We recently asked for dating questions on social media, and you guys filled us up with all kinds of questions. Dating is hard, period. And there’s no manual, there’s no right way of doing things. And on top of that, when you’re a single parent, it gets even trickier. You have kids now, plus dating has changed significantly in this digital age. So how can single parents navigate dating and all its complexities? 

What’s the hardest thing personally for you about dating as a single parent?

Amber’s the expert. I feel like I’m becoming an expert because it takes a lot of time. What is the hardest thing about dating as a single parent? I think it’s a lot like Goldilocks and the Three Bears. You have to take a lot of bites of oatmeal before you find the one that’s just right. You’re constantly out there, you’re getting your hopes up. It’s like, “Oh, this might be, oh, this seems pretty good. This seems pretty good.” And then you’re going up the rollercoaster and then crash because it’s just not the right fit. And then you have to think, “Oh, am I ready to ride the coaster up the hill again and then crash?” And so it really requires a lot of tenacity and resilience and groundedness to not go dead inside.

We at this table are all in different states. Marissa and I are both remarried while Amber and Elizabeth are not. And so we’ve all had different experiences with this. We’ve all found love or haven’t found love in different ways. And so instead of doing an episode saying, “Well, here’s how you approach dating” (and we’ve done some really good episodes in the past on red flags, green flags, yellow flags), today we thought we’d just get into it with you all. 

How does one know when they are ready to date? Do I even want to venture into it? 

It is a good question, and it’s really individual. So I don’t think there’s necessarily one specific answer, but I think some things that come to mind for me hearken back to our episode “Is It Love or Loneliness?” So listen to that one. If you’re really in a desperately thirsty place, you will drink anything. If you go to the grocery store hungry, you’re going to buy a lot of junk food. I think if you’re really lonely and empty, it may not be the best time to date. 

So I’m recently out of a long-term relationship, and I was actually thinking about this this morning because I’m going through a breakup recovery course. And one of the things that he talked about in the breakup recovery course was how you had all these things that you were giving to this other person: your time, your energy, your love, your this, your that. And the hardest part for people is finding what to do with all of those things that you were giving away. And you almost feel like a lost little lamb. Like, “Well, what do I do with all this?” And I thought that was a really great perspective. And so I’m thinking about what you said, and it’s like you have all these things that you want to pour into, and that loneliness is tricky. I know I’ve done crazy things in loneliness. And so it’s like how do you navigate filling up those holes in a healthy way versus trying to plug in another human body? And so I’m just thinking about all the ways that I’m trying to fill those. What are some intentional ways that I can fill those gaps? And then when someone comes along, eventually they’re just kind of adding to—they’re not filling in gaps and holes. Does that make sense? I don’t know if that’s the right way to approach it.

I think both of you hit the nail on the head, at least from my perspective. I’ve been remarried for over 10 years now and I didn’t date a lot. In fact, the reason I started dating is because a friend of mine who was really close to me said, “So why do you say you want to be married again, but you’re doing nothing about it. What are you going to do?” And I’m like, “Well, my life is so busy. Where am I going to go? I’m going to go to a bar. Am I going to go to a church? I don’t want to go and try to hook up with people at the church and go, ‘Hey, do you want to go out for coffee?’ And it’s just kind of icky.” So I didn’t do it for a long time, and I think that I became unhealthy because I didn’t. So I want to wear a badge and go, “I waited for X amount of years to do all my healing.” And I think that’s true. To your point, Amber, if we’re just quelling loneliness, that’s not a reason alone to date. But putting yourself out there, understanding dynamics, getting in the dating pool, I think is a healthy thing to do. And I didn’t do that. So my point is there’s no one size fits all. But I do think a cornerstone is what you’re talking about. Don’t do it just out of loneliness. There are other ways, to your point, Elizabeth, to deal with loneliness or the stuff that you’ve got that you want to give.

Someone asked how it has gone for others waiting to date versus not waiting to date. So maybe we can talk about what is appropriate for waiting to date. 

