Dating Someone with a Kid in Your 20’s

Dating Someone with a Kid in Your 20’s

dating someone with a kid in your 20s text over picture of child playing with blocks

If you’re considering dating someone with a kid in your 20’s, be aware of all the obstacles ahead. Whether you’re entering a relationship with a single mom or a single dad, it’s important to ask yourself whether you’re ready for the limited one-on-one time, interactions with the ex and feelings of neglect.

In this post, I talk about my own story dating a single father, what to expect when dating a single dad (or mom), how to handle feelings of jealousy, and the importance of having a good support system. Not being their number one priority may be one of the cons of dating a single parent, but there are also a ton of positives that make it all worth it.

It’s a lengthy read, so feel free to skip to a certain section by clicking the links below:

My Story

In February of 2017, I started messaging back and forth with a match on Tinder named Chris. Our initial messages started out casual, but I remember one in particular that caught my attention right away. I had asked how his day was going and he had responded with:

‘Great! I took my son to gymnastics today and now we’re eating dinner.’

Woah. Hold up…SON!? I remember mentioning the message to my sister and her advising me to ghost him. I couldn’t though. Not only was he a really nice guy, but I also felt like that wasn’t fair to do to anyone before meeting them.

Soon after, Chris asked me out on a date. We met up at a Jazz bar across the street from where I lived and got to talking about our jobs. He told me how he worked at the Ford plant and gave me his standard follow up line of ‘it’s not too bad, I get to listen to audiobooks while I work’. I can’t remember the exact conversation we had about him having a son, but I know the topic was brought up. For me though, it wasn’t real yet.

Meeting the Child

We continued dating, and after a couple months, he asked if I’d like to meet his two-year-old son and the rest of his family. Since Chris lived at home, I would be seeing a lot of his family in the coming months.

The initial ‘meet and greet’ was a bit awkward for me. I felt like there was so much pressure for him to like me and vice-versa. I hadn’t had much interaction with kids his age before, and it was difficult for me to connect with someone that couldn’t really talk yet.

The best advice I can give to someone meeting their partner’s child for the first time is to not feel pressured to fall in love with them right away. On that same note, don’t come into it thinking they’ll like you right away. It takes time to build a relationship, and they didn’t choose you the way your partner did. Start small and work your way up.

it takes time to build a relationship, and they didn't choose you the way your partner did text

After the Honeymoon Phase

During the beginning stages of our relationship, Chris had to ask family members to babysit so he could take me out on dates. As our relationship progressed though, that got cut back to one night a week. It was still incredibly nice that his parents were willing to babysit for Chris on a weekly basis, but this is something that you should consider if you’re going to be dating someone with a child. I still have a great time with Chris when we’re playing with his son, and we still have alone time after he goes to bed. But a child (and especially a toddler) will affect how much one-on-one time you have with your partner. This may be an especially tricky situation for someone whose love language is quality time.

Bedtime and Co-Sleeping

Consider what time your partner tends to put their kid down to bed. If it’s 10pm, you’re going to be missing out on that alone time. And on that note, consider whether your partner co-sleeps with their child. I can never remember a point in my childhood when my parents let me sleep in the same bed as them, but every family is different.

If your partner co-sleeps with their child and it takes away from your alone time or sex life, be sure to communicate with them about how you’re feeling. Instead of attacking them, explain why you feel how you do and ask them to try and wean their child off co-sleeping. Maybe start by negotiating; Co-sleeping only on the weekends or special occasions. Be sure to set boundaries with what you’re comfortable with.

Sacrifice and Feelings of Jealousy

There were times where I felt like a third wheel when I was around my boyfriend and his son. And then I felt guilty and ridiculous for being jealous of a toddler. I misinterpreted my partner’s concern for their son as disregard toward me.

there were times I felt like a third wheel when I was around my boyfriend and his son text

I also felt like I was getting jipped out of the fairytale relationship that I had waited 21 years for. I saw how my friends were able to take weekend trips with their boyfriends and stay out late dancing. I didn’t understand why fate had dealt me this hand.

