11 Best Practices for Dating as a Single Parent

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!

Here are a number of dating “best practices” for single parents:

1. 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.

2. 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.

3. 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.

4. Engage in “What if?” conversations. Even before dating, single parents begin a series of conversations with their children that ask, “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. Smart single parents don’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.

5. 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.

6. 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).

7. 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.

8. Arrange the “meeting the kids” time with care.  Early on your kids may meet your date, 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 significant other and your kids to get together. Tread lightly at first and continue to monitor and process everyone’s fears 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 friend and their children one weekend and then have your friend 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.

9. 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 the person you are dating 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.

10. 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 your kids 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 him or her as a partner.

11. Learn all you can about stepfamily living. Nearly 20 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.