I waited about two years to begin dating, and is there an exact right time? I don’t think so. But two years felt right to me at that time. I had gotten over some of the initial devastation of divorce. I was getting into a new normal. My kids were more settled. We may circle around to that later because while I thought they were more settled, they really weren’t ready for me to date. But I did feel individually ready. And for me, it happened to be two years.

I wonder, and this just popped in my head, I know all of your stories here and I know a lot of other single parents obviously, that I know in varying stages of when they dated versus didn’t date. And some people just jump right into it and that kind of thing. I wonder if a rule of thumb might be to allow yourself one full year of seasons before you even start dating—go through Christmas, go through New Year’s, go through Valentine’s Day, go through birthdays, go through Father’s Day, so that you’re covering all those bases. So maybe a good place is just don’t date in the first year. Allow yourself a full round of seasons and then start considering it three and a half years before I did. And I am not saying that it was too long. I’m really grateful that I didn’t need to just jump into dating, but I think it would’ve been healthy to start a little bit earlier. I had one date and I’ve talked about it before, how awful that was. But anyway,

So I’m going to throw some statistics in here. I love numbers and they’re different depending on where you hear. But from a widower and widow perspective, I’ve heard that anywhere between 60 and 70% of widowers—so males who’ve lost their spouse—move on within the first year to 25 months. So they’re moving on quickly. Usually within the first year, they’re starting to date. Widows, on the other hand—women who have lost their spouse—are not even starting to date until two years and seven months. So those widowers are remarried before the widows are even starting to date. So there’s a wide gamut of what people are doing out there.

There’s something about the sooner you get married after divorce, the more likely you are to end up in a second divorce or a third divorce. The statistics get higher the sooner you get married again for a second or third time. Well, I think time could be our friend, and I think that’s why plugging into Solo Parent groups or whatever [is so important]. One of the things that we feel most alone in is that there’s no one else. There’s no sounding board. You used to share your life with someone. You could talk about everything. And that just evaporates. And so that’s why our groups are so important to have—other relationships that can meet some of those needs.

Do people start off casually dating before trying to find a long-term partner?

You did, right. I remember there being a point where you were like, “I am only dating to go have fun and to just go have some meals, meet people.” At first. When I first started dating again, I wanted to have fun. I still had boundaries in place, no doubt. But I was less rigorous in my screening process because I just wanted to see what it was like. Could I go out and have fun? What would it feel like? What would the experience be like? And so I was casual about it in that way. I’ve never been casual about my boundaries though, and I think that’s pretty important.

Everybody has a rebound, right? Why not just toss the rebound out with the bathwater, if you will, where it’s like, okay, casually date for a little bit and treat that as your rebound before you start. I hear what you’re saying. I think that it really is true that after you’ve been in a significant relationship, the first person you date again, almost never is going to be the one. And I did date someone for several months, and I actually really liked him, and I still kind of feel like he’s the one that got away. But he was my rebound person after my engagement broke off. And I thought I was ready to date 90 days later—I wasn’t. But I tried it and I learned something. I wasn’t quite ready. 

Well, it’s fascinating for me to hear you ladies talking about this, because I never thought about casually dating ever. I didn’t. After I got divorced, it was like I’m not in it for my own fun. It’s like either this is going somewhere or it’s not. And so I am fascinated by that. And I am not saying that I’m right and you’re wrong. I think you’re probably more right than I am. I think I was too uptight about it and why I took so long to date. And what’s interesting to me, Robert, is hearing you say that because you gave me the advice to have fun, and it’s been one of my key foundational things—surely this should be fun. If it’s not fun, what are we doing? 

