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Bouquet of red roses for the parent who decides to date wisely as a single mom

As a Single Mom, Decide Wisely to Date or Not Date

To date or not to date. How does the solo parent decide wisely to date as a single mom or not date?

I miss being loved and in love. Coming out of a committed relationship, finding someone who found me attractive could boost my wounded self-esteem and soothe those burning feelings of rejection. After all, wouldn’t a new romance solve the awkwardness of getting together when most folks are a couple?

Young girl writing in the sand on the shore

This period of desperately desiring love is powerfully real. Yet, jumping into the next relationship too soon can short-circuit the necessary and beneficial work of healing and becoming emotionally healthy. While dating previously meant shared activities to get to know another person, the practice has morphed into sexual encounters. Sex is wonderful in the context of a loving marriage, but to those who justify that humans can’t live without their “needs being met,” which is code for having sex, there are wholesome options.

  • DivorceCare recommends remaining single one year per every four you were in a relationship. Consider waiting to date for at least one year. Allow yourself to grow comfortable not needing another. If I’m not whole without a spouse, I won’t be whole with one. The best preparation for dating is to get healthy first and follow God’s lead. Recognize the tendency to think another relationship will be your savior. Only Jesus can be your Savior.
  • Delay remarriage. As you decide wisely to date as a single mom or not date, consider raising your child in a focused, balanced, loving single-parent home. One single mom with five children met a man she fell in love with. “I had a very different parenting style than he did,” she observed. “I felt my children had been through enough and to give them the most consistency, I dated this man until my children were grown. Then we married.”
  • One is a whole number. Though it may look different than we anticipated, living happily ever after as a single is an option.

While Single, Do It

What have you always wanted to do? Get a degree, have a career, own property, employ others, and travel? Get your pilot’s license? Scuba dive? Tour Europe? Participate in mission projects? Read the classics? Replace those serviceable curtains you’ve hated for decades? Do it.

One woman harnessed her adrenaline and tackled the neglected chores around the house to create a welcoming environment. Plenty of single women dust off neglected dreams, start businesses, go to work in their field of interest, partner with philanthropic organizations, and hone hobbies from art to gardening to sports. A neighbor opened a stylish Bed and Breakfast. Similarly, another became a family physician and organized medical trips to third world countries. “By this everyone will know that you are my disciples, if you love one another,” (John 13:35 NIV).

Develop a core circle of same sex friendships. Healthy friendships are

  • accountable
  • available
  • built on equal footing
  • interested in each other’s goals
  • often seasonal
  • able to say no and remain strong
  • honoring of confidences
  • honest with their feelings

Healthy friendships are not

  • always there
  • competitive
  • envious
  • everlasting
  • exclusive
  • rescuing
  • smothering
  • testing

Only Jesus is our forever friend. Being single can be a rich time of focused spiritual growth. While waiting for my gaping heart wound to heal, I discovered God often prefers not to eliminate the hole but artfully weaves even this into the fabric of life.

What Kind Of Friend Are You?

Consider what motivates you to be someone’s friend.

  • Do you like yourself for who God created you to be? Or are you seeking fulfillment from another?
  • Are you drawn to people because of your common pain? Or do you relate to their greatness, potential, and the opportunity to participate together in society?

When you like yourself, rejection will feel disappointing, but no longer will rejection devastate your heart or destroy your self esteem.

Accepting yourself includes

  • Accepting Jesus loves you enough to die for you
  • Being content with your age
  • Contentment with your path of good health
  • Developing your talents
  • Not self-sabotaging your potential
  • Working with your limitations and not taking on more than you are able

Get Clarity

Single or married, each of us are called by Jesus. “For we are God’s handiwork, created in Christ Jesus to do good works, which God prepared in advance for us to do,” (Ephesians 2:10 NIV). What is God calling you to do? What is he equipping you for?

Four practices help clarify God’s direction as you decide wisely to date as a single mom or not date:

  • Sleep: The first thing God blessed in Scripture was rest. “By the seventh day God had finished the work he had been doing; so on the seventh day he rested from all his work. Then God blessed the seventh day and made it holy, because on it he rested from all the work of creating that he had done,” (Genesis 2:2-3 NIV). When you are rested, life looks better and you can hear the Lord’s voice clearer. Sleep rejuvenates us.
  • Solitude: Carve out opportunities to pray. Solitude restores us.
  • Stillness: Disconnect from distractions to read Scripture and hear God’s voice. Stillness reconnects us.
  • Sabbath: “Six days do your work, but on the seventh day do not work, so that your ox and your donkey may rest, and so that the slave born in your household and the foreigner living among you may be refreshed,” (Exodus 23:12 NIV). What refreshes your spirit? One is refreshed by reading a book, while running a marathon refreshes another. As our Creator, God knows we need to refresh weekly and included this rhythm in the Ten Commandments.

