Brother and kids in the fields

Dating a Man with Kids: Pros, Cons and Things to Know

Last Updated on June 24, 2022

Dating in your 30s is very different from your 20s – know some fish in the dating pool are fathers (and not just creeps wanting to be called ‘daddy’).

At first, this might not seem like a big deal in exchange for meeting the love of your life, but dating a parent can be a challenge. Men might not have full custody of their children as frequently as single mothers, but they’re priorities are (and should be) focused around their children’s needs.

This will look different for each father or each single parent, but it can look like this:

  • At the last minute he receives a call from his ex-wife that he needs to take the kids for the weekend – and now your weekend ‘extra curricular activities’ with him are ruined
  • At home his kids are fighting for dad’s attention while you’re in the middle of an argument or important conversation
  • You want to schedule a date night but he says he needs to spend time with his kids while they’re at his place.
  • You’re finally having alone time with him and his attention seems to be elsewhere

But don’t despair yet: dating a man with kids does not have to be difficult or inconvenient if you just change your perspective and patience threshold.

  • So he has to take the kids for the weekend and you can’t have the crazy, hot monkey sex you wanted – but now you get to see him play and interact with children. You can watch him transform into a softer man with healthy relationships with his family.
  • You might need to talk to him about something right now but his kids might only get to see him rarely because of a tricky divorce settlement. Taking a time out from each other, and playing or chatting with his kids can be a great way to de-escalate a fight and get the perspective you both need.
  • What’s more, you probably remember what it’s like being a kid and wanting to excitedly show your dad something and have him totally invested in your world. Don’t be jealous or possessive over a dad because you’ll end up taking away precious childhood moments from his kids lives.
  • He needs a little space and time with his kids – again, you don’t want to take away moments from a childhood. This time apart may be upsetting, but you could use it for selfcare, running errands or planning a special date with him later on. Dating (any man) takes up a lot of our time, and we can forget to treat ourselves right when we’re caring for another. Use the unexpected delays and rainchecks to invest more care in yourself, because you deserve it.
  • There are so many books, podcasts and so-called experts on parenting telling mothers and fathers how to raise their little ones, but it’s still so overwhelming. Now add in all the complexities of trying to raise kids with divorced parents while still trying to give them a ‘normal’ childhood… it can leave a man overthinking every conversation and moment with his children. But, it can be extremely frustrating to talk to a man and know his mind is elsewhere, but be patient and ask him what’s on his mind – a burden shared is a burden halved.

Good communication and patience are what build strong foundations in a relationship. If you’re feeling under-appreciated or annoyed – tell him. He already has a couple people in his life who are demanding and don’t properly communicate their needs and feelings (and those people are under 18 years old)

He might be a father, but he’s still a man – and men are notorious for not sharing their feelings and thoughts. If you ask him and create a space where things can be spoken about freely and healthily, your relationship will reap the benefits. Once lines of communication are open, all the little inconveniences, disruptions and annoyances can be discussed and worked through.

When dating a man with kids, your communication skills, patience and emotional sensitivity will need to be important soft skills to remember.

Red Flags and Things To Remember:

Red flag

When dating a man with kids, we need to still remember our standards, boundaries and needs. He may have children but he is still a man and can make mistakes and act poorly – don’t let his kids create a blind spot for you.

Below are some warning signs and red flags to look for:

He doesn’t have any boundaries for his children – Children need stability and structure, ‘rules’ might seem unfair as a child but as an adult we understand their importance. If he doesn’t set any boundaries or rules for his children (eg. set bedtime, etiquette at dinner, screen time limits etc.) he won’t set or understand boundaries in your relationship. He might think it’s alright to show up at your house at 2AM, he could think it’s okay to speak to you badly or even show disrespect for the boundaries you outline to him.

He asks you to babysit his kids – As a parent, caring for and looking after his own children is never ‘babysitting’. If he asks you to babysit while he goes to visit his friends, that’s a red flag as it shows he only thinks of his children as people to caretake and the caretaking can be someone else’s responsibility and not his own.

When his kids are over, the house becomes a disaster – A little mess and chaos is normal when children are around. Put learning to clean up and re-set the house is a vital lesson to children. If he lets the kitchen, living room and bathrooms become giant messes for the maid, himself or even you to clean after they leave… major red flag. It shows a lack of responsibility, poor communication as well as an inability to demonstrate good behaviors to his children – he should be able to say “alright! That was an awesome cupcake baking session everyone but now we have to clean up, Becky you’re on dishes and Josh is going to dry them while I pack everything away”.

