Step by Step Parenting

Co-Authored with Kevin Allen

When I separated from my ex-husband in November 2022, I was almost twenty-three years old, had a two year old daughter, hadn’t yet graduated college, and had my whole life ahead of me. I had gotten married at only nineteen, so I knew when the time came, I would want to start dating again. Although I had suspected that my dating experience would be different than before I got married, nothing could have really prepared me for what it was like.

Similarly, when my fiancé and his ex-wife divorced, he became single for the first time in over a decade. After spending all of his twenties working towards someone else’s dreams, he felt like he was back at square one in life. That, and being the father of two young kids, made for an interesting debut to the dating scene.

Luckily, we happened to find each other, and we clicked instantly. In fact, we had already been good friends for almost a year. Finding a partner post-divorce is not the end of dating woes, however, but sadly just the beginning. It can be a rollercoaster of emotions, and it often involves a balancing act of your own feelings, others’ opinions, the wellbeing of your kids, and more. Although we are no experts, I had Kevin co-author this with me so we could whittle it down to the six hardest truths of dating post-divorce, particularly when both partners have kids from previous marriages. We wish someone had sat us down and told us all of these earlier, so hopefully this post falls into the lap of someone else who might need it! At the very least, I hope this post provides some insight for those in my life who haven’t experienced this.

1. People Will Judge You for Dating Again

Personally, I only waited a few months after my separation before I started dating again. While I wasn’t looking for a serious relationship, I also wasn’t opposed to some casual, fun dates. There were some people in my life that had things to say about this, and they weren’t exactly kind. But what they didn’t know is that my ex-husband and I first seriously discussed divorce for the first time over a year before we started the separation process. By time the divorce actually happened, I had been through months of processing and healing, and was ready to move on with my life. I had already lost the last of my teens and some of my early twenties to a failed marriage. The last thing I wanted was for it to consume any more of my life. I had to find a way to move on, if not for me, then for my daughter.

Beyond that, everyone heals on their own timeline. Some people might feel ready to date immediately, some might take a few months, and others might take a year or more. What works for one person doesn’t work for someone else. Just because your friend waited six months, doesn’t mean someone else should, and vice versa. Unfortunately, whether you wait two months or two years to date, people will say the same thing:

“I can’t believe she only waited [insert time here] before moving on!” or “It’s only been [insert time here] and he’s already dating again!“

The bottom line is you have to trust that you know yourself well enough to make the decisions that are best for you. If you try and wait for the “right time” in order to make other people happy and avoid judgment, you will be single forever. Furthermore, if you start giving too much weight to other people’s opinions early on in your post-divorce dating life, you’re in for a bumpy ride.

That being said, it is important to take the time to heal from your divorce, whatever that looks like. This might happen before the divorce, during the divorce, after the divorce, or all of the above, but it has to happen. For me, I started running, got a new job, and surrounded myself with an amazing support system. I knew I was ready because for the first time in years, I felt like myself again. Kevin, on the other hand, will say that he wishes he had taken a little more time to heal and work on himself before dating. Remember, it’s not fair to you, or anyone else you might date, to enter the dating pool before you’re ready. But on the flip side, healing isn’t linear and it’s ok to still be figuring some things out while dating. You do not need to wait until you’re 100% ready to go, but taking some time to consciously decide to move forward goes a long way.

2. There Is a Double Standard (and sometimes it’s in your head)

If any of my friends who are my age go out on a date, no one bats an eye, because most of them are in their young twenties with no kids. But when I started going on dates, I encountered a bit of a double standard.

I got asked things like “Where is your kid?” and “Who’s babysitting for you?” and “Why are you choosing to spend time on a date instead of with your kid?”

Questions like these honestly made me want to pull my hair out! My current custody arrangement has my daughter with me Sunday through Wednesday, and with her dad Thursday through Sunday. So when I was “choosing to date over spending time with my kid,” my daughter was actually at her dad’s house. It was annoying to feel like I was under more scrutiny than other people my age who seemed to have more freedom. It was exhausting to constantly try and play the guessing game of what people would judge me for next.

