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7 Critical Things To Consider When Dating Again As A Single Dad

Things To Consider When Dating Again As A Single Dad

Modern dating is tough but there are additional things to consider when dating again as a single dad that can seriously affect you and your children.

While many of these things should be considered by all single men in the dating world, there are specific things that apply to dads.

In this video, we’ll look at:
  • Dating after divorce or death vs oops
  • How custody affects relationships
  • Having younger vs older children
  • Red flags dads must watch for
  • What NOT to tell your children
  • And what to do if your kids are sabotaging your dating

Things To Consider When Dating Again As A Single Dad

Many of my videos on building confidence in dating and relationship skills apply to single dads as much as men without children.

But there are some specific considerations for single dads (no matter what your access and involvement are with your children).

If you are actively involved with or have custody of your dependent children, your choices also influence their lives.

Being a parent is a huge responsibility and doesn’t stop when you become single or when your children grow up.

Click the image to play the video!

Let’s take a look…


Dating After Divorce vs Death

Both situations are awful and heartbreaking.

Either the person you once loved chose to leave you or it got so bad you felt you had no choice but to leave her or …neither of you wanted to part but now she’s gone forever.

My heart goes out to you.

This brings us to…

1. Don’t Date Until You’re Ready.

This may seem obvious but it’s not.

For men who’ve been in long-term relationships and now find themselves single, that’s a big change, and will often feel uncomfortable and lonely.

Discomfort being alone and loneliness are not the best reasons to date, especially if you’re not truly ready!

You may meet someone you’re attracted to and have a great connection and chemistry with, but she ends up using you and discarding you later.

If this happens over and over when you’re a single dad of young children, they can develop an expectation of uncertainty in life and later an underlying fear of intimate adult relationships.

But choosing poorly also affects you negatively, whether your children are younger or older.

When you’re desperate you make poor short-term decisions that can have long-lasting effects.

You’re probably not ready to date or be in a new relationship if you can’t…

2. Stop Talking About Your Ex

Again, this one applies to anyone, but it’s one of the things to consider when dating again as a single dad because…

…even though modern women can be selfish, any woman dating a single dad still has the nurturing gene tucked in there somewhere!

This means when you talk obsessively about your ex, she’ll unconsciously feel you’ll be constantly comparing her to your ex especially when it comes to parenting.

And it doesn’t matter if your references to your ex are positive or negative!

She knows your ex is still taking up too much real estate in your mind and you’ve got some healing to do.

What if I wasn’t in a relationship with my child’s mother and it was an Oops? Or I’m not involved in my child’s life, by choice or not?

Great question!

Let’s look at how…

3. Custody Affects Romantic Relationships

For those who have dependent children, custody is one of the critical things to consider when dating again as a single dad.

We’ll look at single dads of grown children after this.

The amount of time you spend with your children and whether or not you have legal access to them will affect your prospects with women.

You’re going to attract a different kind of woman if you never see your children (depending on the reason) than if you’ve got full custody.

Just like you should be evaluating a woman’s character, she’s definitely evaluating yours.

And, your situation with your children sets up an expectation for how she assumes you’ll be with her.


You meet a woman you’re attracted to, get her number, flirt a bit, set up a date—woohoo!

But then on the date, she asks you about children.

“How do you feel about them? Do you have any?” Etc.

You can’t lie. She’ll find out and then she won’t trust you.

So you’re honest with her… maybe with a little sugar coating. 😉

If your child was an oops and either you choose not to be involved or can’t be because your ex is a nasty skank…

… her first reaction might be, “Oh, good, no baggage.”

But if she’s got good values, her mental evaluation might be, “Hmm, he makes big mistakes and doesn’t take responsibility” either for choosing to be a part of the child’s life or for choosing his mother poorly.

If you had a relationship but broke up, she’s evaluating.

If your partner went to be with the Lord, she’s evaluating.

Women’s primary need is to feel safe, physically and emotionally.

