FamilyLife This Week®

Dating and the Single Parent, Part 1

with Ron Deal | January 18, 2020
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Single Parent Dating 101: How to do it successfully and what to avoid. Ron Deal offers a biblical perspective on this minefield of complex relationships and when to tell your kids.

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Single Parent Dating 101: How to do it successfully and what to avoid. Ron Deal offers a biblical perspective on this minefield of complex relationships. How to date wisely as a single parent.

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Dating and the Single Parent, Part 1

With Ron Deal
January 18, 2020
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Michelle: Recently, I was asking my friend, Ron Deal, for some relationship advice. He said that, for people who have been married, you may feel ready to start dating again; but he says there are some special considerations.

Ron: “Becoming a couple is one thing; but becoming a family is something totally different,”—which means, Michelle; and here’s the punch line—you may find somebody that you love and think you could build a life around, as a couple, but you don’t think it would work as a family. That’s a deal-breaker! I think you have to consider both things in the dating process. If you know that, on the front end, then all of a sudden, your eyes are looking for different things.

Michelle: We’re going to talk about dating and the single parent with blended family expert, Ron Deal, on this edition of FamilyLife This Week.

Welcome to FamilyLife This Week. I’m Michelle Hill. It was over a decade ago that I took the plunge into online dating; it didn’t work though. I thought I would try it again this year; and this year, well, it hasn’t worked yet;but I have met some interesting men. This time around, it has been a lot different.

This time, all the men that I’ve gotten to know, have had children from previous relationships. So, in my mind, this dating pond was very different. It got me to wondering, “What was going on in his mind?”; because I’m sure he had some questions like: “How is this going to affect my kids? Will she accept them? Am I ready for this?”

This is where you need a prayer for dating—a prayer that goes like this:

Lord, work out Your kingdom agenda in me. I am Yours. Let me be a living sacrifice of salt and light. If you bring someone into my life, who submits to Your will and will help me to love You more, then let that person be evident to me. Let me not miss Your provision. If not, let me be content with Your provision and at ease in my singleness as I seek first the kingdom of heaven. Amen.


That prayer was written by Ron Deal. Ron is a regular guest on FamilyLife This Week. He gives leadership to FamilyLife Blended® and is widely-acknowledged for his work with blended families. He’s written many books, including Dating and the Single Parent. If you’ve ever talked to him, you know that he’s an easy guy to talk to.

I got Ron in the studio to help me understand what I might be getting into if this online dating worked this time. Here’s my conversation with Ron.

[Previous Interview]

Michelle: Ron, as I’m understanding more and more about the complex issues of a blended family—you know, you’re an expert in blended families—you’ve been helping blended families just work through issues for many, many years. It’s not just when they’re married, and it’s not just when they’re engaged that they need to start thinking through these things. Quite frankly, it’s not just when they’re dating that they need to think through how to blend their family; it’s even before that!

Ron: Yes, ideally. For years, I’ve said that single parents, who do a really good job with their kids, have an easier adjustment period—not just the parent, but the children—into a blended family, if that should come down the road for them. The more a single parent understands about their journey into the single-parent world—number one and number two: what it takes to become a blended family, the better decisions they make; the better timing and pacing that they have in dating and how they move forward—ultimately, that leads to stronger kids and a stronger family.

Sometimes, based on what single parents learn, they will choose to delay dating until a season when it’s a little bit easier on their kids, for example. Other single parents will go: “You know what? I have information now, and I have a sense of this. I’m going to move through it and trust God along the way.” I just firmly believe you’re absolutely right—the more you know, on the front end, the better the process goes.

Michelle: So let’s talk about that process. How does a single parent know when they are ready to date again?—because someone is listening right now and saying: “Okay, I just want to feel love again,” or “I want to love again,” or “I just want companionship again; I want someone to talk to. I’m tired of just raising my kids on my own.” Walk us through that. How do you know when you are ready to date again?

Ron: Okay, there’s a lot to unpack there in what you just said. Those are legitimate feelings for single parents to have—feeling alone, wanting a partner/someone to share decisions with/to share parenting with, to live life with—a companion for life—that’s all very legitimate.

Let me just quickly say that dating, for a single parent, is fundamentally different than it is dating for somebody, who does not have children, and dating someone else, who does not have children—two single people with no kids. It’s fundamentally different because you’re not just creating, what I like to call, “coupleness.”