I felt pressured to love Chris’ son the way a biological parent would, since my father had adopted me when I was three and never treated me any different than his biological kids. My boyfriend was ready for an engagement, but I wanted to be sure that I loved Chris’ son before I committed to that. Some days I asked myself: What if I’m just not cut out for this? What if I’ll never love him the way he deserves?

It’s hard to admit when you’re struggling in this type of relationship, because you know that your partner is doing the best they can. BUT it’s important that you voice your concerns. After all, they’re a package deal. Communication is key in a healthy relationship, and your partner needs to know that you’re struggling. Understand that you’ll never love their child if you can’t overcome this jealousy and come to terms with the sacrifice required.

It’s important for your partner to know you’re struggling, so they can take action to fix the problem.  This might be in the form of making more time for you or lowering expectations. It’s a partnership, so don’t feel like you have to work through it on your own. 

Having a Support System

One way to help alleviate the stress is having a great support system that can empathize with your situation and help you transition into that parenting role. When I watched Chris’ son over Labor Day weekend, my parents, grandma and younger siblings were there to help. My family will often join us for lunch on Sundays, and we plan trips so we can all go together. My friends are always there to listen to my concerns and provide honest feedback.

For those that don’t have this support system, consider joining playdate groups to help work in adult interaction even when you’re babysitting. Try out MOPS if you come from a religious background or Tinkergarten if you’re adventurous.

Dating a Single Mother vs. a Single Father

Although I haven’t been able to find any research to back this up (please comment below if you find anything), I’ve heard from others that it’s more difficult for a woman to come into this type of relationship than it is for a man. Why could this be? Maybe because men feel like they need to fill that ‘savior’ role and women don’t have this same expectation. Or maybe it’s that women feel more competition with the biological mother since there’s already such a strong bond in place.

With the societal and internalized expectation of women to be naturally maternal and serve as the primary caregivers for children, it can be difficult to grapple with the fact that you’re not fulfilling that role. And on that same note, two women in similar roles are often placed in competition by others (ie: the wicked stepmother vs. angelic birth mother). I’ve seen the love my boyfriend’s son has for this mother and thought to myself: I can’t imagine he’ll ever love me that much.

Competing with the Biological Parent

Here’s what was wrong with my thinking. I was worried about how MUCH I was being loved instead of being satisfied with the fact that I was being loved at all. He may never love me as much as he loves his mother. But that doesn’t mean I can’t try and love him as much as I love my future biological children. Instead of trying to be better, focus on being the best you can be.

instead of trying to be better, focus on being the best you can be text


On that note, realize that dating someone with a kid in your 20’s will be vastly different depending on whether they co-parent or have full custody. Many may not be familiar with the term, but co-parenting is “a parenting relationship in which the two parents of a child are not romantically involved, but still assume joint responsibility for the upbringing of their child”. In these types of arrangements, both parents agree to put aside personal differences for the benefit of the child’s development. It involves a lot of communication and cooperation, so get used to hearing a lot about your partner’s previous relationship.

Oftentimes, a mediator is called in to help create the co-parenting plan. This plan outlines how costs will be split, scheduling, medical information, etc. Issues that your partner and their ex will have to agree on include discipline, decision-making, vaccinations, religious upbringing and much, much more. If you’re entering this type of situation, be prepared to deal with all the fun drama that comes with co-parenting.

Figuring out What the Child Should Call You

Deciding what the child should call you is really dependent on the situation. If the child already has a mother/father in the picture, don’t ask the child to call you ‘mom’ or ‘dad’ right from the get-go. Just don’t. It undermines the biological parent’s role and creates confusion for the child. For mine and Chris’ situation, we decided that his son should call me by my name.

One of my favorite memories is when Chris and I were checking out at Costco and his son told the cashier ‘this is my daddy, and this is my Gabby’. The cashier had responded with ‘no, that’s your mommy!’ There’s always going to be a little awkwardness when explaining that you’re not actually the mother/father when you’re all out in public together, but it’s important that you understand your role.

Titles may differ depending on the age of the child and whether you’re married, engaged or dating. Check with the actual parent before making the decision to label yourself ‘mom’ or ‘dad’ prior to a wedding.

How to Build a Relationship with the Child

Bridges don’t get built overnight. Creating a relationship with your partner’s child may take months. Heck, it might even take years. This can be dependent on the child’s age, whether they’ve been burned/abandoned in the past or how much effort you’re both putting in.