He lets his children disrespect you – We’ve all watched the Disney movies with an evil step-mother, but in reality, having a step-mother is fairly uneventful and perfectly normal. If he allows his children to antagonize or villainize you that is the real evil act. You should be another adult figure to them, and actually someone they can feel close enough to that giving advice and affection aren’t misplaced or awkward. Of course, there are adjustment periods where the children might feel you overstepping or that you’re ‘trying to be their mom’ – but their dad should always step in and make sure that a healthy relationship progresses.

Pro – He’s Family Orientated

Father and daughter in the kitchen

Very often when dating we come across men who aren’t ready to settle down or we get into situations with men who say they aren’t ready for a committed relationship. A man with kids has already settled and committed himself. He understands how important family can be and regularly makes an effort to provide and plan for a future.

But this doesn’t necessarily mean he’s ready to dive head-first into a new relationship – this man might have some emotional baggage and anxiety when it comes to relationships, marriage and his new unknown future.

Again, patience is key.

He has commitments and priorities in his child, his ex partner and his full time job – but if everything goes well he may soon realize you are the right person and then his orientation will shift to including you into his family. And then you’ll appreciate and benefit from his dedication and sense of priorities.

Pro – He’s More Mature

Dating
Two unrecognizable businessmen having business talk over coffee sitting at table in cafe. Laptop, coffee cups and smartphone on table. Focus on hands and cup of espresso

Online dating can be hell, and it’s because so many apps are populated with immature, cheesy and emotionally unavailable men.

But a man who has children and has had a past committed relationship is more likely to act maturely and responsibly. He’s had experiences (and learnt lessons) from his previous relationships and it will benefit your own relationship with him.

Many of his ‘firsts’ have already happened – he’s been married, had a house, bought a car, etc. While it can be sad to have missed out on so many monumental moments, so many of his ‘learning curves’ have already happened as well. You may not have lived in his first home but now he knows how to clean properly, pay rent on time and haggle with a realtor to get a better lease agreement.

Because he’s a father, he has less time and energy to engage with pettiness – so if you’re the type who loves a good fight, a single father is perhaps not the man for you.

Pro – He Will Give You Stability

A man with kids has a lot of commitments to balance. He has to manage his time carefully and to fit in line with his children’s routine.

This means date nights will consistently be on the one or two free days of his week. If you love a spontaneous day trip or adventure, this man might not be able to always surprise you between his work, children and errand runs. But if you have been wanting to slow down and have more ‘nights in’, this man can give you that stability and comfort.

If you’ve been exhausted and drained by the ‘hook-up’ culture that celebrates playing emotional games between partners – the good news is that this man is too tired from a 5 day work week to play any games (that aren’t with his kids).

Con – He May Be Rusty with Romance

Since becoming a single parent, he may have only just started dating again. Which means he might not say the right thing, or know the trendiest restaurants.

There may also be some intimacy blockers – he might not have had sex for a long time and so things may be a little rusty and awkward. But if you’re patient and give him lots of love and affection, it might make it easier for him to talk about his feelings and reciprocate yours.

Depending on how old his kids are, his children might still need and enjoy co-sleeping with their dad. This might make intimacy and connection even more difficult for him when he’s still so connected to his children. Talking about how you feel and how he’s feeling is a great way to build non-sexual intimacy, if sex is off the table for now. Building the tension through flirting, sexting and other means can also boost his confidence before sex ever takes place.

Con – Being Introduced As Dad’s ‘New Friend’

Baby and Parents
Asian baby (12 months) boy takes its first steps with his family in forest. Thailand.

When meeting his children for the first time, it’s only natural that he might down-play your relationship. Kids are suspicious creatures and they might have their guards up towards ‘dad’s new girlfriend’ but time mends everything.

The first day might not go perfectly, but consistency is the secret key to relationships with children. At this point in their lives, they mostly remember things through repetition. If you are consistently friendly, helpful and kind, the kids will remember and relate to you as such. But if you’re hot and cold, that can be confusing to them.

A child’s love language is often quality time – so play, chat and engage with them as much as possible. After the initial 30 minutes together, things won’t be so awkward and they might get to see the reason dad brought ‘a new friend’ around. It will also help if you can have your own joke or special game with them, soon you won’t just be ‘dad’s girlfriend’ to them and they won’t be just your ‘boyfriend’s kids’ to you either.

Con – His Children Might Not Like You

Not everyone gets along and that’s natural, but this relationship has a hurdle in its lane from the beginning.

They might feel like you’re ‘replacing’ their mother, of course this is not true but we can’t blame children for their feelings. The responsibility of conversation and civility is on you (because you’re the adult), so get to talking and playing as soon as possible.

What can make things better, faster is if you avoid ever drawing lines between you, their dad, their mom and them. Everyone should be included and accepted in this family. Make sure that all jokes, games, movies and activities are inclusive and enjoyable for everyone.