Michelle: Yes.

Ron: You also have to figure out how to maneuver into “familyness.”

It’s one thing for you to say, “I’m lonely, and I need a companion,”—that’s “coupleness.” It’s another thing to say: “And we’re going to create a family, where my children feel comfortable with their step-parent; my spouse feels comfortable with the kids—that we, at the end of the day, can function as a family.”

“How will this affect my former spouse, if that person is still living? How does this affect the memory of a deceased parent in the hearts of children?” There are so many other things to consider besides just becoming a couple. Really, this is the fundamental truth that single parents really need to hear—or if you’re dating a single parent: “Becoming a couple is one thing, but becoming a family is something totally different,”—which means, Michelle; and here’s the punch line—“you may find somebody that you love and think you could build a life around, as a couple, but you don’t think it would work as a family.” That’s a deal-breaker.

I think you have to consider both things in the dating process. If you know that, on the front end, then all of a sudden, your eyes are looking for different things—not just a person: “Oh, tall, dark, and handsome!” [Laughter]

Michelle: Yes, all those good characteristics.

Ron: But “How will my children receive ‘tall, dark, and handsome’?”—that’s a different question. It’s not to say that he’s not the right person. It’s just to say that it’s more complicated than falling in love.

Michelle: So really, it sounds like, on that first date, when you have that “interview” sort of feeling to it—

Ron: Yes.

Michelle: —that you’re having to keep in the back of your mind, “It’s not about if I could get along with this person—

Ron: Right.

Michelle: —or “If I could build a life.” It’s about whether my children could do the same.


Ron: You know, I start this book, Dating and the Single Parent, with a story. I can tell you—I’ve had this email in various forms a million times—it goes like this: “I’ve fallen in love with this guy, but he is a horrible parent to his children. I’ve just recognized that he might not be a great parent to my kids; but I love him. Is it still okay if we get married?”—you know?

Listen! The challenges that come with step-family living have to do with parenting, and step-parenting ,and boundary issues, and children who go: “Mom, we love you and we kind of like him, but we don’t love him. By the way, Dad is telling us we don’t have to love him; and if we do love him, Dad’s going to be mad at us. We’re really going to be loyal to Dad and not to your new husband. Sorry! We’re not a family.”

That’s the stuff that breaks up blended family couple marriages. If you go in, naïve to that process, and think it’s just about “coupleness,” oh, you’re going to wrestle and suffer under the “familyness” strife. So, yes!—on that first date, in the back of your mind, you need to hold on to a different set of questions. The first set is, in the front of your mind, is: “Do I like this person? Do we have a good time? Do we spend time/do we have anything in common? Is there a reason to go on a second date?” Those are “coupleness” questions. But in the back of your mind, you’re wondering, “I wonder what the family factors will be like?”

From a timing standpoint, you start with the “coupleness” stuff; but pretty quickly, you’ve got to get to the “familyness” factors and consider both. When you find what you feel like is a good combination of both, move forward; absolutely! Enjoy that relationship; put it under the grace of God and go!

Michelle: I’m just thinking of my life, and being single and dating. You don’t want to compromise. You have people, all the time, saying, “Don’t compromise.” Well, when you’re dating and a single parent, you don’t want to compromise on your convictions, but you also have to uphold those convictions for your children, and understand where your children are going and what they need.

Ron: Yes.

Michelle: That’s hard!

Ron: It is. And you know, sometimes people are willing to compromise to just not be alone.

Michelle: Yes.

Ron: You know, like you’re going out with some woman or some guy that you kind of like—but inside you know you don’t really love, and you’re probably not really going to love enough to marry—but it’s better than just being alone on a Friday night. Sometimes, I’ve seen single parents do that; and they think it’s really not a big deal for their kids.

I’ve got two big cautions around that. One is: if you have children under the age of five, little kids fall in love with adults pretty fast; right?

Michelle: Yes.

Ron: Your kids could fall in love with this new person, you’re dating and not serious about, and they can get serious about them. Then you end it; and your kids are going: “What happened?! I liked her! Where did she go?”—you know? Inside their heart, they’re just full of more questions about how people come in and out of your life. That’s not one of those messages we want them to have.