Inner Wellness

To decide wisely to date as a single mom or not date, assemble a list of what character traits are important to you. If honesty is foundational to your relationships, put that at the top of your list. If financial freedom is a priority, write it down.

“Build a life worthy of inviting someone into,” said author Pam Farrel. Armed with your list of what you want in another, what work needs to be done so that person will want to share themselves with you?

Are you playing the blame game? It is “better to dwell in the wilderness, than with a contentious and angry woman,” (Proverbs 21:19 NKJV). You can be bitter and contentious or gentle, gracious, and productive.

When guilt holds you back, you can pour out your regrets and accept Christ’s unconditional love and forgiveness. False guilt that is not a result of doing wrong is a burden that serves only as an excuse, and Jesus is happy to take that away. “Take my yoke upon you and learn from me, for I am gentle and humble in heart, and you will find rest for your souls. For my yoke is easy and my burden is light,” (Matthew 11:29–30 NIV).

Whole And Healthy

Following your dreams and developing your gifts and talents, you find fulfillment in pursuing your full potential in Christ. And as a whole and healthy person, you attract whole and healthy people. Then you create relationships based not on need and dependency, but on the assurance that you are together because the foundation is solid.

  • You can simultaneously dress modestly, comfortably, and attractively. You don’t have to dress suggestively to get attention or prove you are sexy. You don’t have to prove anything to anyone. Loved by God, you are enough.
  • You have permission not to have a romantic relationship at every moment.
  • You have permission not to be anyone’s all-in-all, not to have to keep the universe functioning, and not to be anyone’s savior. “It is for freedom that Christ has set us free. Stand firm, then, and do not let yourselves be burdened again by a yoke of slavery,” says Galatians 5:1 (NIV). Secure in Jesus, you are no longer slaves to your body, singleness, or past.
  • You can run into the welcoming arms of the Lord and call, “Abba Father.”

Boaz, Not Bozo

To long for a life partner is completely normal. To have high standards and refuse to settle for second best is also completely normal. As Christ-followers, we are daughters of the King, and can expect honorable treatment from others including potential romantic interests. Men with room in their heart for a woman and her child, like Joseph of the New Testament, are noble stepfathers. When our date exercises self-control and is more concerned with our well being than with his own desires, he has the winsome characteristics of Boaz in the Bible’s chapter of Ruth.

As you decide wisely to date as a single mom or not date, always be ultra-vigilant about who you allow in contact with your child. Children can have a huge need for male approval, and these young ones don’t have the maturity to discern the difference between healthy attention and selfish motives. A parent should never have to choose between their child and a relationship. A romantic interest who loves and honors you will also love and respect your children. If your child, your horse, or your dog does not like someone, seriously consider their opinions. Horses and dogs don’t lie.

For those who will date and remarry, it is vital to know the difference between a bozo and Boaz, between toxic and healthy.

Healthy love is “patient, love is kind. It does not envy, it does not boast, it is not proud. It does not dishonor others, it is not self-seeking, it is not easily angered, it keeps no record of wrongs. Love does not delight in evil but rejoices with the truth. It always protects, always trusts, always hopes, always perseveres. Love never fails,” (I Corinthians 13:4-8 NIV).

Healthy Boundaries

A toxic relationship looks just the opposite.

Toxic is impatient and unkind, always envious and jealous. Toxic

  • boasts and is self-glorifying, arrogant and proud, self-centered and rude
  • easily gets angry and keeps track of offenses and holds a grudge
  • is thrilled when people look and feel stupid
  • loves to tell everyone about your mistakes over and over
  • runs to evil, never protects others, and easily gives up on you and others
  • motto is exploit others before they exploit you

Unlike Jesus who sacrificed himself for us, toxic sacrifices others for benefit or entertainment. Anyone who kills your hopes, dreams, and self-esteem, stealing your future, safety, or money, or destroys your reputation, peace of mind, or property is someone to remove from your circle of influence.