For me, I was so strict about how I wasn’t going to date. I wasn’t going to date. And then there was a woman that rented a room from my family. It was not a romantic thing, but she was an older lady and she was such a beautiful soul. Her name was Nanette. And she lived with us for about a year and a half and I learned so much from her. She was just such a godsend. But she got cancer and she passed. But in hospice, I went to go and see her and I said, “Nan, I’m dating someone.” And it was Barb, my wife, and I was bummed. I knew Nan wasn’t going to meet her. And she got cognizant all of a sudden, and she looked at me, she goes, “Robert, just have fun.” And it was like almost this soft reprimand where she knew me well enough, she lived with me to see how I didn’t want to make a mistake. I don’t want to get this wrong. She was the one that gave me permission to go, “Just for crying out loud. Just have fun.” That’s why I passed it on to you because you and I are similar in the sense that you want to get things right. And I’d messed up so much in the dating world and in the marriage world that I’m questioning myself. So yeah, I do think fun is an element.

So I mean, I don’t do casual. I did go meet people for a conversation. I was like, “Oh, whatever a meeting, unless they’re sketchy, doesn’t cost me anything.” But I was very quick to be like, “No, this is not going to be a long-term something. I’m not wasting your time and I’m not wasting my time. I saved casual for all of my other relationships, I guess. So you have to just

decide for you what you want and where you are with the timing of it all. Yeah, I think it is very unique.

So next question, and this is a big one. Could take a couple hours here. What are all the rules? And this is asking for somebody who hasn’t dated since being a teenager.

Gracious, I think we just touched on it, which is that I think it really is, and I might sound like a broken record today, but I think it’s really unique to your individual situation. I think the rules may need to be general and you need to be safe. You need to be relatively healthy. I think you need to be thoughtful. You need to have some external guidance, not just go in it alone. Those are the kind of bigger principles that I tend to think of. Are those rules? I don’t know.

I’ll add to that. I think it’s more about there are no right or wrong rules per se, but do not attempt dating unless you understand what your values are. Like these are the boundaries, these are whatever. And it doesn’t have to be everything you’re looking for, but I am willing to do this. I’m not willing to do this. I’m willing to emotionally go deep or not, or physically, where am I at? Where are my boundaries? So I think it’s more important to have an internal inventory of rules rather than going, I’m going to enforce this; these are the rules for dating in general. It’s more about internal stuff.

So I’m going to throw out two that I’ve picked up from my teenage boys. One is there is a phase called unquote talking, which maybe that’s obvious to everybody. And I would get into this situation where you meet somebody, you go on a couple dates with them, and what are you, at what point do you become, “I’m dating.” But there is this thing called talking, and you could talk forever, but there’s also this respect level of my children will say, “Oh no, she’s talking to somebody, so I can’t ask her out.” So I’m not completely sure about those dynamics. Maybe sometime we’ll have to get somebody who’s much younger than I am to talk about what talking is. I think for me, when I was in the dating scene, it is helpful to say just because you go on a couple dates with somebody does not mean that they’re your boyfriend or girlfriend. So there is a line where you’re probably going to have to say, “Hey, are we a thing now?” So just prepare for that, prepare to be not a thing, and then have some really awkward conversation where you put yourself out there and vulnerably ask if we were a thing. I very specifically remember having that conversation in my last relationship at the beginning, after it was probably a couple of months, and I was like, “So are we doing this? Are we a thing?” He was like, “Yep, we’re exclusive.” 

So another one, don’t leave people unread. So apparently with texts, people don’t want to just have you read the text and not respond. In my busy life, that’s impossible. So I’m going to have to be dating somebody who gets that. You might be left unread even overnight. The third one, and it’s not necessarily something my kids are talking about, but if you’re going to date, you’re also going to break up or you’re also going to have to tell somebody, “I don’t want to talk to you anymore. This isn’t working for me.” So colloquially people will say, “Don’t ever do that on text.” If I went to coffee with you once and the rest of our relationship has all been on text, I’m breaking up with you in text. I’m sorry. And I’m probably having my child write it.” True confession I did because I was like, “How do I make this sound nice?” If I’ve been to your parents’ house, I know your children—do not break up with that person on text, do it. But where your relationship is. So if you’re having nightly phone calls, then maybe it’s a nightly phone call where you need to tell a man, “This is just not working for me.” But you do have to know how to break up and be willing to have some awkward conversations if you’re going to start dating.