The other caution about it is: if you’re flippant about dating somebody, you’re modeling for older children what dating’s really all about and how you manage boundaries in relationships. They’re watching. You have an incredible opportunity to show them: “You know? We make choices in life, and he’s just not the right guy,” “…she’s just not the right gal; and you move on.”

Or you end up showing your kids how to accommodate, and then they make those choices; and you don’t like it when they bring home somebody that they’re really never going to spend their life with; but they’re going to hang out with: “It’s better than being alone on Friday night.”

Michelle: Right.

Ron: Yes, so again—

Michelle: —from generation to generation.

Ron: Right; right. So again, be cautious about that. Take seriously what you are modeling and the environment you’re creating for your kids.

Michelle: In your book, Dating and the Single Parent, you quote a young mom. Here’s what she said: “I chose to wait it out. I had two very angry children, who were acting out after the divorce. People told me, for years, I was wasting my life; that if I brought a man into their lives, it would help them not act out so much. I turned 50 this year. I raised them for 14 years on my own. They are adults now; the youngest of my four is 20, and now I think about dating. I am trusting God to bring a man into my life if that is His will.”

Now, I know that’s not everybody’s story—

Ron: Yes.

Michelle: —because there are many options. No one’s story is the same; but yet, she chose to do this for her kids.

Ron: Yes, I think that’s admirable.

Michelle: —and [she] sacrificed.

Ron: —and sacrificial. For some people, it is the right call. I don’t even begin to pretend that I know whether people should or should not—right?—

Michelle: Yes.

Ron: —date, move forward, blend a family. I am not God. I make that very clear; and in this book I make that very clear, but I do just present all sides. In other words, I think one of the messages in this for single parents—or somebody who’s dating a single parent—is: “It’s okay/it’s legitimate  to raise your kids by yourself and then consider dating and a new couple relationship at some point later in life when your children are a little less dependent on you. You just need to know that is an option.

Don’t let that pressure force you into—or I would say push you into—perhaps even a relationship you wouldn’t normally go into because you feel like you’ve got to give your kids another parent.

Michelle: Yes. What about the single mom out there, who might have three kids; and her children spend a weekend a month, or two weekends a month, with their dad, who has remarried? The kids are seeing this play out, one or two weekends a month, and they come home and they are like: “Well, Mom, when are you going to get married? When do we get a daddy in this home?” I mean, there’s that pressure also from, you know, yourself and the outside world, but also within your own home, with your kids going, “What about you, Mom?”

Ron: Yes, sometimes kids will say that on behalf of their parent. It’s okay, even then, to say: “Oh, I appreciate that. Come here and give me a hug! I love you, and God is taking care of us. We’re just going to trust Him with our life. Who knows? Maybe someday, that will happen.” Give them that hug and move on. Don’t feel pressured into moving down that road unless it’s really something you desire and you feel like, as you move into a dating relationship, it’s going to bless your kids.


Michelle: Some excellent words on dating and the single parent from Ron Deal. Hey, I hate to do this, but we need to take a quick break. I’ll be back with more of my conversation with Ron in two minutes. Stay tuned.

[Radio Station Spot Break]

Michelle: Welcome back to FamilyLife This Week. I'm Michelle Hill. Today, we are talking about dating and the single parent. As I mentioned earlier, I’ve recently started online dating; and a lot of the men, whom I’ve gotten to know, have children from previous relationships. For some people, they’re having to answer, “Who is this new person in Mommy or Daddy’s life?” So that’s when I asked Ron Deal: “Just when and how do you have that dating conversation with your kids?”

[Previous Interview]

Ron: If your children are old enough, and you feel like they’re going to have an opinion about all of this, then I would engage them in what I like to call “What if…?” conversations—you know, “What if Daddy started dating again? How would you guys feel about that?” Just toss out that question over dinner one night. See what happens; watch the reactions; learn something about what’s inside your kids; and then move on. Take it as a grain of salt.

I call this “assessment and intervention” all at the same time. It’s assessment in the sense that you’re learning something about what’s going on in your children. By the way, if you’re asking, five dates in and they’ve already met the guy, now their answer is based on what’s happening

Michelle: Yes.

Ron: —not on the hypothetical, “What might happen.” So ask beforehand if at all possible; right? Somebody listening to this right now, went, “Oops! I’m already dating.” Okay, start now! [Laughter] It’s okay, so start now.

