Should You Date or Marry Somebody Who Has Kids?

by Amy  - March 30, 2023

My story as a stepmom begins with a decision to date a man who already had 2 children.

Honestly, at the time, I didn’t even notice that I was making a decision that would impact the rest of my life. My thoughts at the time was that I was going to happy hour after work with friends.

That’s it.

Also true, is that this is the start of the story. This is a decision that I made that resulted in me becoming a stepmom.

I often meet my coaching clients at one of two points in their journey.

Either they are trying to decide whether to commit to making a relationship more serious or they have already committed to the relationship and it’s not going how they expected.

I think that it is a great idea to think about this early in the relationship. I didn’t do that. If you can I do think it’s a good idea.

These are some things that are a good idea (in my opinion) to consider.

I don’t know if you should date a man who has kids or not.

I want to be very upfront that I don’t actually know what you should do.

How could I? 

We’ve never met.  You are reading this in a blog post. I will share with you what I think might be helpful for you to know or think about if you are making this decision.

As a coach, it’s not my job to tell you what to do but to offer you tools and information and support while you make your own best decision.

One thing that is interesting about me as a relationship coach is that I don’t think our relationship status is a value judgment. You are worthy and wonderful outside of your family construct. Single, married, divorced, widow, stepparent. These do not reflect if you are a good or a bad person. Make the best decision for yourself. 🙂

In my story, he had been married, had 2 young kids and divorced before I even met him. 

I had never been married, had no kids and honestly at the time wasn’t planning on doing that in my future. I think that this topic is different if both people already have kids. In my case, I had no children.

You might have guessed but I changed my mind. I’m writing this close to 25 years after that first date.

I do not remember thinking about the seriousness of this decision until I told my mom I was going to marry this man and she responded with the question, “Are you should you want to take this on. It sounds like a lot.”

As I share this with you I just want to be up front that these are all things I have thought about in reflection. I share this looking in the rearview mirror of my life.

You can get my ten tips from 20 years as a stepparent by clicking here.

Things I enjoyed about dating my boyfriend who had kids.

You don’t often here people share the things they enjoy about this situation. So let’s start there.

Let’s start with what I thought was good and great about dating a man with kids. In my story, my husband is also older than me.

Dating an older man gave me a lifestyle that I thought was really fun. We got to do some really fun things together.

Dating a man with kids gave me a set schedule. I knew if he was available and when I had time off.

Dating a man with kids felt secure to me.

I knew he could hold a job and that he wanted a family because he already had these things. When you are in your 20s and dating other 20-year-olds you talk about do you want to get married and have kids. But you never really know if they are being honest with you. This man had already done these things … his answers were obvious. I also felt like I could see where his commitments were by how he treated his first wife and kids. This felt secure to me.

Now let me share with you what took me by surprise about dating and marrying a person with kids.

The kids got attached fast. We dated close to a year before I met my boyfriends kids. I don’t remember having any desire to rush this at all. My husband openly said that he only wanted to introduce me to them if we were pretty serious. I was not his first relationship after divorce and he said it was hard to explain break ups to the kids.

This obviously depends on the kids and their ages along with a lot of different factors. In my case almost as soon as they met me they assumed I would always be around and I was there to entertain and support them.

Our relationship got serious very quickly after I met the kids. I have spoken to other stepparents who have a similar experience. When we were dating before I knew the kids it was me and my life and then we had dates and experiences as a couple. When he had his kids he didn’t see me. I actually loved this portion of the relationship. It was fun. As soon as I knew the kids it was a whole different situation. Things got very serious very quickly.

The Instant Family. As soon as we moved in together I felt like my entire life and being revolved around the kids and their parents. Every day, every vacation, every meal, every holiday, every grocery trip went from being mine to ours. This includes their mom and the entire extended family. It was like jumping into a moving frieght train where everybody knows what’s happening except you.

Kids are very expensive. I happened to have pretty decent financial literacy when I started this relationship and it was important to me to understand my partners financial commitments. My parents suffered financially when they were divorced and I knew that I wanted to understand his financial position and what it might mean to me. Nonetheless, raising children and stepchildren is one expense after another for a very long time. It can feel overwhelming.

The first relationship and extended family is a part of my life. My husband’s commitment to his kids is forever. Every family and every parent will have their own experience with this but for me his children have a close relationship with their mom. This has meant that my husband’s first wife, her new husband, her new kids, her whole extended family have all been a part of my life and my marriage.

There is an open stigma attached to the role of stepparent or being a younger spouse. It was an unpleasant surprise that people had strong opinions about my relationship and what it meant about me and my partner. Sometimes people shared these with me directly which was always weird. Worse though was hearing it through the grapevine. Over the years people have called me a trophy wife. People have assumed I was a mistress and broke up his first marriage.

Grab my book, Blend! by Amy Stone

It’s had no examples of happy and successful relationships that looked like mine. I believe representation is important and the dominant message in the public about stepparenting is a pretty unhappy unpleasant story. This is a big part of why I do what I do.

There was a power imbalance in my relationship because I was stepping into an existing family. I didn’t realize this at first. The assumption was that things should continue as they were because that’s how they had been. My boyfriend/husband was used to getting the schedule from his ex. He wasn’t used to sharing it with me. Nobody was ready for me to have input … well most things. This is negotiable. Making that discovery was a key moment for me.

These were surprises. At various times I may have described them as “bad” but that’s not how I describe them here.

Why? Because in my opinion, every family and every relationship has challenges.

Dating and marriage don’t have to be permanent. One thing that I have learned is that buying a house and having kids are in some ways more permanent commitments than a date or a party together. That’s my opinion.

I don’t put any value or virtuous judgment on whether people are married or decide to stay married. In my case, over the years when things got hard I always decided that this was where I chose to be. That’s just my experience – when you make the decisions your choices may be different and there’s nothing wrong with that at all.

If you are curious about the changes I made in my life to go from flustered stepmom to happy stepmom I share those here.

Training for You

Grab my Steps for Happiness as a Stepparent

Lady Tremaine - A Look At The Wicked Stepmother Character in Popular Culture


Amy Stone (she/her/hers) is a life coach who helps adults in blended families. She is a mom, step-mom and a step-grandma. Other random fun facts include that She is a 7-time Ironman triathlon finisher and many many marathons and shorter races. She created

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