Let’s say that Amber, we’ve gone on a couple of dates and [they say], “I’m way into you,” and you’re just having a good time, but you’re not quite there. And I know you’ve experienced some of this. How do you have a conversation where you don’t want to just shut it down completely, but you just have to be honest with, “Look, I think that cart’s a little bit ahead of the horse.” How do you have that conversation?”

Men fall in love with you quickly, Amber. Yeah, that’s hilarious. It’s kind of true. It’s really awkward conversations that you end up having to have. And it’s one of the things that gets me burned out on the dating roller coaster is that at the bottom of the hill, someone’s going to be disappointed, and either I’m delivering the news or I’m receiving the news. Right? Honestly is how I would have that conversation. “Hey, it’s so sweet that you’re so interested. I’m really flattered and I enjoy your time. I don’t know where this is going yet. I think I need more time.” If I were to sum up my dating process, it would be that way: Honestly. How do I approach this honestly, with kindness for me and kindness for them? What I like about that is that it really is about releasing control. You’re not trying to take control of it, and you’re not allowing them to take control of it. You’re just going, “This is just where I’m at. I just have to live into this.”

So what is the correct mentality for the first and second dates? In other words, should we be expecting a spark on the first date? 

I feel like you can probably tell on the first date, if you want to have a second date. I can usually tell on the first date if I want to have a second date. And I’m going to tell you, it only goes down from there. So you better be bringing your A game on your first date, right? Not to put pressure on the person going on the date, but if I don’t feel something or if the conversation’s off or whatever, how do you think it’s going to go from there? And now granted, sometimes people get awkward and weird or nervous on first dates, and maybe you have grace for that and that’s fine, and you want to try a second date to just see and open up your mind and the possibility of it. But I don’t know. I’m more of an intuition person, so my gut would tell me whether or not it’s going well. I would say that the online dating scene makes this a little bit awkward and more difficult because in the old days, you’d see that guy at church, maybe he would answer questions in Sunday school and you’d be like, “Oh, I like the way he thinks.” Or you’d talk to him at several parties, you’d observe them, and then it’d be like, “Well, he’s interested in me.” Now it’s like, a complete stranger from nowhere. I may not have a spark the first time, but to Elizabeth’s point, I may have the intuition that I’m never going to have a spark with you because I just can’t do this. Our conversation’s not interesting enough, whatever the reason is. I mean, I refuse to go out with people a second time for very stupid reasons.

Well, before you even go on a date, have a good 30 minute conversation on the phone, no texting, none of that. Get on the phone and have a conversation and feel out the dynamics, see if it works. There was a guy that Marissa and I both know that I got set up with by a different friend, and she gave him my number. He called, we had a 30 minute conversation, and it seemed fine. And we had been texting a little bit, so we had some things to talk about, and it seemed like he liked some of the same things I did, whatever. And then anyway, we ended up at the park for a lunch date. The most boring human I’ve ever met in my life. Well, there’s that. And that was it. It was like, “I think I’m good.” But to add to the story, you then told me later at a party that you had met him, I was like, “Why would somebody hook you up with him? No, he’s great for some people, but not Elizabeth.” I can totally see that. To be fair, the friend who connected me didn’t know me very well at the time. I think today she would’ve been like, “Oh, that was dumb. Don’t do that.” 

So how do I jump back into dating safely?

One of my best friends uses dating apps. She’s been catfished. Not to instill fear in anyone, but the dating apps are crazy, right? I mean, you just don’t know what you’re going to get. It’s wise to be cautious, no doubt. And so I would just say tiptoe into the dating app world. She actually has a practice of when she is talking to someone, she actually has them take a real-time picture with their id and show their face and driver’s license in the same picture. And that’s how she’s caught people catfishing and being scammers and all that.

