Dating & The Single Mom: By Jennifer Maggio

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Oh, the ol’ bugaboo of dating. The excitement of a new relationship is often eclipsed by the fear that you might be left broken, hurt, and disappointed – not to mention the potential of hurting your children! This five-day devotional was written for the single mom considering dating, starting to date, or even wondering if she should begin dating in this season of life. So, let’s jump right in. 

The Life of a Single Mom

Day 1

Scripture: Proverbs 31:11

Am I healthy enough to date?

Proverbs 31:11 teaches us that a Proverbs 31 woman will greatly enrich her husband’s life. Enrich means to “add to.” It is critical we move into our dating life ready to “add to” a future spouse’s life, not simply limping through unhealthy, broken, and unhealed. How do you know when you are healthy? While not an exhaustive list, here are a few things to consider to gauge your overall health.

  • You are 100% okay with being alone. While you may have the desire to move into a healthy marriage, you trust the Lord to bring you the right partner in the right season. And even if He didn’t, you’d still trust the Lord. That’s when you know you are content in your season.
  • You don’t think about your ex. Healthy, healed people don’t rehash what an ex-partner did or said. They don’t replay the hurt. They don’t need validation by talking about it too much. A key indicator that you have healed from an old relationship is when you don’t think about him. You’re not angry, vengeful, or obsessive. If it still bothers you that he’s remarried, moved on, or breathes, you may not have fully healed from the past.
  • You aren’t looking for someone to ‘complete’ you. While a husband can certainly add value to your life, no man, however wonderful, can complete you. Christ completes us. We are whole, made well, renewed, transformed, and redeemed in Him. Proverbs 31:11 says, “Her husband can trust her, and she will greatly enrich his life.” Enrich means to add to. This means you are complete, whole, healthy, and are looking to “add to” someone’s life just as much as they enrich yours.

Being healthy in all areas is important – physically, mentally, emotionally, spiritually, financially, and parentally.

Points to Ponder:

  • Am I healthy? Should I be entertaining dating right now? What steps can I take to become healthy in all areas of my life?
Day 2

Scripture: Galatians 5:13

Compromise happens when preparation and planning lacks.

If you’ve made it to day two of our devotional time together, then you’ve likely deciphered that you are healthy and ready to start dating, but the work doesn’t end there. Boundaries are a critical part of dating, and their importance cannot be overstated. Don’t wait to be head-over-heels for a guy before deciding what your boundaries will be. Too little too late. Pray about what you want from a relationship. Pray about what God wants for you and your children. Then, outline what boundaries align with that revelation.

Step 2 to dating as a single mom: Set Boundaries Early.

Your boundaries may look different from someone else’s, but they should always align with God’s word. Boundary establishment is about seeking the Lord and following his guidance. Scripture is filled with boundary establishment – what we can and cannot do, what we should and should not do as we live a life for Christ. For example, Galatians 5:13 teaches that we have been called into freedom with Christ Jesus. He paid so that we may have a wide-open, spacious, abundant life, but our freedom is not a license to sin or satisfy our sinful nature.

Establishing boundaries early helps us guard our hearts, minds, and physical bodies against potential danger. While not an exhaustive list, here are a few examples of boundaries that other moms have established that may help you get started with a list of your own:

  • Never be alone with a dating partner in your home.
  • Don’t initially introduce him to your kids. (Hint: You may be able to casually introduce him in a social setting, such as a church event, so that your children are able to interact with him without making a formal introduction.)
  • Avoid certain levels of physical touch.
  • Assess the number of times per week or month you date versus spend time with your children to establish a healthy balance.
  • Assess his character in group settings first. How does he handle himself in a group? Is he fun? Overly competitive? Kind and respectful of others?

Points to Ponder:

  • Why is it important to establish boundaries when dating?
  • Take the time to write down the top five boundaries you want to establish in a new dating relationship.
Day 3

Scripture: Ephesians 5:15

Proceed with Caution.

The devastation of a divorce or a failed relationship can take years to heal, varying widely from individual to individual. The remnants that remain from loss and trauma can have lasting effects. The worst thing that could happen to you or your precious children is to go through it again. Don’t throw caution to the wind. Pray. Seek. Listen. Be still before God and hear what he has for you. Don’t be blinded by emotion such that you can hear the prompting of the Holy Spirit.

Step 3 to dating as a single mom: Don’t Ignore the Red Flags!

The world tells us to follow our hearts, throw caution to the wind, and jump into deep relationship waters quickly, but the Bible has much to say on wisdom. Ephesians 5:15 urges us to be careful how we choose to live. We should take care to act with wisdom, prayer, and discernment, not throwing caution to the wind, as the world would say. Scripture calls that foolish. Do not be hasty.