Though you may start out just seeing their child once a week, make an effort to increase this number as the relationship progresses. People who have children don’t tend to just ‘mess around’. They’re looking for commitment, and a future parent to their child. Show your partner that you’re invested in building a relationship with their child by getting them thoughtful gifts, spending quality time with them and offering words of encouragement. Basically, treat the child like you treat your partner. Bust out those love languages, even if it puts you in a vulnerable position. Establish yourself as a role model before you put on the parent shoes.

show your partner that you're invested in building a relationship with their child text

Sharing Responsibilities

One of the best ways to become comfortable in a parenting role is to share responsibilities with your partner. Instead of sitting on your phone while they get their child ready for bed, help them. Read the child a story before bed, get them buckled into their car seat or work on getting them to eat their dinner. Sitting by the wayside will make you feel like an outsider and fuel feelings of neglect. When you and your partner are working towards the same goal (ie: getting their kid into bed before 9), you’ll feel more like part of the team.  

The child will also come to see you more as a parent if you’re taking on responsibilities. Where this can become tricky is with discipline, especially if you and your partner have different approaches.

To Discipline or Not to Discipline

Even if you don’t have a child yourself, you still probably have opinions on how children should be disciplined. Spanking was normal in my household, though it was only used as a last resort when talking and a time out didn’t do the trick. As toddlers, a slap on the hand was more common.

Chris, on the other hand, had pretty hands-off discipline growing up. He was never spanked, and it isn’t a discipline tactic he wants to have with his son. Instead, he likes to take the ‘talk it out’ approach. He’s much more hesitant to use phrases like ‘no’ and takes the time to explain why his son can’t do something. He negotiates and makes deals, counts to 3, and only uses time outs as a last resort.

I’m a much less patient person. It’s harder for me to sit there and have a twenty-minute conversation about why he has to eat his dinner rather than just laying down the law. However, I’ve seen that Chris’ tactics work—his son rarely has tantrums. Even if it takes longer to get to the desired result, it get the job done.

Discipline should be dependent on the temperament of the child and psychological concerns that may be at play (ie: ADHD). Defer to your partner’s tactics if you’re in a situation where you have to be the disciplinarian. And be open to different ways of discipling than the ones you grew up with. After all, your partner has a lot more experience than you!

defer to partner's tactics if you're in a situation where you have to be the disciplinarian text

Dating Someone with Kids: Pros and Cons

You mature and learn to be more selflessThere are additional expenses, like a babysitter
You get to have DOUBLE the relationshipYour partner may not have as much time for you
You have the perfect excuse not to go do things!You may have to deal with the ex
You’ll have a lot of laughs 😀 You may experience neglect and jealousy

Take the Decision Seriously

Dating someone with a kid in your 20’s is a huge decision that will completely change your life as you know it. Your Friday nights might consist of collecting acorns, watching Paw Patrol and turning in at 8pm. But more likely than not, those sacrifices will come with immeasurable rewards. Maybe your partner’s child will call you ‘mom’ or ‘dad’ someday. Maybe they’ll make you a better person. Maybe they’ll make you rethink your priorities in life.

You never know until you take that step. Dating someone with a child isn’t for everyone, and you shouldn’t string things along if you aren’t in it for the long haul. Otherwise, their kid has to deal with the same feeling of rejection that your partner will go through. Seek advice when you need it, communicate with your partner and surround yourself with a great support system (that loves to babysit for free!).

Do you have what it takes to be a parent? Take this quiz to find out:

Looking for some tips when dating someone with a kid? Watch this video:


3 Responses

  1. Elizabeth says:

    I had no idea you had a blog! Love your honesty. It’s hard for me (most of us probably) to even imagine being on either side of this.

    Keep writing (:
    (This is Mary’s sis)

  2. Alex Froggy says:

    What a vulnerable and honest post on the challenges and rewards (as well as advice) of dating someone who has a child in their 20s! I would like all posts to be directly deposited in my email, if possible please. 🙂 The content’s great. Loved it! Thank you for sharing your heart and mind with the world; it makes the world a better place.

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