And so all that to say, I think there’s some wisdom in safety. So I’m thinking about physical safety. I’m thinking about dating app safety. Also, you don’t know what people’s intentions are, because I’ve seen multiple times women saying, “This guy told me he was a godly man, told me that he goes to church, he wants a family, he wants a long-term relationship. And then when I told him I wouldn’t sleep with him, he ghosted me.” So know your worth, your boundaries. Know who you are, know what you’re wanting, what you’re looking for, and if it’s casual, that’s fine, but have your boundaries in place, all those things so that you can protect yourself because nobody in the dating world is protecting you. You’re the one that’s got to protect you.

And I would say nobody needs to pick you up for a first date. You need your own car. You need an exit strategy. People need to know where you are. All of the things. Share your location with a friend. And a guy friend recently said to me, “Amber, do you wait for them to leave the parking lot before you do so that they don’t follow you home?” I was like, “What?” And he said, “Wait for them to go. Don’t leave the parking lot first because they could possibly follow you home.” Can I also say though, as a guy, if I was out on a date with someone, I would not leave first. I would want to make sure that they left first. So maybe then go to a Walgreens or make a stop along the way. And there’s this huge resistance inside of me because I have to be honest, if I am having to be that cautious, I don’t even need to go on that date. That’s how I feel. So I haven’t always had to have these really strict safety parameters because I don’t feel safe enough to go on a first meeting with you … do you hear what I’m saying? So at the same time, I think using every caution possible is needed. It’s crazy out there. 

How do you meet people?

I’ve never been on a dating app. I’ve said it multiple times. And now that I’m single again, I don’t know that I ever will, honestly, I don’t really care about that. I can’t even think about it. But I mean, organically getting out there, I feel like my friend, who I was saying, who’s on the dating apps, we’ve been getting onto her. There’s three of us that are best friends. We’ve been getting onto her because she only sits in her house all day, every day. And then she swipes through the dating apps, and she’s wondering why nothing’s happening. And the thing is, her charm, her charisma, her light that she shines out to the world can only be captured in person. She’s one of the funniest people I’ve ever met. She brings a lot to a relationship, friendship or otherwise, but sometimes that can’t be communicated through an app. And so we’ve encouraged her to go to there’s singles networking groups or singles dating events. There’s speed dating, there’s all kinds of things, obviously this being if you live near a larger city, but there’s all kinds of opportunities that you can get out into the public and do that.

How do you meet godly singles if they’re not in your church? 

I think with the church thing, it’s hard to do that unless you’re in a Sunday school group or in a small group or in something like that [because] you don’t want to just be going to a big service scoping out the singles. You know what? That’s creepy. 

I will say that I did not think that meeting in person was an option for me. I didn’t, I wasn’t anywhere. So maybe just be specific to my profession,

But in the music business, it’s such a small circle. I felt like I knew everybody. I didn’t really network beyond that. It was just kind of all enclosed. So the only way to meet other people was to step into an online thing, which was so uncomfortable. But I think it really depends on where you’re at with things. I didn’t want to use the church. And my friend Nate, who forced me to start dating again, basically said, “Just put yourself out there. Go on eHarmony.” But I don’t think I would’ve, because I told him, I go, “Where am I going to meet someone? I don’t go to bars and hang out.” I had a hundred percent custody all the time. I had no time. I had nowhere to go to meet anyone. And so sometimes it is the easiest option, and sometimes it is an effective option. I mean, I met my wife through an online dating thing. So I think it just depends on where you are.

