FamilyLife This Week®

Dating and the Single Parent, Part 2

with Ron Deal | January 25, 2020
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Michelle Hill tosses tricky dating scenarios to Ron Deal who offers insight into whether the single-parent situation in question is a red light, a caution light, or a green light.

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Michelle Hill tosses tricky dating scenarios to Ron Deal who offers insight into whether the single-parent situation in question is a red light, a caution light, or a green light.

Dating and the Single Parent, Part 2

With Ron Deal
January 25, 2020
| Download Transcript PDF

Michelle: In the process of dating and remarriage, Ron Deal says people tend to overlook many differences—differences that could cause significant problems.

Ron: So many of the signs and symptoms, of what will eventually come to be, you can learn from, hearing somebody’s past and seeing how they deal with co-parenting issues with a former spouse in the present. I just think a lot of people don’t really listen. You know, their need to get married pushes out common sense. They see those things, but they don’t pay any attention to them; and they just kind of minimize them.

Michelle: We’re going to take a look at those warning signs associated with dating and remarriage as we tackle the subject: “Dating and the Single Parent” with Ron Deal on this edition of FamilyLife This Week.

Welcome to FamilyLife This Week. I’m Michelle Hill. Dating is hard work. According to Wikipedia, the main purpose of dating is “for two people to evaluate one another’s suitability as a long-term companion or spouse. Oftentimes, physical characteristics, personality, financial status, and other aspects of the involved persons are judged. As a result, feelings can be hurt or confidence shaken. Because of the uncertainty of the whole situation, the desire to be acceptable to the other person, and the possibility of rejection, dating can be very stressful for all parties involved.” [Sigh] Sounds exhausting; right?!

Keith: [Softly] Thanks, Wikipedia!

Michelle: [Laughter] It is exhausting!

Now, I want you to imagine getting out there in the dating world again after being married for a while. If that is you, you know [the] questions racing through your mind are: “Will I ever find love again?” “Will the kids be okay with him?” or “…her?” “How do I do this dating thing again?” “Am I ready for this?” “Will I make the same mistake I made last time?”

We are answering these questions and more today with Ron Deal. I’m so thankful for Ron! His knowledge and expert advice give me tools and ideas. As always, he gives his advice through the lens of faith. Ron is a licensed marriage and family therapist. He’s a professional counselor; frequently appears on national media like Fox News, MSNBC, WGN, Focus on the Family, FamilyLife Today, and FamilyLife This Week! Okay, I know.

Here’s my conversation with Ron Deal about dating and the single parent.

[Previous Interview]

Michelle: Let’s talk about the mechanics of dating. I want to start off our conversation with your red light and yellow light and green light examples, because I think that is a great way to start thinking about things, especially as you’re dating. I’m going to throw out a couple of scenarios from my life—

Ron: Okay.

Michelle: —and my experience of dating a single parent, and just ask you, “Red light?” “Green light?” “Yellow light?”

Ron: Got it.

Michelle: Obviously, I’m still single. I’m not dating anyone right now, so I went through all the red lights! [Laughter] There have been no green lights.

Okay, first question or first scenario: You’re on a date; and when you ask that simple question, “Hey, so tell me about your life,”—you’re just trying to get to know somebody—“Where have you lived? Where’d you grow up?” And it turns into a biography of their life with a detailed topic of their ex- that lasts through the rest of the evening.

Ron: [Laughter] As in almost like a monologue?

Michelle: It was a total monologue.

Ron: Wow. Yes, I would say that’s a yellow light—

Michelle: Okay.

Ron: —because it suggests to me that they haven’t worked through some of the pain related to that backstory. It doesn’t necessarily mean “red light,”—“No, this person is in trouble; you don’t want to partner with him.” It just means, “Learn some more.” That’s what yellow lights mean, by the way: “Slow down; take some caution. You can still proceed forward, but you’re watching carefully; because you’re not sure if there’s something around here.”

For example, in the best-case scenario of that, it could just be that they’re talkative. [Laughter]

Michelle: It’s true!

Ron: This is an expressive person, and they have a few thoughts, and they just roll with it; and they’re a talker! Who knows if that’s a quality you love or don’t love.

The worst-case scenario is the fact that there’s so much rolling out—and by the way, if it’s kind of laced with resentment, and some animosity, and there’s some bitterness kind of dripping off of all of these stories, it’s telling you something about their heart, and their sadness, and where they are.