Here are some simple guidelines to follow:

  • Don’t leave any children out of the conversation – If there are age gaps, you might develop a relationship with the younger child while the elder ones are still suspicious of you. You could feel tempted to only talk to the happy little one but the elders might see this as a slight. We suggest plop the little one on your lap and still talk to the others so that everyone is involved.
  • Don’t talk badly about their mom – Who knows, she could be a terrible person, but she is still their mother and you cannot antagonize her. If she ever comes up in conversation, allow the children or your boyfriend to take the lead – but don’t completely disengage either.
  • Always let their dad take the lead in parenting – You are an adult figure to them so you can dictate bedtime and proper behavior but only if it’s been authorized by their dad or mom. You might think things would work better one way and it can be tempting to enforce improved rules, but these aren’t your children and it might only further alienate you from them (when you become an authoritarian figure).

Con – His Finances May Be a Mess

Mother and baby

Money is always a tricky situation for new relationships but for a man with kids, it’s a daily reality check. Divorces and alimony are expensive, child support is expensive and giving his kids everything he wants them to have is (you guessed it) expensive!

Despite having a full time job, this dream guy might be broke. Good communication will be the way to navigate you both to the shared life and experiences you want. But combining assets and accounts can be tricky and not for everyone.

For new relationships, we’d advise not acting hastily. If you want to take a big Hawaii trip together but he can’t afford it, give him time to save for it or downsize the plans a bit. Don’t pay for the whole trip for him, because this might set a precedent that you can bail him out financially when he needs it – and you are not his personal bank or line of credit.

For more settled relationships, we advise healthy money sharing and behaviors. He has been divorced or separated before and has an understanding of what might have worked or not worked for him in the past, will that work for you? Ultimately, you want to make sure neither of you will feel obligated to pay for everything, all the time. If you share a life, you share costs but how things are evenly divided will be different for each couple.

Cons – You May Not Be His Priority

His children will and should always come first.

It sounds harsh but as a father he has responsibilities and commitments that came before your relationship. Not to mention many single dad have limited time with their children per their agreed visitation schedules from their divorce.

He might need to cancel a date last minute because he forgot a parent-teacher meeting, but that meeting is vital in understanding his child’s development. You cannot expect to come before you boyfriend’s kids – if you do, it will strain the relationship and likely end it.

Instead of seeing this as a ‘con’ think of it as an investment and preview for how he might prioritize any children you have together. Witness, watch, learn and understand how he acts as a father, mentor, advisor and educator to his kids.

Is he kind and gentle? Does he let his kids walk over him or does he maintain firm and fair boundaries? Is he a good dad?

Every moment and memory with his children could be a preview for your future together.

Moreover: you could show interest and passion for his children by asking about his parenting approaches. What does he think of liberal and progressive gender norms? What does he think makes a good parent? Does he want more children? What does he expect his children to achieve or participate in? What does he wish his parents did differently when he was a kid?

Father baby sitting and talking on phone
Busy Latin American father multi-tasking at home carrying the baby while talking on the phone – lifestyle concepts

Cons – The Other Woman Factor

You are not the mother of his kids, there’s another woman in his life and to her you are the ‘other woman’.

Dating a man with kids means there will be a third woman in the relationship and it can be challenging for everyone to keep the peace. It can help to keep these things in mind:

  • Their relationship is in the past and yours is in the present – there shouldn’t be any romance or flirting between them. If you notice suspicious behavior or interactions bring them up calmly with him at another time when you’re alone.
  • They are the children’s parents and you have to respect their parenting decisions – You will be spending a lot of time around his children but you have to respect her parenting style. Don’t overstep their boundaries and create conflict, if you want to introduce something to his kids always ask first.
  • Jealousy is natural but keep it in check – Have a friend or therapist (not him) that you can confide your feelings to. You might see him and her acting friendly and think it’s suspicious but it might be nothing. You don’t want to bring these feelings to him as it will create a wall between the three of you, and you will be the one bricked off and left alone. However, it’s important you don’t bottle these feelings as they can become toxic and unhealthy if they’re always contained, which is why a trusted friend can be great.

Just remember, they divorced for a reason, things didn’t work out and they’ve built separate lives now.

His children’s mother is not supposed to be your enemy, she might even be feeling just as awkward and weird about the situation. Be friendly and open about the situation and you might just gain a valuable friend and ally.

Family Day out

Final Thoughts

There may be many challenges and struggles when dating a man with kids, as our list shows more cons than pros – but in any serious relationship there are struggles. But dating a man with kids can be the perfect relationship and situation for many women (especially women looking for older and more settled men).

We really believe that with emotional sensitivity, patience and good communication the many emotions of dating a man with kids can be processed and overcome. It’s all about getting onto the same page with your partner: they have priorities and part of your romantic life together will involve navigating those. At the same time, you have needs and desires that must be met and even a man with kids should meet those standards.

John Santana

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