There is no denying that dating in today’s day and age is difficult, but I’m certain that people were saying the same thing in the 18th century, too! Because of my work with single moms, and the many who faced the devastation of a lost relationship, it is my greatest desire to equip single moms with effective tools to pursue a healthy relationship.

There are some that would debate that dating shouldn’t exist at all and only a formal courtship that results in marriage should exist. You have found yourself reading a dating article. So for the purpose of this piece, we’re going to assume that you are currently dating, courting, or at least contemplating it!

proud-mom-loving-teen-son-istockWe are not here to debate which group is correct.   Much can be said by both groups.  One thing is for certain — dating with kids is much more complicated than dating without.   You have other humans to think about. You have other emotions to consider.

Dating should not be taken lightly. It should be done after much prayer and consideration. So here are the top things I would tell any single mother considering entering the dating game:

  1. Only date when healthy. My goodness, I can’t tell you the number of single mothers that I have counseled that moved far too quickly from a divorce or break-up into a new relationship. It’s easy to do. Overwhelmed and exhausted with the weight of the world on your shoulders, why not find a man to fix the loneliness? Your pursuit of a new relationship won’t erase the existing hurt of an old one. It won’t heal it. Unfortunately, too many second marriages or new relationships pay the price for a broken-hearted mom who didn’t take the time to mend. Be healthy in all areas — financially, emotionally, spiritually, parentally, etc. When you are healthy, you aren’t looking for anyone to complete you. You are looking for a forever life mate, who enhances your life.

Proverbs 31: 11 “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 you are looking to “add to” someone’s life, not have them add to yours.

  1. Set boundaries early. Don’t wait to be head-over-heels for a guy before deciding what your boundaries will be. It’s too little too late. Compromise happens when preparation and planning lacks. It happens when boundaries don’t exist. And by the way, boundaries aren’t suggestions. They’re rules. They are your rules that you have determined you want to play by in your life. Pray about what you want from a relationship. Pray about what God wants. Then, outline what are the healthiest boundaries for you and your child(ren). Your boundaries may look different from someone else’s. List them out long before you decide to date again.

Check out Peace and the Single Mom: 50 Moments of Calm in the Chaos

Examples of boundaries you may consider:

  • Will I be alone with him at my home when no one is around?
  • When will I introduce him to my children?
  • What are the physical touch boundaries? kissing? hand-holding? hugging?
  • How many times per week or month will I see him? How can I ensure proper life balance, so that I don’t become obsessed?
  • Will group dating or introducing him to your friends or family first be a priority?
  1. Proceed with caution. The devastation of a divorce or failed relationship can take years to heal. The remnants that remain can have lasting effects. The worst thing that could happen to yourself or your precious kiddos is to have to go through it again. Don’t throw caution to the wind. Pray. Seek. Listen to what God is telling you. Be still before God and hear what He has for you, not what you desire for yourself. God speaks to those who listen, who have ears to hear.
  2. Don’t ignore the red flags. We all have the friend who is dating the wrong guy and everyone knows it but her! Newsflash: she knows it, too! If you embark upon a new relationship and the guy is constantly rude, late, unemployed, untrustworthy, not kid-friendly, pushing sexual boundaries, or anything else you deem inappropriate, don’t make excuses and pretend it will go away. It won’t. The thing – whatever the thing is — will only get worse as time goes on.
  3. 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” will likely leave you disappointed in the end. Again, take your time. I remember hearing a women’s pastor share about how she met her husband. They met in college and he was totally not her type. He was a “preppy” kid and she was definitely 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 to her dorm room that evening, he had sent her a dozen roses with a card that said, “Thanks for the amazing first date.” As time passed, 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 that she once had no interest in suddenly became the man of her dreams. Her heart skipped a beat as she saw him. They have been married more than 10 years now. Thank God, she didn’t let her emotions ruin God’s good thing for her life.
  4. When God speaks, respond.The Holy Spirit gives us a “gut check” when things aren’t quite right. Go with that. It is the leading and guiding of the Holy Spirit that gives you clear discernment. Don’t discount it’s significance.
  5. Choose someone who walks with the Lord. This seems like a no-brainer, but it is always surprising to me the number of women (single moms) who think they can “fix” a guy. He’s a nice guy. He’s a good guy. He’s hard-working. But…he doesn’t go to church, read the Word, pray for God’s discernment when making decisions, etc.
  6. Finding a godly man is about being a godly woman. Be wise. Don’t be in a hurry. Take your time.


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The Life of a Single Mom is a national, faith-based, nonprofit that exists to see that no single mom walks alone. To date, we have worked with more than 1,500 churches & community groups to start or improve a single mom’s support group in cities throughout the U.S. and beyond. We have a large array of books, curriculum, training materials, and online instructional videos to support ministry leaders who lead single moms. Our single mom programs focus on empowering single moms to grow spiritually, emotionally, financially, and parentally through a number of projects including: Single Mom University, Single Moms Across America, the National TLSM Single Moms Conference, and a variety of programs throughout the U.S. For more information, visit