Here’s the thing I would want you to know: Anger and hurt can tie two people together as tightly as love can. There are a lot of former spouses that are still “married,” if you know what I mean. Their anger and hurt is so real; they are still emotionally tied to one another—

Michelle: Yes.

Ron: —which means neither one of them—the person you’re dating, especially—

Michelle: Right.

Ron: —is free to really give themselves to a new relationship and be objective about a new relationship.

You want to date somebody, Michelle, who is totally objective about you

Michelle: Yes.

Ron: —not somebody, who’s going: “Oh, Michelle is so not my former spouse!” “She’s so not my ex-wife!” “I’m so glad she’s not my ex-wife!” That’s not a good scenario; you’re being judged based on the former.

Michelle: Yes.

Ron: That’s not objective; that’s reactionary. Are you with me?

Michelle: Yes!

Ron: That is a huge yellow light. If it stays that way—you continue to date; you just see that over and over and over, and you kind of hear more of the story—I would go, “That turns into a red light.”

It’s listening beneath the words to, “What is this telling me about where there heart is?”

Michelle: When is the appropriate time to share those details of an ex-spouse?

Ron: Well, you know, on some level, on a surface level, it’s part of life; I mean, even, you know, “Tell me about who you are, and—

Michelle: —“and what kind of shaped you!”

Ron: Right; “Yes, I have children,” “Yes, I’ve been married before,” “I went to college here.” You know, it is a fact of a person’s history; so it’s appropriate, I think, to hear those things, early on, in your dating experience.

How much you share about the details of that, and how you feel about all of that, and what the emotional residue is still in your heart as a result of those relationships—you have to have a little bit of trust between you, as a dating couple, for them to even want to reveal that sort of thing.

Michelle: Yes.

Ron: So I would assume that would come after a few dates, assuming you’re both interested in one another; your conversation’s beginning to deepen; yes, I think it’s even time for you to begin to probe: “You know, you’ve shared a little bit with me about this. I’d like to hear more about that. What’s the reality of that for you?”

It’s not just—for example: “How do you feel about your former spouse?—how that marriage ended?”— those are details you want to know; for example, “Did the former spouse run off and leave this person you’re dating?” “Did this person you’re dating try, for five years, to save the marriage and couldn’t?” “Did they wish, to their dying day, that they could have?” Yes, that person’s still emotionally tied; are you with me?

Michelle: Yes.

Ron: I mean, that’s stuff you want to discern. Or, were they the ones, who kind of said, “I was done; here’s why”; and “Here’s the backstory to that”? Again, all of it is just information. It doesn’t necessarily add up to good or bad; but it does tell you something about who they are and where they are, and their readiness for a new relationship.

The other piece is, you know, that former relationship, also—if they have children together—is a co-parenting relationship that lives on today and will live on for the rest of your marriage, if you guys get together. I’s not just, “How do you feel about your former spouse?” but it’s, “How do you function as parents? What’s that like?”

Michelle: Yes.

Ron: “Well, pick up and drop off is horrible! We just fight all the time—every time that happens!” You want to know that, because you’re marrying that conflict.

“We never talk. You know, the kids go over there; and I just communicate through my kids. I can’t stand dealing with my former spouse, so we just don’t.” That, too, tells you how deep the hurt and pain is, and you’re marrying that. That also tells you something about how this dating partner deals with conflict—they cut people off.

Michelle: Yes.

Ron: So many of the signs of symptoms, of what will eventually come to be, you can learn from hearing somebody’s past and seeing how they deal with co-parenting issues with a former spouse in the present. I just think a lot of people don’t really listen. You know, their need to get married pushes out common sense. They see those things, but they don’t pay any attention to them; they just kind of minimize them.

That’s kind of true of human nature: During dating, we minimize differences.

Michelle: Right.

Ron: And after the wedding, we exaggerate them! [Laughter]

Michelle: Obviously, what I’m hearing is: “Those are character flaws.

Ron: Yes.

Michelle: “Those are huge character flaws.”

Ron: And they’re relational flaws.

Michelle: Yes.

Ron: It’s not just about the person, and what kind of person they are; but it’s their relationships and how they deal with relationships. So, yes; both character flaws and relationship flaws are yellow lights, at least. If they persist, they’re red lights.

Michelle: Okay, next light. So you’re on a second date—on a drive with your date, and your date drives you past their ex’s house—

Ron: [Laughter] Okay!