How many people can actually meet somebody online? And if you are going that route, what do you put in your dating profile? Is it worth it to do online dating? Are there people that you’re finding there that are worth spending time with? And 

Well, I mean, I’ve been married for 10 years, so this is a while ago. I used eHarmony, and it was very uncomfortable to put myself out there. But the practice of eHarmony, at least at the time, was you have to fill out all these things and they match you with potential matches, and you get to choose from people that they think would be in the same kind of realm as you. So there was some of that stuff that people could have lied, obviously. It was helpful to have that guidance along the way, but it was very uncomfortable. I think one of the most uncomfortable things was once I started talking to someone, my wife, I eventually had to meet her—which is very odd. Within eHarmony, they facilitate the questions, they control the tempo and all that. And so then it’s time to give this person a call. I mean, they didn’t say that, but that was the next step. And I remember the first time I heard her voice, we’d only been digital, and that was weird. And then the first time seeing her was super weird. I knew a lot about her prior to ever meeting her in person. The whole thing was very weird. But it worked for me, and I’m grateful for it because I never would’ve met her. She’s a nurse. She’s completely outside the circles of people that I would associate with. Not as any kind of prejudice. So it opens up a realm of possibility there. And I know other people that have gotten married because of meeting someone online. So I know that it works, but it’s got its own challenges. 

When I first thought about online dating, I was resistant and thought, “No, this isn’t for me.” But now that I’ve been part of it, I really see a lot of benefits. I don’t view it as very scary or even intimidating. I actually think it’s beneficial in many ways because very quickly I can get a snapshot of certain qualities, values, and core beliefs or lifestyle choices that may or may not align with me. And I don’t want to sound too creepy about it, but it’s sort of catalog shopping, like, Nope, nope, nope. Oh, that kind of fits. And I actually think it’s helpful. You have a little bit of a resume on someone before you meet them. That’s more than I would have if I was in a big gathering or in a huge social event. I’m like, “Well, he actually has children under six. That’s not a good fit for me. I’m an empty nester.” And you wouldn’t have known that if you just met someone at a potluck or something. And so in some ways it’s really helped me to filter and narrow in on the things that are most important to me. And hopefully it’s doing the same in reverse to people who might be online looking as well. 

What do you put on a dating profile? 

I’m just totally outing myself here. But I thought it might be helpful to some of our solos. So I screenshotted it and I’m going to read it. This is just one of them because I’ve tried a few different dating apps. I’m just sharing it all today. “Okay, so hi. First and foremost, I’m a Christian. I have two kids I treasure, 20 and 22. They’re a big part of my story as is my faith, which I want to share with my partner. I love my family, friends, and the beautiful life God’s given me. I like to hike, kayak, explore new places and try new things. I enjoy Nashville’s arts and music scene and local events too. Are you ready to go with me? I’m looking for someone intelligent, kind, cute, and fun who’s local for genuine connection. Great conversations and laughter.” And I admit it’s a little awkward to share that with you all here in the studio, and also with our solo parents. But I think it’s important to be authentic. What is the most important thing about me? That I love Jesus. So I wanted to offer that.

How do I spot the red flags? When someone is pretending to be something they are not, and friends or family do not mention their concerns?

I have a phrase I use: Listen with your eyes. People can say a lot of things. They can tell us a lot of things. They can put a lot of words out there, but it’s really difficult to show me someone different. So I guess it’s two things. Go slow, watch and see who someone is. Don’t just believe what they’re saying or writing or presenting. Listen with your eyes for a long enough time to really see who they are. Amber, you went on a date with a gentleman. You were sitting at a bar waiting for your table at the restaurant. He made several very inappropriate comments and that caused you to say, “You know what? I think I’m good here. It kind of shows me who you are. It’s your heart, no doubt.” Because his resume, whatever he said online, added up: He was a Christian, he was professional and seemed solid and stable, but his behavior in person really wasn’t aligning with the character that I’m looking for. [He had] some derogatory remarks about people that were just unkind. So be super observant. Don’t just trust what they put out there. Don’t put your rose colored glasses on like I do, and not see things for reality and what they are. And I think one component of that is watch how they treat other people. Sometimes that’s easier to see. They may make you feel great, but if they’re making the person next to you feel like dirt, whether that’s the waitress or whoever, then that’s how they will make you feel eventually. 