But to some extent, I think the fear of the double standard lived entirely in my head. Yes, there were a few people that seemed to think I wasn’t a good mother for going on dates, but (1) those people never bothered to ask me about my personal life (and if they had, they would have learned that I’ve never needed a babysitter to go on a date) and (2) those people are far outnumbered by the people in my life who don’t care, don’t judge, and just want to see me happy. A lot of my fear of judgment, or the feeling that there was a double standard, came from my own internalization of societal norms and expectations. Part of learning to date after divorce is learning to tune out what others think, and to stop wasting time wondering what others think of you at all.

3. Your Exes Will Always Be in the Picture

There’s no way around it: you can’t pretend that your previous relationship never happened. This is different from relationships in high school or college, where once it’s done, you can just forget about it and move on. Now, especially because kids are involved, even though you get divorced because you don’t want to be married to that person anymore, they are still going to be in your life forever. Every decision regarding my daughter is a joint decision between me and my ex-husband. Neither me or my fiancé can just decide to take the kids on a vacation, switch where they go to school, or buy them a cellphone (at least, we shouldn’t), because those are examples of decisions that involve and affect the other parent. It can be a sore spot for awhile, but part of dating after a divorce is both parties accepting that there will be some involvement from the ex. Remember that your ex isn’t with their ex anymore for a reason, and in a healthy relationship, you have nothing to worry about. It’s crucial to learn how to be the bigger person and be okay with their existence, because otherwise you are setting yourself up for constant mental and emotional exhaustion.

But beyond co-parenting and kids, this ex was a huge part of your life for however long you were together. They played a hand in shaping how you are as a person, and how you function in a relationship. Sometimes yes, that will mean that there are things you need to unlearn or heal from because of damage from the past relationship, but that work can’t be done if you pretend the ex doesn’t exist or impact you at all.

4. Dating Is Infinitely More Complicated with Kids Involved

There are three kids between my fiancé and I, which has definitely led to some complications. It also leads to lots of big decisions and tough conversations, such as when to introduce the kids to your partner, when to introduce the kids to each other, how to break the news to the respective co-parents (since your dating life affects their child), and how much or how little to involve the kids in your partner’s life. This doesn’t even touch on how difficult it is to move past the dating phase when you have kids, which is a topic so complicated and sticky, we gave it its own point below.

Kevin and I opted to have the kids meet via a neutral playdate at a children’s museum, and we just told them that they were going to meet new friends. Since the kids were all young when they met — K was six and T and my daughter were both two — they didn’t really question this. And they had a blast! My daughter loved having a girl to play with (Kevin’s oldest), and his youngest is only a few months younger than my daughter, so they’ve been like little twins since they met. On the one hand, we’re glad we introduced the kids to each other earlier on, just a few months in, since now none of them will really remember not knowing each other. For the longest time, they just viewed each other as friends, so we figured no harm, no foul. But on the other hand, there are a few reasons we wish that we had waited maybe a few more months. However, the older they would have been, the more questions and resistance there might have been, so really at the end of the day, it’s impossible to pick the “best” time.

When and how to introduce kids is just the beginning. Once the kids are involved, even if they are oblivious to the reality of the situation, you have officially involved their other parent in your own relationship, as well. Then there’s the fact that since the kids already exist and were raised at least partially apart, you and your partner likely have different parenting styles. This is true in any relationship, but for many people, a lot of those discussions happen during the pregnancy as part of the preparation for when the baby comes. Those conversations don’t happen until after the fact for couples that are dating after divorce, which can naturally lead to some dissonance. My fiancé and I have different approaches to a lot of things. I like to encourage my daughter to be very independent, whereas he likes to be more hands-on with his kids. He enjoys a thorough bedtime routine, whereas I like to read one book and call it a night. I have a tendency to be more strict with things like screen time and what goes on their dinner plate, wheres Kevin can be more lenient with things. Neither of our approaches are wrong, and they actually balance each other out very nicely, but it’s still an adjustment. Above all else, it’s been key to remember that almost every couple will have differing opinions on parenting, and although disagreements of any sort feel a little more scary and vulnerable post-divorce, they are totally normal.

5. It’s Very Hard to Move the Relationship Past the Dating Phase

I alluded to this above, but moving the relationship beyond dating is very, very difficult, and has probably been the most difficult part of dating after a divorce for both of us. There are two main obstacles that stand in the way: a mental block and logistics.