Michelle: —and not just drives past— points it out.

Ron: Okay.

Michelle: And then turns around and points it out again. [Laughter]

Ron: Oh, my goodness! [Laughter] For what purpose?—may I ask? [Laughter] Are we just going, “Hey, I just want you to get a good look at where they live”? [Laughter]

Michelle: Yes.

Ron: Okay.

Michelle: And this was not on the main drag.

Ron: They went—

Michelle: This was out of their way, in a cul-de-sac; hence turning around, I guess.

Ron: Okay.

Michelle: That feels to me like someone is still hung up on someone, or someone is trying to show someone that there’s someone new in the picture. It just—it was very confusing.

Ron: Yes, yes.

Michelle: Green light? [Laughter]

Ron: No, there’s no green light there. There’s, at least, a yellow light. [Laughter] There may be a red one. [Laughter] Again, it’s like: “Okay, I’ve got to get really curious about this! What is this telling me about this person?” and “What’s their need?” and “What were they doing?”

If you had a conversation, and—I guess, the green light scenario would be: “We were talking about it.” And you were pressing, “Now, where does your ex-wife live?” “Well, she lives over there. . .” “No, no! I want to know! Where does she live? Does she live on this street or that street?”—you know, you were pressing into it, and then they drove you by to see the house, that’s a green light; there’s context there.

But this is like, “No, I have a need for you to see where she lives, and to dialog around that.” You know, if it was a metaphor—here’s a good question to ask yourself when you’re dating somebody, no matter what has just happened: “If this were a metaphor, what’s the message? Is the message, ‘I stay attached to where my former wife is’?” “Ooh! Yes; no thank you. God bless you—moving on!”—that’s a red light.

Michelle: Okay. Well, that’s all the dates I had with that one.

Ron: Good for you! Good for you! [Laughter]

Michelle: Okay; next one, your date discusses marriage on the first date.

Ron: Marriage with you?

Michelle: Marriage with me.

Ron: In the sense of what?

Michelle: “Let’s go off to Vegas tonight.” [Laughter]

Ron: No; run! Do not walk; run away from that relationship. This is the opposite of the sign at the swimming pool: “Run; do not walk away from there.”

Again, that shows you desperation. Desperation is a horrible way to make decisions. You are not objective about yourself; you are not looking at the quality of the relationship. You’re not judging it based upon anything real. It’s based upon some pain. Never make decisions out of pain.


Michelle: Ron Deal, giving some excellent advice about not making those decisions out of pain. Sometimes, that’s a really hard place to be; isn’t it?

Well, we need to take a break; but when we come back, Ron Deal is going to continue helping us make good decisions. Stay tuned. We’ll be back in two minutes.

[Radio Station Spot Break]

Michelle: Welcome back to FamilyLife This Week. I'm Michelle Hill. We’ve been talking about dating and the single parent. Actually, we also talked about that last week. If you missed last week’s show, go to the website,; that’s

Let’s head back into my conversation with Ron Deal. We’ve been talking about those bad decisions in the midst of the pain.

[Previous Interview]

Michelle: A lot of my dating of single dads has come through some online dating apps.

Ron: Okay.

Michelle: One thing that I noticed was a lot of these guys would say, “Yeah, my ex-wife just remarried.”

Ron: Yes.

Michelle: I would go, “Okay, so what are you doing right now?” “Well, I’ve got to either get a dog or fill this space.”

Ron: Oh, wow! Yes.

Michelle: That’s one thing I was noticing—was pressure to really speed things up. You’re sitting there, listening to some of these stories; and in the back of your mind, you’re like, “Is this smart?”

Ron: Yes.

Michelle: “Not?”

Ron: Yes.

Michelle: I didn’t have the red light, green light, yellow light illustration in my mind at the time.

Ron: So you ask yourself, “If what just happened is a metaphor, what’s the message?” He’s looking for a dog! Are you going to be that dog? [Laughter] I don’t think so!

Michelle: I don’t have the locks of a Golden Retriever, so—

Ron: You know, this is a guy, who’s kind of saying: “You know, she’s moved on. I’ve got to find something. It’s going to help me break away from her,” or “I’ve got to spit in her face the way she just spit in mine.” You know, whatever the message is, it’s not a good one. “I just need a companion to help me feel better about me.” [Laughter]

No! You never marry—okay, here’s my favorite worst quote about dating. The movie is Jerry Maguire. She says to her sister about Tom Cruise: “I love him for the man he almost is.”

