Chapter 1

Dating in a Crowd:
Dating With Purpose

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 roller coaster. 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. I just wish they would hurry up and get married so they would be a bit less interesting to one another.”

Dating in a crowd is tough. The kids are engaged, at least on some level, even when you don’t think they are. Choosing to be with one party generally means the other party is left waiting. And everyone has strong emotions and opinions about who is involved and what the outcome is—in other words, the whole family is dating. Table for twenty!

For the two people directly involved, dating is hard enough; add the kids, ex-spouses, extended family, and friends, and you better have a plan and purpose in your dating or you’ll likely waste a lot of time and wander from romance to romance with a lot of heartbreak along the way. The most consistent mistakes I see in people who have repeated failed dating (and later, marriage) relationships are these: they don’t have a purpose in dating; they lack an intentional process to their dating; they don’t have an appreciation for the complexity of dating in a crowd; they don’t take their children’s needs and feelings into consideration enough; and they don’t realize that the growing connections between children and future stepparents or stepsiblings established during dating may shift toward distance and conflict after the wedding (it’s this last truth that really catches people by surprise—I’ll say more about this later).

As we begin our journey together, I’d like to recommend a purpose for your dating and present an overall process to dating that will help you know when you’re on target for a good start. Many of the specifics of this process will be discussed in more depth throughout the remainder of the book, but I do want you to get a sense of what to expect, from pre-dating preparation, to making a decision for marriage, to anticipating the hot/cold responses of children.

Purpose in Dating

Does your dating have purpose? What do you mean, Ron? Isn’t the purpose of dating to find the right person—my soul mate? No, it isn’t. Let me explain.

I always question when I hear someone say they are looking for their soul mate, because for most people, finding someone has nothing to do with their soul or eternity. A 2001 study of dating attitudes of twenty-year-olds found that an overwhelming majority (94 percent) of never-married singles agree that “when you marry, you want your spouse to be your soul mate, first and foremost.” But only 42 percent believe “it is important to find a spouse who shares your religion.”[5] Are you kidding me? How can they remotely qualify as a soul mate and not share your core beliefs and guiding spiritual convictions? (I guess to them, a soul mate has little to do with spirituality.) Remember, single parents, this person is going to have an eternal influence on your kids. Isn’t finding someone with your same spiritual beliefs of the utmost importance?

No, apparently what the average person looking for a soul mate is really saying is, “I’m looking for the person who is easy for me to love; someone who will fulfill my needs and who knows just how to love me.” Sounds pretty selfish, doesn’t it? Soul-mate shopping is nothing more than consumerism applied to dating. The mentality is to date as many people as you can—or as one writer said it, test drive people to see which you like best—and stop when you find the one that meets your expectations and needs.[6]

The problem with this attitude is fourfold. First, it assumes the test driver contributes nothing to the quality of the developing relationship, which, of course, you do. Second, the consumer’s criteria for their purchase is completely selfish. Even if you find someone who seems to make you happy, they won’t be able to sustain it forever. This usually isn’t obvious until marriage, which is when most people begin to think, Maybe you weren’t my soul mate after all—I must have made a mistake. Third, it mistakenly places too much emphasis on your happiness as a couple and not enough on the role the stepparent will have as a parent. And fourth, the consumer attitude toward dating assumes that God has purposed marriage to make us happy. He has, but not in the way most expect.

A Match Made in Heaven: God’s Purpose in Relationships, Marriage, and Family

Our God loves us beyond anything we can imagine, and he will go to great lengths to pursue us and foster a deep relationship with us. He will even go to a cross to rescue us from the slavery of our sin. But God doesn’t stop his pursuit of us after our initial rescue. Through discipling us to be more like Jesus, he deepens our walk with him. I believe that family life is God’s best tool for discipling us. From the cradle to the grave, he is growing us up in maturity, faith, and knowledge—and he is using relationships to train us.