You get assessment—you learn something about your kids. You’ll have one kid, who goes, “Oh! I think that will be great!” Another kid says, “What!? No way!” You will find out pretty fast what kids think. But it’s also intervention in the sense that you are planting a seed to tell them, “This may happen someday.” It doesn’t mean that they’re automatically going to be okay with it when it does happen, but you gave them a little warning; right? You’re still the parent; you’re still the adult. You get to make those decisions, and you gave them a little warning.

If you have repeated “What if?” questions:

“What if—do you see that guy over there? You guys know him from—you know his son” or “daughter from school, right? We see him at the soccer field: “What if I went out on a date with him?”

”Well, we’re going out on Friday night, so how do you guys feel about this whole thing of me dating that person?”

“Well, we’ve been out three times. I’m thinking about going out with him again. What do you guys think about that?”

See, the “What if…?” just keeps going; right?

Michelle: Yes.

Ron: “What if I got married to him?”

You know, eventually, over a period of weeks, months/years, there’s a series of “What if…?” questions that are checking in with your kids. Now, note, you are moving toward the heart of your children in this process. There’s a paradox here, Michelle. When you move toward your children, as you’re moving toward another adult, you’re giving balance to what needs to happen in the blended family.

Michelle: Now, when is the appropriate time if—let’s say you’re dating—when is the appropriate time to bring this person into your kids’ lives and still try to shield your kids, you know, from them falling in love before you are?

Ron: Yes, good. So again, developmental considerations are one little piece of this. Really young kids fall in love with adults pretty fast. You need to be really careful about exposing children, under the age of five, to a new dating partner. I wouldn’t expose them to that new dating partner until you really felt like there was some future here: “Now we need to take the next step”; okay?

With elementary-aged and teenagers, you can’t always orchestrate when and how they discover one another or how all that happens. Sometimes by accident, they just see each other. Again, the soccer field meeting; they see what’s happening across the room. I talked to a couple, just the other day, whose kids figured out that their parents had crushes on each other before the parents figured it out; you know? [Laughter] They were talking at school about, “I think my dad likes your mom.”

You can’t always orchestrate those things. That’s why it’s pretty good to do the “What if…?” dialogue; because when it happens, you’ve already got an open conversation around this.

Michelle: Yes.

Ron: It’s nothing new. We don’t have to pull this out and somehow make it all nice and pretty; we’ve already been talking about this stuff.

In terms of saying, “Alright, my three kids are going to spend the afternoon with this guy I’ve been dating,” / “…this woman that I’ve been dating for a while,” I think you can just pick an activity that everybody enjoys.

Michelle: Yes.

Ron: It’s kind of like dating; now, the kids and adults are dating a little bit. We’re going to find something to do, where we can be around one another and enjoy each other’s company a little bit; so you do that.

Well, you know, that’s a nice place to start. It’s kind of like dating another person; you go out and have dinner and a movie. But eventually, you have to get past the fun stuff, and you’ve got to get down to: “How do you feel about life? What’s your outlook on life and your worldview?”

So you start with those easy things and then you begin to move to just more time around one another/around real-life activities. You’re watching, and you’re listening, and you’re absorbing. You’re checking in with your kids when that evening or that afternoon is over: “How did that go for you? What was that like? What were you feeling?” You’re kind of bringing them along. You’re constantly moving toward them while you’re also moving toward this other person. It just helps inform the next decision.

Michelle: Yes.

I want to throw out a scenario here. Let’s say that Susie is sitting in the room right now with us. She was married for many years; she’s divorced. She feels like she’s ready to move on. She meets this guy; she starts dating him. She soon goes down this path of marriage in her mind. They haven’t talked about it; but in her mind, maybe she’s thinking about it too soon. How would you counsel her to keep her feelings in check?

Ron: First of all, you’ve got to recognize what’s going on inside, you know? You find yourself thinking a lot about this person—you know, all that infatuation stuff. What hits you in seventh grade is also what hits you when you’re 45!—[Laughter]—right?

You’ve got to recognize that for what it is, and talk to it: “Alright, self, right now you’ve got this fantasy that has developed really fast. There’s a dream behind it, and you’re motivated to make it happen.” We need to relax a little bit on this. We need to slow down the process a little bit and keep praying. In the book, I call it “The Dater’s Prayer.” You know, it is that:

Lord, I am Yours. I’m trusting You with my life, now, as a single person. If You bring someone into my life, let me be objective about that. Let me see them through Your eyes. Let me continue to trust You, not fall in love with the fantasy that they are going to fulfill me in this world.