Michelle: Yes.

Ron: That is the wrong reason to be attached to somebody, because the person they aren’t is not who you get when you get married! You get the person they are;right? So that fantasy thing of: “This is going to somehow complete my life/make life okay. It’s all going to be good! We’ll work it out in the end.” No, no, no! That’s unrealistic—an expectation that just sets you and other people—and children—up for more hurt and pain. We don’t need any of that.

To that person, I would say: “Well, I appreciate your interest. Maybe at some point in the future, we could re-visit this; but I think right now, I’m not interested.” What’s that about? What you’re saying is: “I don’t know what’s going on with you right now; I’m not going to take responsibility for it. I think you need some space to figure this stuff out. If you go find a dog, and that helps, then in six months or a year—you’re still open and you’re in a better place, emotionally—I might be willing to date you. But right now, it’s not good timing.”

Michelle: That’s really good advice. I wish I had had those words.

Ron: You know, at the base of all this is a sense of your self-worth and esteem and knowing who you are in Christ. I mean, sometimes I think we overplay that; but I really do think it’s so important to just say—you know, if I’m saying  the Dater’s Prayer—“‘Lord, You have me in the palm of Your hand, and I am okay with You. Help me navigate my singleness. If You bring somebody into my life, help me recognize that and navigate it. And even then, may You be first and foremost in my heart.’”

If you’re living out that Dater’s Prayer, you have the ability in that situation to say: “Thank you, but no thank you. I don’t need what you’re not able to offer.

Michelle: Right.

Ron: “I have what I need.” That empowers you to see the yellow lights for what they are and certainly recognize when a red light has come on.

Michelle: Yes. Okay, I have one more light. Let’s just say that there is someone, who has a mom who wants him to remarry, and to remarry soon; but this time, the “better girl.”

Ron: Woo! [Laughter] Okay.

Michelle: You’re sitting down to dinner, and mom keeps texting. He refuses to shut off his phone, and he keeps answering her.

Ron: Okay; so if what’s happening in front of you is a metaphor, what’s the message? The message is—he’s got a strong attachment to his mom and is unable to say, “I love you, Mom, but please stop,” which means you’re marrying that! Do you want to marry that? I don’t think so. You want to marry [a person] who is clear of their emotional attachments, and their loyalties, and their obligations to the point where they can offer you all of them.

Now, you might go out on a second date or a third date, just to see, “Is this a one-time deal”—the whole mom texting thing—“or is this a pattern?” That brings up a good conversation. One thing doesn’t really tell you much of anything, but two times/three times is a pattern. Patterns are really hard for people to break. Patterns you should pay attention to, because they tell you something about how the person exists over time. If, after a second or a third date, you continue to feel mom’s presence in the room, when you’re with this person, I think that’s a red light.

By the way, we could apply this same principle to—you know, here’s a “familyness” red light. You start dating somebody that you think is a great person: they’re a hard worker; they’ve got a great career, make a lot of money; they’re godly in every way that you can see on the outside and inside; and they just happen to be a really lousy parent. You know, that’s, at least, a yellow light, because when you marry them, and become a step-parent to their kids, you’re going to inherit that parenting process and dynamic; and you’re not going to be able to fix it.

I’m convinced that a lot of what we call “wicked stepmothers” and “abusive stepfathers” are just people, who are trying to fix what their spouse refuses to fix in the kids; you’re just trying way too hard and you don’t have the power to make it happen. Know that, going in!

If you see that—and, by the way, even as these words come out of my mouth, I recognize: “This is a bit of a shame. If you find somebody, who is a wonderful person—there’s so much potential for your ‘coupleness,’ but there’s just a lot of difficulty in their life in parenting and kids—it’s a shame that that would need to be a yellow light/perhaps a red light—but it is what it is. You can’t marry them for the person they almost are.”

Michelle: That’s a good point.

Ron: You need to know who they are.

Michelle: So, Ron, let’s say it’s a yellow light or it’s a green light, and we continue to get to know this person. At what point is a DTR—a “define the relationship”? And does that happen more often in these types of relationships?—in a sort of blended dating relationship?

Ron: Yes, I think so. “Define the relationship” is a conversation around: “You know, here’s where I am as I think about this relationship. I’m wondering where you are as you think about this relationship.”