When we’re children, God uses our family to teach us important lessons about obedience, submission, and respect for authority. Learning these lessons makes it more likely that we’ll gain respect for God’s authority. In parenting, God teaches us about nurture, providing for those you love, and how far you will go to rescue one of your own. We also learn about free will (he lets us create life and struggle with the reality of not being able to control it!) and humility (praying for your kids will drive you to your knees!). In friendships, God teaches us about loyalty and living in community. In being single, God teaches us about trusting him with our aloneness and not turning marriage into an idol. God uses marriage to teach us about commitment, sacrifice, forgiveness, and selfless love. In the physical, emotional, and spiritual depth of sex, God teaches us about surrender, vulnerability, and oneness. In crisis, God reminds us of kingdom priorities and the limits of materialism, and he recalibrates our faith and trust toward him. And in facing death, God invites us to live in light of what is eternal. In all of these life experiences and relationships, God invites us to walk with him: “to act justly and to love mercy and to walk humbly with your God” (Micah 6:8).

In all of this, God is purposing to make us holy and healthy and eternally happy. He knows what is best for us, and each relationship and season of family life invites us to trust him and know him more deeply. And therein lies the rub. Making us eternally happy usually doesn’t satisfy our selfishness today; instead, it requires us to grow up a lot emotionally—which is painful. Ask yourself if you are open to what God is teaching you about him in your singleness. Are you pursuing him as much as he is pursuing you? Is your singleness helping you to see him more clearly and trust him more deeply, or are you instead telling him what he should be doing for you? Are you open to maturing in this season of life, or do you assume that you need marriage to be fulfilled?

And what about dating? When you meet someone, is whether they make you happy or holy the standard by which you choose to engage them? Do you lose sight of the Lord when you fix your sights on a man or woman, or can you keep your eye on your eternal love while exploring an earthly love? In what way is your purpose in dating blocking God’s purpose for you in dating?

With God’s goals in mind, I suggest that the purpose of dating for single parents is threefold:

If your purposes for dating don’t pass this smell test, slow down or stop altogether. You may be naturally attracted to someone and enjoy time together, but if after a brief dating period you are just wandering aimlessly, it’s probably time to stop playing around. If dating reveals at any point that your life trajectories (faith walk, parenting, family situations, values, etc.) are divergent, back away. This is not a game. Is it okay to date on occasion purely for recreational purposes? Yes, as long as you don’t let children get emotionally wrapped up in the dating partner (more about this in a later chapter) and the other person is aware of your intentions and the limits of the relationship. But dating is not a goal in and of itself. Instead, think of dating as the process you go through to become married. That helps to keep the ultimate purpose in mind.

The Process of Dating

Having a spiritually determined purpose in dating will help to set your attitude in the right direction. It also helps to have a sense of the process or stages of dating. Thinking through the overall process helps you to know where you are in the journey and what tasks lie ahead. It also helps you gauge the depth of a developing relationship and whether it will hold water.

In general, single parent dating will move through the following stages: It starts, if you are the single parent, by preparing yourself and the kids for dating; if you are single without children, it starts by assessing your openness to dating someone with kids and welcoming them into your life. From there, the stages consist of forming an initial couple relationship; initial dating partner and child relationships; serious dating and deepening couple and dating partner-child bonds; making decisions about marriage; and preparing for a wedding and blended family living.

Dating Process FAQs

From a stage perspective, the dating process is straightforward and clear. But questions about managing the process abound. The following are some frequently asked questions with answers that give perspective to the journey.

But before diving into the FAQs, let me speak about a perspective to avoid. Society has created many unspoken benchmarks for dating couples. They are meant to help individuals gauge the dating process, but most of them are ambiguous, simplistic, and shallow. Don’t let these questions guide your thinking about your dating relationship: Is this person good-looking and do I get points just for standing beside them? Are they wealthy or do they at least have the potential to become wealthy? Do they hang out with the right people? Are they sexually experienced (because I don’t want to be with a novice)? Have we had sex yet and how good of a lover are they? Why don’t we stay over at one another’s place on occasion to test the waters a little? Are we ready to live together?

These are the clear standards by which Cosmo, Facebook, and Hollywood judge dating relationships, but let me be clear: They are pathetic pathways to commitment, horrible benchmarks to gauge relational quality and stability, and often lead to relational self-sabotage. Don’t adopt them or be taken in by their salacious promises.

Now, back to the FAQs and their answers, which are rooted in wisdom and will help you manage each stage of dating. Hold them close and remember that when kids predate a new couple, marriage is a package deal. If you can’t marry the package, or aren’t ready to embrace all that comes with the package, don’t marry the person.

Q: If We’re in Love, Why Should We Wait to Get Married?