Let’s get through a few of the differences we’re looking for. So this person wants guidance on interpreting the difference between not interested and playing hard to get and being romantic versus creepy. So the difference between not interested in playing hard to get—I say if they’re playing games, “Bye.” Just don’t play games. And if there are games being played, you’ve got better things to do. And I would say, trust your gut and ask friends like, “Hey, this is what’s going on. Put me in my place here if I just need to be more patient.” Or you can even ask them and be straight up and say, “This is what I’m looking for. Is it what you’re looking for?” Ask the question too. 

Romantic versus creepy. I had someone do some romantic, romantic things for me at one point, and I definitely took ’em as creepy because I felt like it was overboard. I’m going to ask from a guy’s perspective, because this is one that guys will get stuck on. You want to show romantic interest, but you don’t want to come off creepy. So what is received as romantic versus what is creepy?

I got pages and pages and pages of letters sent to my house to someone I’d never shared my address with. That’s creepy. That crosses a line. Anything that crosses a boundary, they encroach in your personal space. They lean in for physical contact and you’re like, “Hey, my body language didn’t say that. That’s creepy.” When they encroach on your personal boundary of your location or your house, that’s definitely creepy. Showing up at work. A guy that I had texted a few times, never met this person, never talked on the phone, said to me, “Hey, I’m thinking about sending you flowers for Valentine’s Day. Would you like that or would that be creepy?” I was like, “Is that even a question? To your point, I’m not going to give my address away for you to have flowers sent to me. We’ve never met. 

When do you introduce your kids to a new or potential person?

I know in my last relationship, we waited four or five months, and this was all him. I had never had a lot of experience with this, and so this was all his doing. But he introduced me to his kids separately from Jax—he was not involved, and then I introduced him to Jax. And we did that a few times each before introducing the kids to one another. So that was kind of the way we did it. I say the longer the better with the kids’ situation. If your kids are younger, especially. And here’s the thing, it’s tempting sometimes, especially if you’re excited about the person you’re dating. You love your kids and they’re everything, and you’re like, you want to share something that’s exciting with them, but just be super careful about it. I don’t think you can wait too long. Amber, you’re looking like you may not agree with that. Well, I completely agree with that. With younger kids. My kids are 20 and 22, and this past year I dated someone and they met him within, we had probably been out four or five times. And their insight is valuable. And I actually want them to know my intentional dating process. So I wanted them to be part of it. I didn’t want them to be worried or afraid about who I might be dating. I wanted them to see these are solid guys who love God, who love me. And I always try to make that so clear to them how safe the people are that I date and how intentional I am in this selection. I think it varies by age. 

How do you go about tackling and introducing and answering all their questions? My curious 9-year-old asked if I was still his mom when his dad brought someone around. How do you introduce them and how do you answer those questions?

Yeah. Well, truthfully, yeah, exactly. I was going to go back to that earlier point. I’d answer honestly. And with kindness and respect and age appropriately, “No, that person your dad is dating is not your mom. I’m your mom. That’s never going to change.” And if they’re wondering about something about my dating life, age appropriate. 

Do you tell or introduce your new person to the ex?
I told [my ex] strategically several weeks before I was going to be introducing [Jax] so that he had time to deal with his own feelings because I knew that it could trickle down to Jax. And I didn’t want the information coming from [him], I was trying to probably in my codependency too much, but I was just trying to keep Jax safe more than anything with it. And then they naturally met over time at church or school events or sporting events or whatever. 

So kind of moving on to another big topic is that long distance. 

I would say for me, I wasn’t willing to uproot my kids, so I knew this wasn’t going to work out. No way I’m coming to you and I’m not going to require that of somebody that I love because I’m not willing to move. So for me, that was a non-negotiable, but I’m sure other people have other opinions on it. Yeah, look, anything can work if you want it to work. It’s just you have to understand, “What are my values? What am I willing to do?” Sometimes moving might be a good idea. It might be a fresh start, but for me personally, that was just a non-starter because you’re not just moving, your kids are moving. And so too are the dynamics of sharing custody. 

So we have a couple of questions here about doing the work and healing, also dealing with your trauma and struggles triggered by difficult past relationships. 

