skip to Main Content
Dating A Man With Kids | CrunchyTales

3 Things To Consider Before Dating A Man With Kids In Midlife

3 min read

Dating when over 50 is already quite daunting, especially if you have ended a long-term marriage and never thought you’d be back out there again looking for love. So, starting a brand new relationship with a man who has kids might be even more complicated. 

Of course, no relationship comes without risks or baggage for that matter but in this case, your partner’s priority will most likely always be his children, her ex may still cause a little stress down the line, emergencies will inevitably come up, schedules will shift, and your plans might have to go by the wayside – and that can be quite difficult to understand if you don’t have kids of your own and you’re ready to embrace the next chapter of your life full of expectations.

Essentially, you’re not just dating him, you’re going to become part of his family structure in one way or another.

Having said that, nothing can stop you from dating the one who can finally make you feel those butterflies in your stomach again or the partner you have great sex with but it wouldn’t harm asking yourself: “how will I handle the whole situation when things start to get a bit more serious?” 

CrunchyTales has got you covered. Here are a few things to consider before dating a man with children.

His kids will always come first

There has to be patience, perseverance, and a positive attitude to find an arrangement that works for all. Your partner may have conflicting feelings and you need to be sure that it’s the type of relationship you can handle. 

There will be a custody schedule that you have to fit into, along with school runs, homework, extra-curricular activities, loud temper tantrums, and more. Your evenings, weekends, and holidays will all be dictated by the kids’ existing schedules and he may not be able to go on adventures you’re looking forward to. 

Ask yourself: “after all those years on a quest for a fulfilling path, now that I’ve finally got free from societal pressures and boundaries, now that I am happy to experience the second half of my life to the max, is that really what I want?”

You may have a hard time finding your role

If you’re really emotionally into him and want to take this forward, an essential factor you need to consider is how much your lives are in sync. 

Sooner or later, you need to ask your partner the kind of role he would want you to play in his children’s lives. Should you be actively involved, or does he want you to meet his kids only during holidays and special occasions?

SEE ALSO:  On Dealing With Empty Nest Syndrome

Whether you like it or not, the kids have a mom who is not you. The way she parents will affect you and the way you co-parent. And you will never be a replacement for the kid’s real mom.

This is what people mean when they talk about the “baggage” of dating a man with kids. You’re not just getting him; you’re getting his kids, his ex, and everything that comes along with that unit. Plus, you’ll hear a lot about her ex. Can you cope with that?

You might not love his kids

The best-kept secret of step-parenting is that just because you fall for your partner, it doesn’t mean you’ll take to their children. The truth is, you’re more likely not to, especially if you are child-free by choice

Janet Reibstein, a psychology professor at Exeter University specialising in family relationships said to The Guardian these feelings are more common than we think but still expect friends to blame you as “categorising the emotions that develop in step-relations is something we haven’t done as a society. We don’t have direct analogies and that’s part of the problem. Instead, we talk about feeling – or not feeling – like a mother, or a bit like an aunt, a sister or a good friend; but it’s none of those. It’s a different and important relationship that needs to be thought through and understood.”

Besides, children don’t always respond well to their dad dating someone new. If things go well, he may end up inviting you to spend time around his children. Depending on their personalities and ages, they may act out, be rude to you, or make things difficult for you and your new boyfriend. If you aren’t ready to potentially put up with some annoying behaviour from his children, it could be a serious problem for your relationship. 

So, is dating a man with kids worthwhile? As with any relationship, there are pros and cons. This special situation comes with its challenges, but it can be a deeply rewarding, insightful and life-affirming experience with the right man. Make sure he is the one before getting involved further.

Like this post? Support Us or Sign up to our newsletter to get more articles like this delivered straight to your inbox!

Back To Top

Learn how to make the most of your midlife journey. Get your Free Pocket Guide on “How to Age Playfully”


Learn how to make the most of your midlife journey. Get your Free Pocket Guide on

Free Pocket Guide | CrunchyTales

"How to Age Playfully"