Best Practices for Dating Single Parents (and the Singles Who Date Them)

Ron L. Deal

Our whole family is dating this guy. -Rachel, 22 years old

Sometimes kids say it best. When asked what she wishes her mom would do differently while dating, Rachel, a smart young graduate student, replied, “I wish she would recognize her own impulsivity and emotional rollercoaster. She does and says things without recognizing that to some extent our whole family is dating this guy. This year I came home four times from college and he was in town every single time. After I went back to campus each time mom said, ‘I never get to see you!’ Yes, well, that’s because you were with your boy.”

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!

My newest book, Dating and the Single Parent, examines the complex process of finding love in the midst of a crowd and includes a number of dating best practices for single parents and the singles who date them. Here are just a few:

Realize that You’re not just Forming a Relationship, You’re Creating a Family

When kids predate dating, the couple’s relationship inherently creates competing attachments. The choice to be with the dating partner or children generally means the other is left waiting…and wondering how their relationship with you is being influenced by your relationship with the other. In addition, children commonly feel some insecurity by mom or dad’s relationship with another person. Wise singles recognize this important dynamic and don’t assume that becoming a couple necessarily means that they can become a family. They attend to both and take time assessing how the potential stepfamily relationships are developing.

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 singles take a good long look in the mirror before dating. They examine their motivations for dating, fears (e.g., their children not having a father), 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 Sara and I began dating regularly?” “What if John’s kids came over every Friday through the summer?” “What if she and I were to get engaged?” Each dialogue is both assessment (how are my kids feeling about these possibilities and realities) and intervention as it prepares them for what might happen. A smart single parent doesn’t let their children’s emotions dictate their dating progress, but they do 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.

Offer Soft Invitations to Older Children

Teens and adult children need to move toward your dating partner at their own pace. If you make it your agenda to get them to accept your partner and relationship, you may be shooting yourself in the foot. Instead, make opportunities for them to get to know each other, but don’t force it. Soft invitations such as, “Roger will be having dinner with me on Saturday. You are welcome to join us if you’d like.” show respect and allow relationships to develop at their own pace.

Acknowledge and Label Child Fears

Children of all ages, young to old, benefit when a parent says, “I can see that the idea of my dating scares you. You are missing mom/our family/etc. and probably don’t want any more changes to our family. I get it. I appreciate your being honest with me.” Use phrases like “this scares you,” “you’re afraid that our family won’t be the same,” or “you don’t want to have to change schools or leave your friends.” This type of response validates the child’s fears. It also shows them their feelings are important to you, keeps the communication door open, and helps children put labels on their own emotions (which is very important for young children especially).

Pace and Balance Your Dating

If you fall in love don’t abandon your kids by spending all of your free time with your newfound love. It’s tempting, but doing so taps your child’s fears that they are losing you and gives the false impression to your dating partner that you are totally available to them. You’re not. Don’t lose your balance.

If You Don’t Have Kids

Do your relationship a favor, encourage the single parent you are dating to “go home” and be with their kids, without you, every once in a while. This has two benefits: (1) it helps lessen the fears of the children; and (2) it keeps perspective in your relationship. Might you feel a little left out and lonely? You bet. But then this relationship is as much about them as it is about you. Having said that, let me be candid: if you can’t get used to this notion and learn how to deal with it, then you’ll be a lousy, miserable stepparent.

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 boy/girlfriend and kids to get together. Tread lightly at first and continue to monitor and process everyone’s fear or concerns. If the other person 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 partner and their children one weekend and then have your partner 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.

Expect Hot/Cold Reactions

Liking a parent’s dating partner sometimes creates a loyalty problem for kids: They don’t know how to embrace everyone and not hurt feelings (especially the other biological parent). Because they are caught in a loyalty conflict, children sometimes warm up nicely to a dating partner and then turn cold. Sometimes they vacillate back and forth. Don’t panic or judge the children too harshly. Confusion comes with the territory. Relax and work with what they give you.

Articulate Your Silhouette

Since you can’t judge lasting love by physical accoutrements or initial biochemical attractions, you need an objective measure of the qualities, attributes, and character of the person you are looking for. But you also need—and here’s where single parents fall short—a silhouette of the type of family you are hoping to create. If the person you are dating isn’t good parent material (with yours or theirs), for example, you ought to move on. Yes, not liking the fit between the person you are dating and your kids is a deal breaker, even if you love them as a partner.

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.

Pick up a copy of Dating and the Single Parent ( Amazon or Barnes & Noble) for yourself or someone you know to learn more dating best practices including how to manage your fears and those of your children, what online match-making sites will never tell you about dating and kids, and recognizing flashing yellow lights, red stop lights, and green “keep moving forward” lights. Plus, you’ll learn how to deepen a good relationship that is moving toward marriage while attending to the children and their needs, how to make the engagement announcement, and six steps you can take to prepare for blended family living after the wedding.