Amber and I were talking about this at dinner last night about how it’s natural that you’re going to learn what those triggers are [while dating] because a lot of times you don’t even know. I wasn’t aware of my triggers until I got into a relationship and saw it come face to face and learned how to navigate those. And so I think it’s being able to know your value, but then even having done the work, one of the things that I want to do, I’ve made that list a list of my value and my values and all of that. I also want to start taking inventory of my triggers. What are the triggers that I’m aware of, that I know of, so that I can at least just be aware of them so that if they come up, I can have an outside perspective to be able to say, “Oh, that’s triggering me. And here’s how I’m going to handle it.” But it takes some awareness there more than anything. And then being in it obviously and learning through the process. I’ve learned a lot through dating and I think it can be really refining and an opportunity for self-awareness. I know a lot more about myself, what I like, what I don’t like, what I want, what I don’t want, how I respond to certain things—that I would never have learned just sitting on my couch alone at night. And so I think it’s a very valuable process.

How hard is the first real breakup? And I’m taking this one because here we are. Is there any advice to make it easier? 

No. It’s just hard. It’s painful. It absolutely is. And there’s no getting around it. There’s no taking the pain away. And every moment, every hour is different. Every day is different. Today I woke up with such an intense feeling of missing him. I cannot even describe how much. This whole week I’ve been missing him so bad. I prayed, I journaled, I did all my things, took care of myself. [And] today, this afternoon, I still miss him, but I’m okay. I realized that I’ve got enough people around me, I’ve got ways to fill those voids and those holes. I’m strong enough to sit in the pain of it and it’s not going to last forever. And so you’ve just got to go through it, as bad and as sad as it is.

I’m sorry that you’re facing that, but I think that is part of it. Dating again is a risk. And anytime you’re walking into a risk, you have to evaluate that there is a possibility you’re going to get hurt. And just like anything, what you’re doing right now as a single parent is risky. You’re not going to get it all right all the time. And there’s going to be hard days and there’s going to be less hard days. There’s going to be days that you feel so connected to God and others and to your kids. And then there’s days that you’re going to feel completely isolated and alone. But in all of it, it’s risky. Putting your heart out there again is risky and making yourself vulnerable is risky. And so it’s important to count the cost, but at the end of the day, just knowing who you are, whose you are, and having the support community around you will enable you to take those steps. Don’t try to do it alone and certainly bring other people into the dating relationship relative to “What do you think of this person? Or when you see me and this person together, am I different?” Things like that. Bring others into the conversations.

Listener Question: What’s something you’ve done for yourself recently that’s helped you recharge or feel more balanced?

I really like this question because for Christmas I received watercolor supplies to paint. And being creative has been an incredible way for me to be recharged and to feel more balanced. It puts me into a totally different part of my brain. I have to go into the flow of art and creativity, and it shuts down a lot of my overthinking and overanalyzing, which I can get really stuck in. And when you’re busy creating with your hands, guess what you can’t be doing? Scrolling your phone. Or ruminating on, right? That’s right. It’s both. And so it’s been incredibly restorative and just such a place of relaxation. And so if you have a creative opportunity, try it. 

Cooking was that for me. It’s the same thing. It’s creative and there’s a beginning and an end. It’s a tangible end product.

I kind of want to go get a watercolor kit now. Anyone who knows me knows that I train for races. And so I’ve been doing a lot of running and Amber invited me to a yoga class that’s coming up, which is exciting. And yesterday I went to my very first Zumba class which was fun. 

So this is kind of a nerdy thing, but I spent all day in numbers. And so I actually went on a different retreat and it was kind of creative, I wasn’t working in numbers. I was planning the launch of a different business. And to me that was fun because I wasn’t just thinking about numbers. So it was a very, very nerdy answer. But as I walked away from it, I was like, “Why do I feel so much better? I literally worked myself to death here.” But it was just a different part of my brain and I got a recharge out of it. And I was also with a lot of other people doing it, so it was a group activity instead of my day job which is a lot of silos.

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