for or imagine.

Getting back into the dating pool after a time away can offer a lot of unknowns that stir anxiety within, but you do not need to be afraid. Partner with the Lord and ask Him to help you grow as a person during this time and come to know Him better than you ever have before. Remember that the greatest relationship you will ever be offered is that of one with the Lord, and He is good and can be trusted. Rest that He is worthy to be trusted with how He leads you forward, move forward with joyful anticipation.

Related Resource: Need a Laugh? Listen to Talk about That!

Two quirky and cerebral creatives talk it out! As writer and former History teacher, John Driver, goes toe-to-toe with his best friend and comedian, Jonnie W., in hilariously real and genuinely insightful conversations about life, history, current culture, faith, and everything in between. In this episode, John goes for a jog and gets attacked by an unlikely predator. Meanwhile, Jonnie decides not to tell his Kenny Rogers joke for a very good reason, and dreams of getting a key to the City (any city will do). Plus, we learn why anxiety is like a rocking chair (and not in a good way), and how security can become an unhealthy fixation. If you laughed out loud listening to this episode, be sure to subscribe to Talk About That on Apple and Spotify!

Photo credit: ©Getty Images/Minerva Studio

Cally Logan biography author photoCally Logan is the author of three books, including The Wallflower that Bloomed, winner of the 2025 Reader’s Choice Christian Literary Award and the Henri Award, and an Expert Writer for Crosswalk.com and The Rooted Truth. Her heart finds beauty in the mysteries of life and in the glory all around us in the details, big and small. Storytelling is her passion, and she believes each and every one of us holds a unique, valuable, and hand-written story by God, and together, we are part of the Grand Story He has written. She received her B.A. Degree from Regent University and has taught US History and Western Civilization for nearly a decade. Her works have been featured on outlets such as Jesus Calling, The 700 Club Interactive, Propel Women, and many more. In her spare time, she enjoys spending time in nature, watching movies, and woodworking. Check out her website, callylogan.com, or find her on Instagram @CallyLogan.

Originally published July 21, 2025.

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