At some point, that turns into: “Hey, I need to define our relationship in a new way. The other day, you corrected my kids when we were on that outing. I just want you to know I’m not ready for you to do that yet. I just need you to talk to me, and I’ll be happy to try to take care of something; but I’d rather you go through me rather than doing it directly.” So that’s a DTR conversation—

Michelle: Yes!

Ron: —you didn’t know to have until something happened. Yes, alright; use that as a springboard into continuing to deepen your relationship. By the way, what’s the value of doing that? When you set a boundary with someone that you’re dating—and if they say: “Well, no; I don’t care what you say! I should be able to tell your kids to stop doing whatever,”—you just learned something really important; right?

I mean, this helps bring to the surface different pieces of the puzzle to help you get objective information and decide how to move forward. If, on the other hand, the person says: “Oh, you know, you’re right. I’m sorry. That’s not my place,” they can recognize their place and what it is and what it isn’t. They can learn—that’s a good quality. You just learned something positive that you needed to know.

Sure enough, the next day they come to you with, “Hey, would you mind asking your kids not to throw my glass vases around the living room?” “Yes! Thank you for coming to me.” [Laughter] Like, “That’s a legitimate need.”

Michelle: What kids are throwing glass vases? [Laughter] Sorry, sorry—it is a legitimate need, Ron; I’m just—[Laughter]

Ron: Exactly! And now, you have something that you need to take care of. By the way, if this dating partner sees that you are unwilling to stop your kids from throwing glass vases, they just learned something about you they need to know. This helps everybody move forward in the relationship. You’re learning what you need to learn about one another.

At the end of the day, either you’re gaining confidence in your future, or you’re losing confidence in your future. Now, sometimes, you’re just kind of maintaining the confidence you have—it’s not really going up or down—okay, keep dating! But if it’s going down; yellow lights are turning pink—[Laughter]

Michelle: —pretty soon they’re orange.

Ron: —pretty soon they’re orange, and then they’re red.


Michelle: So you’re defining the relationship; the relationship’s going well. You’ve been dating three months/four months; the kids love the person; and you’re thinking: “Okay! This is great!

Ron: Yes.

Michelle: “Let’s just jump in!”

Ron: Okay.

Michelle: Is that really good advice?!

Ron: You know, I really hate trying to put a time frame on dating. People have pressed me for that: “How long should we date?” I don’t know! It depends on the age of the kids, where they are: “Is the oldest one in college?” “Are they out of the house?” “Are they really young?” “How about you? What have you been through?” “What about this person you’re dating—what have they been through? Have they been through three divorces, and are they really needing time before they make another commitment?”

All of that stuff matters; okay? And let me just say—after three or four months, you can be ready to get married; but your kids may not be ready for you to get married.

Michelle: That’s a good point.

Ron: So we need to slow it down; we might start making plans, but they’re off in the distance. We’re not going to move toward co-habitation; that just confuses everybody—there are so many things around that. Just spiritually, that lacks obedience; but practically and relationally, it just makes things messy, I think. You need clarity, not ambiguity, in this relationship. Clarity is: “We’re dating; we’re not together”; and then, “We’re married, and we are together,”—that’s clarity! Moving in together just adds ambiguity.

Take it a step at a time. Surround yourself with other people. Have a mentor: find a couple, that’s a blended couple, that is five, seven, ten years down the road further than you—they’re already married—and take them to dinner once a month. Pick their brains, as a dating couple, sitting with another married couple, going, “What do we need to know that we can’t see, that you guys can see at this point?” Surround yourself with all of those things to help you either, again, gain confidence or maintain; or if you start losing confidence, that’s information you need to have.

Michelle: Yes, great advice! Thanks, Ron.

Ron: Yes, glad to be here.


Michelle: That was my conversation with Ron Deal about single and the dating parent. Ron gives leadership to The Smart Stepfamily® and also FamilyLife Blended®. It’s his goal to help blended families thrive. Most of our conversation today came out of his book, Dating and the Single Parent. If you want to hear more from Ron, he has a podcast, FamilyLife Blended. Why don’t you just go to our website,——and there’s a link to Ron’s podcast. It’s worth your time!

Hey, thanks for joining me today! Next week, we’re going to talk a little bit more on singleness. We’re going to hear from Lisa Anderson; and with her quick wit, I can guarantee a laugh or two! We’ll also hear an epic love story from a young gal who adopted 14 girls before finding her prince. It’s a blended family story of epic proportions. 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. 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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