That prayer helps you stay grounded.

Michelle: That’s good.

Ron: Having friends is really helpful, too, because they can give you some objective, outside point of view about what you’re doing, and how you’re acting, and help you recognize how strong the infatuation might be.

Michelle: And that’s got to be hard; because I’m also thinking, “What if she has—what if Susie is dealing with a teenage son, who needs a strong father figure?”

Ron: Yes.

Michelle: That would be way too easy to say, “This is it!”

Ron: Yes, right; again: “We’re going to plug in this person. We’re going to hire some—I mean, marry somebody to parent my…” [Laughter] Did that just come out of my mouth!? [Laughter]

Michelle: Yes!

Ron: That’s kind of funny how that happened—a little Freudian slip on purpose there.

Michelle: Yes. [Laughing]

Ron: Yes; you know, honestly, sometimes that’s the way people approach this—like: “I’ve got to give my son a dad!” No, you don’t—and not in that manner—okay? Take your time! The slower pace, where you’re checking in with everybody and you move into deepening relationship—not just as a couple, but with the family factors in mind—then, when you make a decision toward marriage, you’re still going to have adjustments. It’s not reality until everybody moves into the same house together—like it ain’t real until it’s real! But the process of moving into reality is far better for everybody involved.

Michelle: Yes; this sounds hard.

Ron: Yes, it is!

Michelle: As you’re talking through it, I’m just thinking, “There’s so much to keep in mind; there’s so much to filter through.”

Ron: —“and to continue to pray over!—

Michelle: Yes!

Ron: —“constantly, at every step along the way.”

Michelle: I don’t have enough time in my day for that much prayer.

Ron: [Laughing] I’m with you. [Laughter]

Michelle: I’m just saying!—it just sounds very complex.

Ron: Yes.

Michelle: I think we, as humans, don’t consider the complexity of all that we’re working through. When we have a goal in mind, we have steps that we need to take in order to get to that goal; and we have people we need to keep in mind as we do that.

Ron: Let me just give you a couple of little stats, just to give you some perspective about why we’re saying, “Take your time with this complex process.” Number one, children who feel like they’ve been included in a decision toward their parents’ marriage and forming a blended family have an easier adjustment period after the wedding. If they feel like they’ve been included—not overrun, not left behind, but they’ve been a part of the process—it makes a difference.

Number two, depending on the study that you read—one study that I did with David Olson for a book we wrote, called The Smart Stepfamily Marriage—we found that less than two-thirds of couples, probably even half of dating couples, have a serious conversation about how they’re going to parent after the wedding: “How we’re going to parent and step-parent together—my children, your children, our children”—whatever the scenario is—less than half!

Guess what? One of the biggest factors determining the success of a marriage and a family, after the wedding, is how you parent together; so if you don’t do the work on the front end, you’re just asking for trouble on the back-end. That’s why dating well really matters. If you date well—if you maneuver through the process at a pace, where children come along; adults feel greater confidence in their “coupleness” and the “family-ness,”—then, when the marriage happens, you really get to reap the rewards.

Again, no promises of “Everything is easy,”—I’m not saying that!—but it’s much easier, and less complicated, and less troublesome. I think it’s worth counting your calories on the front end instead of just having to burn off all the fat later on.


Michelle: That’s just Day One of my conversation with Ron Deal. We’re going to talk more next week about dating and the single parent, because there’s a lot more to talk about! Ron and I will be playing a stoplight game. We’ll find out who is worthy of the green light in dating; or the yellow caution light; or the big, fat red “No!” I hope you can join us for that.

Thanks for listening! I want to thank the president of FamilyLife®, David Robbins, along with our station partners around the country. And a big “Thank you!” to our engineer today, Keith Lynch. Thanks to our producers, Marques Holt and Bruce Goff. Justin Adams is our mastering engineer, and Megan Martin is our production coordinator.

Our program is a production of FamilyLife Today, and our mission is to effectively develop godly families who change the world one home at a time.

I'm Michelle Hill, inviting you to join us again next time for another edition of FamilyLife This Week.


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