A: Don’t rush dating and don’t rush a decision to marry. Time is your friend. Slow the pace of your dating and fill it with purposeful conversation so you can explore how well your life trajectories might merge. Avoid being driven by surface-level infatuation, and instead look deep into the mirror to examine the person you are and the person they are.

Time will help you to see whether you and the other person are a fit not just on the surface, but to the core. Time will make known transparency or hiding, authenticity or façade, integrity or falsehood. Time will reveal what you don’t like about each other and whether you can problem-solve through it (couples who break up even once during dating are four times more likely to have relationship difficulties than couples who don’t[8]). And time will reveal whether your extended families can merge or if cohesiveness is unlikely; if both of you are parents, whether your parenting styles can complement or compete; and whether each parent is strong enough to lead their children through the transition to a new family. Don’t rush past the children and their need for reliable, consistent nurturing from you. And let the pace of your coupleness be influenced by—not controlled by—the leanings, longings, anxieties, and openness of the children.

Don’t dismiss time; she is trying to help you. Listen to her.

Q: How Do I Proceed Without Feeling Overwhelmed?

A: If you are feeling overwhelmed at this point, you may be trying to comprehend and master every stage even before you get there. Instead of trying to get your hands around all of them at once, try to focus on the stage you are in and trust God to help you manage it well. Only then do you have to deal with the next stage—and God will be there, too. It’s a little like trusting God with life.

Do you know how God gives directions? If you were to ask me how to get from my house to the local Walmart, I would give you step-by-step instructions. For example, I might say drive southwest in front of my house on London Court toward Liberty. Turn left at the stop sign. Then, curve through our neighborhood until you come to Continental Parkway; turn left. Continue east two-tenths of a mile till turning left onto Coulter Road. Walmart will be half a mile on your left. But that’s not how God gives directions.

In his book Experiencing God, Henry Blackaby says that God doesn’t give us directions that way; he only gives us the next set of instructions and then waits for us to obey. He might, for example, say, “Drive southwest on London Court,” and then stop talking. We, of course, then anxiously ask, “And then what, God?” He responds, “Don’t worry about that, just drive that direction on London Court.” “Yeah, but God, I need to know what follows that so I can get prepared.” “I’m not interested in you bring prepared.” He smiles. “I’m interested in you trusting me to know the way; I’ll give you more when it’s best.” I don’t know about you, but God’s direction-giving style really frustrates me! My need to know—and be in control—is too high for this to be comfortable. But that’s exactly why God does it that way; he wants to deepen my trust, not my knowing.

To keep from being overwhelmed by the dating stages, give yourself permission to not know how to master the next step. Trust God to lead you through when you get there. In the meantime, trust him with the stage you’re in now.

Q: Given the Magnitude of This Process, Should I Do Myself and My Kids a Favor and Wait Till the Kids Are Gone Before Dating?

A: I don’t know how old your kids are, but honestly, it’s worth considering. Essentially, what dating and marriage creates is a competition of emotional attachment and priorities between you, your children, and your partner/spouse. When it’s just you and the kids, the attachments are clear and your priority is parenting. When you begin to date, you gradually shift your time, attention, and priority to the new love; at marrige you make the ultimate shift to “forsake all others till death do you part.” Of course, this doesn’t mean you abandon or neglect your children after marriage, but it does mean that your decisions are more firmly rooted in your companion than in your children. No wonder kids feel left out and in competition with their parent’s new love. This also helps us understand why many children who at one point were in favor of their parent dating, and might have even encouraged them to marry, later begin protesting a parent’s marriage.

Whether you have kids or not, please know that dating and marriage when kids are present is a gain for you but initially a loss for the kids (until family bonding takes place—which can take years—and then becomes a gain for the kids, too). There’s no way around this truth. Single parents ask me all the time, “Can I find a new love and not make my kids feel displaced?” I respond, “Unless your children are very small and your ex-spouse is cooperative and open to you remarrying, probably not.”

Melanie wrote to me, “I seriously dated a man for a while, and my children did not like him or his children at all. While I didn’t allow my children to break up the relationship, I did spend much time asking them specifically what their concerns were and addressed them. I feel it’s critical to pay attention to a child’s response.” Jackie said, “If the child has outbursts because of a new partner, it should be talked through to find out if it’s just jealousy or something worse. A parent may have to take a step back from dating and let their child know that they are not being replaced.” Melanie is applying a great deal of wisdom. A child’s jealousy is the result of the traumatic losses they have already experienced (e.g., death of a parent or divorce, and all the changes since). They don’t want any more loss—and when you shift your energy toward someone else, it is another loss.