Mentally, it can be scary to face commitment again. Even though Kevin and I dated for over a year and a half before getting engaged and are otherwise head over heels for each other, the thought of committing to someone for life again, when you’ve already made that promise to someone else who it didn’t work out with, is terrifying.

For me, it was hard to both hear and say things like, “I want to spend the rest of my life with you,” or “I think what we have is special,” or even just, “I am so in love with you,” because in the back of my head was a voice saying, “You’ve both already said all of those things before, and it obviously wasn’t true!” This kind of thinking is very reductive and gets you nowhere. It would be the same as saying, “Well when I was ten, my favorite ice cream flavor was vanilla, so if I’ve said anything since, it must be a lie.” Back then, I truly loved vanilla ice cream, but as I grew and experienced more, I discovered peppermint ice cream, which became my favorite. Just because I loved vanilla once doesn’t mean I wasn’t sincere at the time—it simply means people change, grow, and discover new things. I don’t think Kevin or I would say that we never loved our previous spouses; we said those things to them and got married in the first place because we truly meant it. But we were young, people change, life and marriage are hard, and people can grow apart.

When you’re considering moving beyond dating after divorce, scary ‘what-ifs’ might lurk in your subconscious. But it’s important to remember that just because the previous relationship didn’t work out, doesn’t mean this one won’t either.

Beyond the emotional hurdles of committing again, there are practical considerations that can feel just as daunting, especially when children are involved. Logistically, it can be hard to move from dating to something more without feeling like you’re fast-forwarding to what is normally year ten of other relationships. It can feel like jumping into the middle of a novel without reading the beginning. In an ideal world, you meet someone, fall in love, get engaged, get married, move in, have kids, the end. Maybe a few of those are in a different order, like you start dating someone, have a kid, then move in, or maybe you move in before getting engaged, or something else. You don’t however, normally date someone, decide you want to spend your life with that person, then wake up one day with three kids. Moving in together means moving the kids in together as well, and that is a huge step to take. Whether it’s done before or after getting engaged, just the seriousness of it can feel intimidating. In our situation, the kids didn’t particularly mind; they viewed every night as a sleepover and every day as a playdate. But as parents, the severity of the decision can weigh heavily on your heart and mind. If you have any unaddressed “what-if” worries about being in another serious relationship post-divorce, those worries will get a lot more intense once you move beyond dating. Although the kids might not care because to them it’s just “fun,” it’s your job as a parent to protect them and put them first. When you’ve already watched your kid(s) experience a divorce, exposing them to another relationship can feel risky, no matter how secure and healthy that relationship might be. All of these concerns and more make the decision to move beyond dating that much more complicated, difficult, and even scary.

It’s been crucial for us to remember that while making that “jump” might seem like this huge, impossible task, plenty of families make it to the other side of that okay. You might find blended family horror stories if you look for them, but many families navigate these challenges and find happiness on the other side, so there is hope! It just takes a little more soul-searching, honesty, and work.

6. There Is No Template and You Know What’s Best For You

At the end of the day, no one knows your unique situation as well as you do. Every single divorce, every individual, and every couple are all different, so any advice (including this whole post!) should be taken with a grain of salt. I don’t know many divorced and remarried couples, and those I do know had very different experiences based on factors like their age, the time period (early 2000s vs. now), or the number and ages of their kids. I value their advice so much, but even they have acknowledged that every situation is just different and not comparable.

Beyond that, although there are plenty of online resources, from other blogs to websites to books, I quickly learned most of it was not applicable to our unique situation. And that’s okay! As with anything else, it’s important to be able to listen to other people’s experiences, put yourself in their shoes, validate what they went through, and apply what resonates to your own life.

Ultimately, trust yourself to know what’s best for you and your family—because no one else has lived your story. While these are what Kevin and I would consider the six most challenging aspects of dating after divorce, they aren’t roadblocks—they’re opportunities for growth. Each obstacle is an opportunity to deepen trust, understanding, and resilience. While the journey may not be easy, navigating these difficulties can lead to a partnership that is even more fulfilling and meaningful!

All photography is done by Kaylea Hardman Photography (find her here)