Tips To Decide Wisely To Date Or Not Date

If you decide wisely to date as a single mom, here are tips for the get-to-know-you process:

  • Do see each other in a variety of settings: with friends, family, co-workers.
  • Don’t only see each other when you are alone and looking your best on a date.
  • Do get to know each other for two years. The first year is the honeymoon period. The second year is often when the masks go down, revealing a more genuine person.
  • Don’t pretend you are someone you are not. If you don’t really enjoy the hobbies that he does but enjoy being with him, be honest.
  • Do ask trusted family and friends what they see in this person.
  • Don’t ignore concerns of trusted family and friends. Nor should you make your decision solely based on their advice.
  • Do measure your relationship by how much each of you grow in your relationship with God
  • Don’t give up dreams, interests, and relationships with friends and family to be completely devoted to your romantic interest.
  • Do remember no one is perfect but never tolerate poor or disrespectful behavior.

These Red Flags Should Send You Running

While getting to know another person, be aware of behaviors that foreshadow

  • Feeling like you have to choose between your child and your date
  • Anger
  • Smothering
  • Focus on the physical aspect of the relationship
  • Addictive behaviors (alcohol, computers, drugs, girl watching, movies, pornography, television, spending—anything that controls and takes the place of God in his life)
  • Disrespectful to his mother, sisters, waitress, and other women
  • Uncomfortable making eye contact
  • Secretive
  • Manipulative
  • Disrespectful of your boundaries. One friend said she felt disrespected when her date pushed past her to tour every room in her home.
  • Bulldozes through your “no”
  • Unhappy
  • Negative and critical
  • Places responsibility for his emotions on others (“You made me . . .”)
  • Unable to remember blocks of his childhood. This can be a survival response to abuse. Trained professionals can help heal a hurtful past so unwholesome behavior does not affect family members.

Friends First

Dating is about first becoming friends while minding your values. For you and your child, avoid the appearance of scandal. No date should be asking or pressuring for sex. Respect, honor, and integrity are the foundation for love. But without respect, honor, and integrity, there is nothing but toxicity and control. A relationship that is not respectful and loving without sex, certainly won’t be with sex. A friend confided, “This man wrote me beautiful letters every day. When we went out, we had sex. I thought it would be fun, but I haven’t heard from him since.”

Solid relationships consist of two healthy people and one well-communicated commitment level. Both parties know the level of their relationship, and expressions of affection, gifts, and interactions match what is appropriate at that level.

Emotional lines can get blurry in friendship, work, and dating relationships. At what point do you trust someone with personal information? When or why would a person loan money or ask for a loan? When would a person comment on another’s clothes or behavior? Who do you allow access to your social media?

Play It S.A.F.E

These signposts help set safeguards when sharing yourself with others. To decide wisely to date as a single mom or not date includes knowing how to play it SAFE:

Share incrementally

Always have an escape hatch

Find the forward movement

Evaluate favors carefully

Share incrementally. Let relationships evolve as you build a foundation of trust. Do not give personal information when you first meet. Answer “Where do you live?” with the city or area, not the street. Find the link between your friendship circles before you allow access to your social media. Look for safe ways to develop a relationship through participating in the same Bible studies, charity events, volunteer activities, or hobbies with groups of people, then slowly evolve into smaller social circles such as a dinner party or group date with friends. Evaluate your comfort level on a double date before a solo dating experience.

Always have an escape hatch. Let someone know where you will be, who you will be with, and when to expect your return. Trust your intuition, and even if you never know why you felt uncomfortable, obey those nudgings from the Holy Spirit. Drive to and from your dates until you thoroughly check out a person and feel safe.

  • What is their online presence?
  • What are they writing on social media?
  • Who are their friends and what do they talk about?
  • Check watch lists to see if their name appears.

Consider Their Circle

Who we keep company with says a lot about a person. What connections, community, and influences will interact with you and eventually your child? Are there common connections who can share their experience with this person?

What are their work relationships?

    • Do you know anyone from the company where they work?
    • What is their employment history?

Who is their social circle?

    • Are they close to family? Have you met any family members?
    • Are you comfortable with their friends?
    • Where do they spend their off-work time?
    • Do they have friends they do not want you to meet?

What is their financial status?

    • Are they living within their means or stressed by debt?
    • Are school loans repaid?
    • Do they use credit more than you feel comfortable with?

How do they handle responsibility?

    • What is his attitude toward his job and employer?
    • Do they abuse or frequently use alcohol, drugs, or tobacco?
    • How clean is their car? Later, how clean is their home, patio, or yard?
    • Do they have good personal hygiene?

Find Forward Movement

Many women express frustration over male friends they cooked, cleaned house, or did laundry for, yet he didn’t see her as dating material. Resist the impulse to do the tasks of a spouse when that is not your role in the relationship. Be cautious if you mostly give while another mostly takes. Give when your time, talent, or treasure is freely offered without strings. To date wisely as a single mom, do not give when you hope your actions will buy the heart of another. Clearly communicate agreements if you want the commitment level of the relationship to be clear.

