Dating for two is difficult; dating in a crowd is downright complicated. The kids are engaged, at least on some level, even when you don’t think they are. And everyone has strong emotions and opinions about who is involved and what the outcome might be. In other words, the whole family is dating. Table for 20!

This article shares with you a number of dating best practices for single parents and the singles who date them.

Introductions and Early Dating

Early on your kids may meet your date and be intrigued to learn a little about them, but the first few dates should primarily be about the two of you. At first reference your date as “a friend” or if your kids are prepared, call them your “date.” Casual introductions are fine when you start dating someone, but don’t proactively put your kids and the person together until you are pretty sure there are real possibilities for the relationship. This is especially true for children under the age of five who can bond to someone you are dating more quickly than you can.

As your interest in the person grows, gradually become more intentional about finding time for your boyfriend and kids to get together. Tread lightly at first and continue to monitor and process everyone’s fear or concerns. If he has children as well, it might be wise to orchestrate early get-togethers with just one set of children. You might, for example, engage in an activity with your dating partner and his children one weekend and then have him join you and your kids the next. Navigating multiple new relationships can be overwhelming. Breaking the two families into parts can be helpful initially. Eventually, though, assuming your dating relationship continues to deepen, you’ll want to get everyone together for a shared activity.

Avoid a Quick Turn-around

Parents who begin dating quickly after the end of a relationship (whether by death or divorce) or who reach a quick decision to marry after a brief dating period often find their children more resistant to the marriage. This sabotages the ability of a stepparent and stepchild to get off on the right foot with one another and puts the family at risk.

Healthy dating begins with self-examination

Smart moms take a good long look in the mirror before dating. They examine their motivations for dating, fears, loneliness, and unresolved hurt (e.g., after divorce). How do you know when you’re ready to date? When you don’t need to.

Engage in “What if?” Conversations

Even before dating, single parents begin a series of conversations with their children that wonder, “What if I began dating? How would you feel?” Periodically, they engage the conversation again and again: “What if John and I began dating regularly?” “What if John’s kids came over every Friday through the summer?” “What if he and I were to get engaged?” Each dialogue is both assessment (i.e., how are my kids feeling about these possibilities and realities) and intervention as it prepares them for what might happen. A smart single mom doesn’t let her children’s emotions dictate her dating progress, but she does listen and give serious consideration to how the children are feeling (becoming a couple is up to you; whether you become a family is up to them). Engage in these conversations throughout your dating experience, especially in anticipation of each stage of a developing relationship.

Manage Sexual Pressure in Your Relationship

Sexual temptation is ever present in dating relationships. You must have a plan for managing them (Read Colossians 3:1-11). And do not cohabit. The sexual disobedience hamstrings your ability to disciple your children; plus, research tells us the most dangerous place for a child today is in a cohabiting stepfamily. You can’t get around it; there’s nothing wise about cohabitation.

Learn All You Can About Stepfamily Living

Nearly twenty years of counseling, coaching, and training blended families has revealed to me this secret of successful blended family couples: They work harder at getting smarter about stepfamily living. Getting smarter means learning all you can about how stepfamilies function, operate best, and why they have the unique complexities that they do. You may know how to drive a car, but driving in snow and icy conditions requires a different knowledge and skill set. Nearly all blended families have inclement weather to manage as they drive (especially in the first few years), so adopt the attitude of a learner.

Adapted from the book Dating and the Single Parent by Ron L. Deal. Used with permission. All rights reserved.


ron dealRon L. Deal is president of Smart Stepfamilies™, director of FamilyLife Blended™, a popular conference speaker, and author/coauthor of a series of DVD’s, books, and curriculum for stepfamilies including The Smart Stepfamily, The Smart Stepmom, The Smart Stepdad, Dating and the Single Parent, and the book The Smart Stepfamily Marriage. His one-minute radio feature FamilyLife Blended can be heard daily on stations nationwide and online. Tune in to his weekly Periscope broadcast (follow “Ron Deal”) on marriage and blended families. Learn more at


The Life of a Single Mom logoThe 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