While there can be many red flags in a new relationship that help give us a gauge of our future with an individual, here are a few major ones to consider to guard our hearts against foolishness:

  • Is he rude, late, or disrespectful of you or others?
  • Is he unemployed? Delinquent on financial obligations or child support?
  • Does he ignore the boundaries you have shared are important to you?
  • Is he good with your children?
  • Do your family and friends like him?
  • Is he actively involved in a local church? Does he exhibit the fruit of his faith?
  • Does he have health accountability through a Bible study leader, pastor, father, or other trusted, godly role model?

If you embark upon a new relationship and observe red flags, don’t make excuses and pretend it will go away. It won’t. It will only get bigger, so be careful to proceed with caution to protect your heart and that of your family.

Points to Ponder:

  • Am I listening to what God wants for me, or am I listening to my heart? Am I approaching dating with caution?
Day 4

Scripture: Psalms 37:23

Choose someone who walks with the Lord.

This statement seems like a no-brainer, right? However, it is always surprising to me the number of single mothers who think they can “fix” a guy they are dating. They ignore the red flags. His “niceness” doesn’t replace godliness. Maybe your potential partner is a nice guy, hardworking, and kind, but if he doesn’t go to church, read the Bible, pray for God’s discernment when making decisions, and exhibit the fruit of a believer, then it is not up to you to change his heart and fix him. Only God can do that!

Step 4 to dating as a single mom: Find a godly man!

When journeying through dating, it is important to find a godly man. You want to find a man who is not just kind and hardworking but is also living according to God’s Word. Find a man who not only goes to church but reads the Word and applies it. Pray for a man who feels comfortable talking about his faith with others. If both people in the relationship are not living godly lives, one person (you) cannot carry the weight of spiritual holiness. It wasn’t God’s design for you. Be patient and wait for the Lord to put the right person in your life. It’s better to be alone than outside God’s will.

Here are a few Scriptures to consider as you are assessing his walk with the Lord:

  • Sexual morality. Run from sexual sin! No other sin so clearly affects the body as this one does. For sexual immorality is a sin against your own body.1 Corinthians 6:18, NLT
  • Work ethic. A hard worker has plenty of food, but a person who chases fantasies has no sense. Proverbs 12:11, NLT
  • Temper. A hot-tempered person starts fights; a cool-tempered person stops them. Proverbs 15:18, NLT
  • Engaged and active father. Fathers, do not provoke your children to anger by the way you treat them. Rather than bringing them up with the discipline and instruction that comes from the Lord. Ephesians 6:4, NLT
  • Exhibits fruits of the Spirit. Yes, just as you can identify a tree by its fruit, so you can identify people by their actions. Matthew 7:20, NLT

Points to Ponder:

  • Is this man a Godly man? Are you willing to wait on God to bring the right person along, even if it takes years? What are the challenges you can see with that journey? How can you overcome them?
Day 5

Scripture: Jeremiah 17:9

Let God Guide Your Heart.

Can we take a moment to acknowledge how powerful our emotions can be at times? There are moments when we can be overcome with anger, fear, sadness, and even excitement or joy. It is safe to say we have all had at least one person in our life who has given us the butterflies when they talk to us. As great as that can be, we must be careful not to allow it to overcome our discernment. We must allow God to guide our steps, even when our emotions leave us feeling giddy and excited.

Step 5 to dating as a single mom: Don’t Be Ruled By Emotions!

Jeremiah 17:9 teaches us that being ruled by our hearts can be misleading or deceitful. Jumping into the water with both feet because he gives you the “tingles” can leave you disappointed in the end. Again, as you’ll note has been a theme this week – take your time. I remember hearing a women’s pastor share about how she met her husband. They met in college, and he was not her type. He was a “preppy” kid; she was more into cowboys with a bad-boy persona. She only went out with him as a favor to a friend. Although he was nice, she found herself uninterested and waiting for the date to be over. When she arrived back in her dorm room that evening, he had sent her a dozen roses with a card that said, “Thanks for the amazing first date.”

She was instantly reminded of the kindness, gentleness, and patience he showed toward her and others that night on the date. She resolved to give it another go. She went out with him a few more times, and God slowly changed her heart as she sought the will of her Heavenly Father. The man she once had no interest in suddenly became the man of her dreams because she didn’t base her decision solely on her emotions. She sought the Lord and allowed the prompting of the Holy Spirit. They have been married for almost two decades, share four children, and pastor a thriving church. Thank God she didn’t let her emotions ruin God’s good thing for her life.

Points to Ponder:

  • Is your heart open to God’s plans for your dating life? Are you allowing yourself to be ruled by your emotions? Are you listening to what God is trying to tell you?