Jack Giarraputo Productions

The Good, The Bad And The Ugly Of Dating A Man With Kids

I have a friend -- let’s call her Jane -- who only dates older men. The span of time between their respective ages never seems to really matter, as long as they are older.

Usually, her limit tips at the 10-year mark, but sometimes, she will make a concession for 15 or 20. If his hair is aptly salt and peppered, she will even dip down to a solid five years older.

On the one hand, when we were in our early 20s, this was a little skivvy. I could never understand what a recent college grad would have in common with someone I considered to be a parental figure.

On the other hand, as we have grown a little wiser, the idea of having a seasoned love interest has become more appealing. Older men tend to be more skilled in many aspects that appeal to women.

The conversations are almost combustible with their content of interesting opinions on politics, literature and music. They are, more often than not, financially stable, responsible and more imaginative.

Who cares if their nights out start and end before we even begin our happy hour? Those afternoon naps they are tied to can be filled with lots of fun.

The older man is an interesting option for a girl looking to broaden her dating experience.

But, here’s the thing: When it comes to dealing with the proverbial “older man,” there is a bevy of baggage that comes along with it. Most notably, that baggage involves kids.

As one who is still not sure I ever want to delve into the abyss of parenthood, I am always a little leery about this particular type of baggage.

Would we happily play out our endeavors with fun trips to the park, exciting vacations to kid-friendly corners of the world and enjoy giggle-filled pizza nights?

Or, would I be dealing with an avalanche of unchartered territory and drama?

Children, don’t get me wrong, are joyous beings I'm sure, but even with my large experience working with them professionally, would I be content to thread them into the fabric of my day-to-day life?

The question looms: Is it ever a good idea to date a man with kids?

I did my research and have come up with the good, the bad and the ugly of what it is really like to date a man with kids.

All of us fall in love differently, so I am bringing this to you in the spirit of Gary Chapman’s work on the “Five Love Languages.”

In his work, he talks about the five various ways each of us gives and receives love: Words of Affirmation (compliments), Acts of Service (doing for you), Quality Time, Receiving Gifts and Physical Touch.

It is in this way I want to break down what it would be like to patter down the path of romance with an older gentleman.

Helping to comprise this list of experience are women I surveyed who have dated men with little ones.

Their experiences, reflected in this list, have graced them with a plethora of lessons, some of which are too naughty to share, but all of which should help you to decide if it's ever a good idea to date a man with kids.

1. Quality Time

If you are a lady who loves lots of time with your man, the man with kids may NOT be the best option for you.

One thing you need to understand is this: His kids come first. If that fact doesn’t detour you, be ready to receive some of the benefits that will inevitably come when he does get around to calling you.

The Good: He will cherish his time with you.

The man with kids doesn’t get a lot of one-on-one adult time, especially if he is the primary parent. When he does get it, however, he will appreciate it. Make it fun and exciting for him, and he will keep coming back for more.

The Bad: His time will be limited.

He simply won’t have a lot of time to court you. Do not expect the time you two spend together to be consistent.

If an everyday encounter is what you seek, then keep it moving, sister. This guy will be in constant contact when his kids are not around, but once they arrive for their dad time, he will go ghost.


Newsflash: If he has kids, he has a baby mama. Even if they are no longer an item, the fact that a new woman is taking the time and attention of her former lover will affect the "baby mama" on some level.

If she is still remotely enamored with him, this will not sit well with her — especially if he introduces you to their kids.

Be aware that if you become a solid part of his life, you might have to deal with the natural jealousy of the one who “came before you.”

2. Words of Affirmation (Compliments)

The Good: You will always be younger, hotter and sexier than the mother of his child, and he will take every opportunity he has to tell you how amazing you are.

Men always date up, they just do. Because he came out of a situation where he got the prize (his kids) without the package (their original family unit), he will look at you as if you are heaven sent.

You are his angel because the two of you have not endured the obstacles that broke them apart. He will take every opportunity to bask in the glow of your budding relationship, and may often make a comparison in your favor.

Enjoy this. Just make sure you are never the one doing the comparing.

The Bad: He may be out of practice.

If he is divorced and just now starting to date, he may not remember how important words of affirmation are.


Competition: You will always be hers (even if she has moved on). It takes time to create a harmonious co-parenting relationship.

If these two have not completely crossed this bridge, please be advised you will be walking into a contest even if you are not a willing participant.

3. Acts of Service (What You Guys Do Together)

The Good: He will love doing anything with you that is a distraction from the mundane duties of his life.

This is especially fun if you guys get serious, or if the dating turns into a marriage. Coming into a family dynamic from the outside gives you the opportunity to be a friend to his kids.

If you become his wife and a step mother, you will always be the “fun” parent. The daily duties of disciplining his kids will fall primarily on the mother and your partner, which means you are left free to plan all of the fun stuff.

The Bad: If you do end up being with this guy on a permanent level, all of the things you do together that are firsts for you might be old hat to him.

For example, the magic of the first-time pregnancy will be lost on him. He has been there and done that, so although he may be excited, don’t expect those initial tears of wonderment.

His mind is already churning with figures from diaper costs, school tuition and hospital bills. This is not his first rodeo, and often, the wanderlust is already gone.


If she is petty, she may take any opportunity to rain on your parade. If she is well-adjusted to the change of not having him in her life, you will have to endure the niceties of including her.

4. Receiving Gifts

The Good: He will appreciate your energy toward the little things where his interests have already began to dull.

So, the fact that you want to celebrate the anniversary of the first time you guys met, or start little traditions centered on your own inside jokes, will be refreshing to him.

He will love that you leave little love notes in his pocket and feel satiated every time you squeal with joy at the little presents he gives to you.

The Bad: You will always be a second-class citizen when it comes to gifts.

The guy with kids will always put his kids first. He has lots of other purchases to be “responsible” for, so sorry, that new Coach purse you have been salivating over will take a back seat to the mini league gear he has to buy his son.


She knows that, to him, the kids come first (as they should), and may use this fact to overpower your presence in his life.

Remember, they are not his kids with you, so he will not place you on a mutually-bonded pedestal like he might with her.

The journey of parenthood is not one you will be on with him as an equal partner. His children with her will give him that twinkle in his eye, and if she is spiteful, she might use this fact to your disadvantage.

5. Physical Touch

The Good: This is where you win! A guy with kids, due to practical purposes, is well-versed in the anatomy of a woman!

Not only that, but because he has had to soothe little ones when they are sick and gives hugs and kisses on a daily basis, this guy understands the power of touch.

The Bad: Nada, nothing, zilch! Enjoy it!


He may be reluctant to share all he has learned about how to caress, kiss and dote on a woman he in front of his kids. Just because he has introduced you and included you in their lives doesn't mean he will be comfortable showering you with affection when his kids are around.

The guy with kids doesn’t want there to be an issue in this department. He may not want them to go back and report it to their mother. Not that it should matter, but if she is petty, she will use the information to punish him.

So, there you have it! Some say the good outweighs the bad, but it will be up to you to form your own opinion. Good luck!