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Moving On: How Do I Know I'm Ready?

Moving On: How Do I Know I'm Ready?

EDITOR'S NOTE: He Said-She Said is a biweekly advice column for singles featuring a question from a reader with responses from a male and female point of view. If you've got a question about anything related to singleness or living the single life, please submit it to He Said-She Said (selected questions will be posted anonymously).

QUESTION: How do I (as a new Christian) start dating again after a failed engagement and loss of an unwed pregnancy and how do I know if I’m ready?


Any relationship dissolution is tough, let alone an engagement.  Add the loss of a child into the mix and your situation becomes especially disconcerting.  By asking this question, you are undoubtedly aware of the emotional challenges you face and the difficulty of re-entering the dating forum after having thought those days were over.

Many friends and well-meaning individuals will probably be offering up a number of explanations for and speculation why this may have happened.  Although this can supply some comfort, you may want to reach out to a professional counselor in order to properly handle all of your emotions and stages of grief.

From a lay standpoint (and a former fiancé myself), I highly suggest you do abstain from dating until you are completely ready in order to refrain from leading (or misleading) a potential suitor (or yourself) into a relationship you’re not prepared for.

Some of the indicators you can look for which may signal you are nearing that time to date would be when you no longer feel remorse for the break-up, you have no anger or bitterness towards your ex-fiancé, you begin to make new memories in places you frequented together, you speak positively about your past relationship, when you see spiritual fruit from opportunities which wouldn’t have been possible had you married, and you begin to enjoy the present and look forward to the future (including getting pregnant again) rather than dwelling on the past.

There are some who never seem to “move-on” from their past hurts and ill feelings, and end up carrying them from day to day and relationship to relationship.  Years and even decades later, we hear how someone did something which has caused them to be where they are today.

Don’t allow yourself to be embittered because of your past hurt.  Develop into the person God wants you to be.

You will know you are ready to date when you see your broken engagement as an opportunity that has allowed each of you to pursue, grow and serve in many more ways than you could have had you been married.  

Start slow, go out in groups or with friends, and allow a new relationship to develop.


Let me first tell you how proud I am that you see the importance of doing things different. Because you ARE a new creation; you have the power given to you by the Holy Spirit to live a different life. You do not have to fear the next step because God is already there, preparing the way. 

This is the one about whom it is written: “‘I will send my messenger ahead of you, who will prepare your way before you" (Matthew 11:10).

So, are you ready to date again? Are you ready to make a new commitment to someone? I do not know how long it’s been since all these things happened to you. For me, I would want to make sure I have begun the healing process. Have you thought about getting some Christian counseling? Have you talked with your pastor or another leader your trust? Do you have a support group of friends in place that can be praying for you as you make this new start?

If and when you meet that new guy in your life you will want to share some of your past. I would encourage you to pray about what to share and when.  There are no guarantees anyone can accept all of your past and/or mistakes.  This is simply the result of our sin. However, because we all have sinned and fall short of the glory of God, we are assured that none of us deserves anything, but Christ died to give us everything. A man who says he loves the Lord should love you, mistakes and all.

Final thoughts: take it slow, building meaningful same sex friendships, then opposite sex friendships. Pray and ask God for His timetable, to let you know when you have healed enough to date again. Then step out in trust.

My steps have held to your paths; my feet have not slipped (Psalms 17:5).

HE is … Cliff Young, a contributing writer and a veteran single of many decades. He has traveled the world in search of fresh experiences, serving opportunities, and the perfect woman (for him) and has found that his investments in God, career and youth ministry have paid off in priceless dividends.

SHE is … Kris Swiatocho, the President and Director of Ministries and Ministries. Kris has served in ministry in various capacities for the last 25 years. An accomplished trainer and mentor, Kris has a heart to reach and grow leaders so they will in turn reach and grow others. She is the author of three books: Singles and Relationships: A 31-Day Experiment (co-authored with Dick Purnell of Single Life Resources); From the Manger to the Cross: The Women in Jesus' Life; and the most recent, Jesus, Single Like Me with Study Questions (includes a leader's guide and conference/retreat of the same name).

DISCLAIMER: We are not trained psychologists or licensed professionals. We're just average folk who understand what it's like to live the solo life in the twenty-first century. We believe that the Bible is our go-to guide for answers to all of life's questions, and it's where we'll go for guidance when responding to your questions. Also, it's important to note that we write our answers separately (we think they sound eerily similar sometimes, too!). 

GOT A QUESTION? If you've got a question about anything related to singleness or living the single life, please submit it to He Said-She Said (selected questions will be posted anonymously). While we are unable to answer every inquiry, we do hope that this column will be an encouragement to you. Click here to visit the He Said-She Said archives.

Publication date: October 25, 2012