This is less of a concern for very young children (preschool age) because they aren’t as aware of life before and after the new stepparent. They are also more open to new people in their lives. Children between the ages of ten and fifteen seem, on the other hand, to have the most difficulty making space for a stepparent, stepsiblings, and all the transition that comes with them.[9] Waiting to date till the children are grown and on their own avoids the competition of attachment at a developmentally significant time of the children’s lives—and it’s worth considering. It allows you to focus on raising your children and preparing them for adulthood; it allows them to deal with what is already on their plate without more emotionally draining transitions being added on.

Now, I realize that remaining single in order to focus on raising your children is a challenging thought, and not many will be drawn to it. I’m just suggesting it’s worth prayerful consideration. Marriage is a blessing to the part of your heart that longs for partnership. However, remaining single is a blessing to the parental part of your heart and carries a blessing for your children, as well.

One more thought before leaving this subject. If you wait till the kids are launched from your home, please do not assume that an empty-nest blended family will be adjustment free. Every stepfamily, no matter what the age of the children, has significant transitions to manage. For example, stepparents of adult stepchildren don’t struggle because they’re trying to figure out how to discipline the children; they struggle because they still feel like outsiders to the family’s history, traditions, and rituals. And the stepchildren, even as adults, worry about how incorporating the new stepparent into their lives will impact their relationship with the other biological parent, etc. (To learn more, read The Smart Stepmom and The Smart Stepdad, in which I address adult stepfamilies and their adjustment issues.) The upside, though, is that these transitions don’t occur during the important developmental years of a child’s life and are, therefore, less negatively impactful. Because the transition to becoming a new family occurs when everyone is more mature, stepfamily adjustment does seem to be easier for most families. That adds one more reason to consider waiting till the kids are gone.

Q: Does It Matter How Long You Date Before Marriage?

A: No, and yes. Just as I used to tell people not to date for two years after their divorce or death of their spouse, I used to tell couples they should date for at least two years before deciding to marry. That was before Dr. David Olson and I conducted the largest study of single parents getting ready to marry their partners. We studied the profiles of over 50,000 couples and published our practical findings in the book The Remarriage Checkup. By the way, you can take the Couple Checkup, a similar profile to the one we used in our research, and assess your relationship. It’s a great way to get an objective perspective on the health of your relationship, which helps you make more informed decisions about the future.

In our study, we discovered what predicts great remarriage relationships (defined as a marriage in which either spouse or both have been previously married) and we learned that the length of time a couple dates does not predict couple relationship quality. That is, couples who dated a few months were just as likely to have a high- or low-quality relationship as couples who dated a few years. In other words, it’s possible to have a high-quality dating relationship in just a few months. But that doesn’t mean it’s wise to rapidly get married.

As I have already stated, when children are involved, a marriage between the two of you is not just between the two of you. How long you date matters significantly to kids and greatly impacts your future blended family. Let me remind you of the central point of this book: Coupleness does not equal familyness. You might have a quality couple relationship within six months, but that doesn’t mean your family will do well or that your marriage can’t be pulled apart by conflicts over the children, ex-spouses, or an ex-mother-in-law. Learning to steer and balance a tandem (two-person) bicycle is tough, but it’s not as challenging as bringing the Queen Mary into port. They are two different processes.

In the next chapter I’ll explain in more detail what this family dynamic is all about, but for now hear this: Even if you are ready to get engaged or marry, it may not be wise to do so until the family is ready. Someone who asks “How long should we date?” is usually already thinking about marriage, and they are hoping they can get permission to jump in. That’s why you have to remember that time is your friend—not only for your relationship, but for the needs of the kids. Children need much more time than couples, and you only shoot yourself in the foot if you ignore their timing.

Ron, are you saying that kids get to determine when the couple marries? Not at all. But it’s wise to be influenced by their degree of openness; only a fool will ignore how significant their feelings really are to becoming a blended family.