Evaluate favors carefully. When it comes to income, singles grasp the harsh reality, “I am on my own.” Depending on someone else’s money to pay our way in life isn’t emotionally healthy. Repayment of some kind is always required.

Favors can turn quickly into obligation without you knowing the rules changed. This principle extends to gifts you accept from your date’s friends and family. A high-ticket item may come with pressure to move your relationship to a higher commitment level than you desire. You can feel obligated to date someone because everyone in that circle has been nice. Be careful when accepting gifts that could leverage you right into the family. Every favor, gift, minute you spend with someone forges an emotional bond, so the more serious the relationship becomes, the harder to walk away without causing pain to them or you.

Remarriage

Marriage is glorious and challenging. Step-families have the added dynamics of ex-spouses, visitation rules, court orders, and complicated holiday schedules. Law offices receive the most phone calls during holidays when ex-spouses battle over who has the children. Statistics indicate 70 percent of second marriages with children end in divorce, causing a second major loss of family structure for tender hearts.

And 30 percent of stepfamilies succeed. If you decide to remarry, strengthen the foundation with resources, mentors, and supportive community. Situations vary significantly. Some estranged parents remain strong in their parenting roles. Others disappear. Some chaotically come and go. However,  stepparent will not replace a parent, but a quality adult can be a beneficial, loving, and nurturing addition to the life of a child. “One of our children is hers, one is mine, one is adopted, and one is ours,” a stepdad said. “But I can’t remember which is which.” In their blended family, the only thing that matters is that they belong together.

Are You Relationship Ready? 

To decide wisely to date as a single mom or not date, consider if you ready for a relationship leading to marriage? Here is a quick checklist:

  • Have you been on your own? Are you paying for your own housing, food, personal items, car, phone, and insurance? Are you responsible for personal decisions, schedule, and life plan? Are you confident you and your child could be fine as a team without a spouse?
  • Are you debt free or working a consistent plan to be financially responsible?
  • Do you have a strong plan and direction for your life? Can you follow God’s leading for you and your child?
  • Do you have a pattern of success in your work? Or a clear path to college or grad school, and career?
  • Do you have a dependable, authentic group of friends you can confide in and trust their counsel?
  • Do you have a healthy relationship with your parents, grandparents, and extended family—or sought to establish health from your side of the relationship?
  • Have you dealt with your family-of-origin issues? Have you pursued counseling or mentoring to overcome hurt caused by a parent’s addiction, abandonment, or abuse?
  • Have you acknowledged and forgiven hurts from past relationships?
  • Have you established boundaries to protect your child and your own heart?
  • Have you dealt with your addictions involving drugs, drinking, pornography, sexual promiscuity, gambling, shopping, or eating?
  • Have you closed the gate in a healthy way on romantic partners? Are you able to end a relationship in a positive manner?
  • Is your divorce final? Has a custody settlement been agreed? Have you divided property?
  • Have you given yourself time to regroup and adjust to life as a solo person?
  • Is your child ready to have a new person enter your life? Children are notas resilient as you might want. Before you expose your child to your romantic relationships, consult a licensed counselor who specializes in children.
  • Have you taken an honest look at both sides, yours and your ex’s, of what went wrong with your relationship? Have you gained skills to correct past mistakes and establish a strong and healthy life for you and your child?

Reflection as You Decide Wisely To Date or Not Date

Any questions left unchecked are the areas you want to take care of before jumping into a serious dating relationship, engagement, or marriage. (For more on living healthy as a single with healthy relationships, see Bill and Pam Farrel’s Single Men Are Like Waffles, Single Women Are Like Spaghetti.) When a relationship is growing serious, and you believe you may be headed for marriage, consider working through together with the man you are dating, The Before You Marry Book of Questions. When we are healthy, we are fearless of self-assessment and self-improvement so we can be our best for those we love, including the one we will marry.

For You

As you decide wisely to date as a single mom or not date, consider living life as a single person for at least one year. Learn to interact authentically with others, attend events, and enjoy.

Find more resources or the solo mom’s success in The Ten Best Decisions A Single Mom Can Make: A Biblical Guide for Navigating Family Life On Your Own by Pam Farrel and PeggySue Wells.

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Meet PeggySue

When I’m not writing, I parasail, scuba dive, skydive, snorkel, and haven taken (but not passed) pilot training. My greatest adventure has been being called Mama by seven awesome children and Mimi! by my Grammy awards.

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“Opposite words and conflicting desires clash in this action-packed, page-turning suspense.” -Richard Paul Evans, #1 New York Times Bestselling Author of 45 books including The Christmas Box.