For example, teenage and adult children often scowl at a parent’s marriage when it follows a short courtship. One man, even fifteen years into his remarriage, found himself repeatedly trying to convince his two adult daughters that he really loved his new wife. Less than one year after his first wife died of cancer, the couple had met and married within six weeks. His daughters decided as soon as the wedding was announced that there was no way their father loved this woman. “How could he?” they insisted. “Mom has only been gone a little while and he doesn’t even know this new person. He’s deceived.” From that time forward, they closed themselves and would not accept the marriage or their stepmother. Time matters.

Q: If We Decide to Marry, Will Faithfully Following These Stages Guarantee Us a Successful Blended Family?

A: Of course not. There are no guarantees in life. None of us can anticipate what life will bring our way or what will be required of us when we get there. That’s why we need commitment.

Discerning your fit for partnership and becoming a family is the task of dating. Commitment in marriage is what helps you live out this discerning belief and turn it into reality. People often think if they didn’t choose well, they can’t be happily married. I’m not so sure. Don’t get me wrong—choosing well matters, but so does the commitment made by each person once they decide to marry. How else do the arranged marriages of many cultures around the world last? Commitment glues the couple together and gives God a chance to really go to work on their selfishness, mistaken expectations, pride, and immature views of intimacy.

Here’s God’s master plan for us: He asks us to vow to love, honor, and cherish, and then he uses life to teach us what we committed ourselves to. And that’s when God grows us up—as we learn how to live out our vows. Commitment is important because it gives us the chance to make mistakes while learning what God wants us to learn. Said another way, commitment is important because of what we do after we make the commitment; the power is not so much in making the decision, but in the actions we take to uphold the decision and the lessons learned along the way. No one, no matter how well they dated, knows what marriage will require of them. In 1986 when I married Nan, I had no earthly idea what parts of me would have to change in order to love her and live with her—and neither did she. God is continually growing us up, teaching us how to love one another, and molding us into the image of Christ so we can in turn deepen our love for one another. It’s a marvelous, wondrous—and painful—process! And only those who are willing to die to self and submit themselves to the discipling process of marriage receive its rewards.

By the way, this is why cohabitation doesn’t work. I’ll say much more about this in chapter 7, but it’s important to say now that cohabitation is not commitment, neither does it tell you whether your relationship would work if you made a commitment. I once coached a single parent who had been dating a man for three years. He was ready to get married, but she just couldn’t pull the trigger. When I asked if she wanted a guarantee that the marriage would last before becoming engaged, she said, “Absolutely. That’s why we’re living together instead; I want to know if this will work.”

With much compassion for her fear I replied, “But cohabitation isn’t marriage—and until you make a full commitment to each other, you’ll never know what you’d be willing to do for one another. Right now you’re just dipping your toe in the deep end of the pool; you can feel the temperature, but you’ll never know if you can swim until you throw your whole self in.” There are no guarantees in life or relationships—there is always risk. Either choose risk or don’t; when the time comes, choose commitment or don’t. But don’t sit on the side of the pool with one foot in the water telling everyone you’re swimming.

Final Thoughts

Consumer daters want guarantees. “I won’t purchase this marriage until I know my partner will love me as only my true soul mate can and is everything I want them to be—and will last 100,000 miles or fifty years, whichever comes first.” How absurd. Instead of being a consumer who selfishly purposes in dating to find the one person you believe will serve your needs, purpose instead:

Discussion Questions

1. People with repeated failed relationships often make the following mistakes. Which are you or the person you are dating guilty of?

2. What does a consumer attitude in dating look like? What should you look for to identify that attitude in yourself or someone else?

3. God is always using the circumstances of our lives to grow us up. Digest these questions:

4. I proposed three purposes for dating in this chapter. Discuss each and what it would look like to live out each in a dating relationship.

5. If you are dating a single parent, how would you know if they were not giving enough consideration to the needs of their children as it relates to dating you?

6. Society has many ambiguous, simplistic, and shallow benchmarks for gauging the status of dating relationships. How have these or others influenced your dating in the past: Is this person good-looking and do I get points just for standing beside them? Are they wealthy or do they at least have the potential to become wealthy? Do they hang out with the right people? Are they sexually experienced (because I don’t want to be with a novice)? Have we had sex yet and how good of a lover are they? Why don’t we stay over at one another’s place on occasion to test the waters a little? Am I ready to move in with them, and what happens when we live together?

7. Review the Dating Process FAQs beginning on page 34. Discuss the implications for you and the kids.