So she evaluates the kind of choices you make that influence the character you have as a man and how your choices may affect her.

What if you are involved in my children’s lives?

Younger vs Older Children

Ok, so your kids mean the world to you and you have full or partial custody.

They are a priority, they are part of a package deal.

4. You Are A Package Deal, Sir.

Even if they’re grown and gone! More on this in a minute.

Younger, Dependent Children

When they’re younger, they affect your schedule and availability.

If you’re looking for a partner, you must find someone who is ok with that.

And you have to decide what level of co-parenting you’re ok with.

You also have to know where the boundaries of priority are.

Of course, your children’s immediate health and safety should always be your top priority, but beyond that where do your loyalties lie?


Little Jimmy has his first recital and he’s the most important tree on stage or he’s in soccer and it’s the first game, or maybe a mid-season game.

Is that more important than being at her big award acceptance banquet?

It might be to you, but is it to her?

Older, Independent Children

Do you think if you have older children, you’re off the hook?

Not totally!

Even though older or adult children don’t usually live with you—though nowadays they often do—they come with other considerations.

Grandchildren! Babysitting! Family drama!

You still need to figure out where your older children fit into your potential relationship and where your priorities are.

5. Family Values Are More Important Than You Think

Don’t assume she has the same family values you do!

This brings us to…

Red Flags

As I’ve talked about in many other videos, in order to have a chance of a happy, long-term relationship you need to have compatible beliefs, values, and goals.

This is no different when you’re a single dad.

At the same time, not every little thing is a red flag. Some are pink flags and can be worked through or simply accepted.

Dr. John Gottman, a prominent psychologist, and relationship researcher (who predicts with a >90% accuracy a couple’s relationship success by observing them for 5 minutes) discovered that 69% of disagreements never get resolved.

But most people choose their partner based on attraction, chemistry, and connection not compatible beliefs, values, and goals. More on this in another video.

No wonder the divorce rate is so high!

If she…

  • Says she’s allergic to kids
  • Never wants to meet yours
  • Asks about your Will…

…those are real red flags!

You obviously don’t want to bring her home to your children!

But before you meet anyone you’d introduce them to, you should have a conversation.

6. Don’t Keep Your Kids In The Dark

What and When to Tell Your Kids

One of the critical things to consider when dating again as a single dad, especially with younger children, is when and what to tell them.

When to tell them you’re dating? The sooner the better.

You don’t want to spring some new person on them the day after this kind of conversation.

It’s better to plant the seed early and let the idea of dad dating germinate.

They will think about the idea and, depending on their age, they may have questions come up.

The more questions you can answer for your children the safer they’ll feel so when you do meet someone it won’t be as scary for them.

Say something like, “You’ll always will be most important in my life. And as much as I love to spend time with you, and friends and family, just like you do, I also want to have friends of the opposite gender who I can do things alone with.”

This brings us to…

7. Expect Resistance!

Children have loyalties to their mothers and feel guilty accepting another woman in a similar role.

That’s normal.

Your job is to reassure them no one is replacing their mother and that your love for them is steadfast.

Tips for Talking to Your Kids


  • Tell them too much too soon (name, appearance, if she’s got kids is enough).
  • Make them meet every lady you date (or any until you’re serious).
  • Ditch your kids for your date (they’ll feel unimportant and resent her).
  • Dis your ex to your kids (even if she is awful, kids have loyalties).
  • Make the first meeting a big thing (short and sweet).
  • Have her stay the night too soon (wait til you’re serious and they’ve met many times).


  • Understand your child’s resistance is normal.
  • Be patient and respectful with them.
  • Choose well!
  • Know children adjust when you make them feel safe.
  • Give yourself permission to find love again, you deserve it!

If already dating and have tried to talk to them but aren’t getting anywhere or they’re actively trying to sabotage your dating life, I invite you to talk to a family therapist.

If you want my recommendation for great online therapy, click here.

Stop suffering and start making your way toward love again. You got this!

God bless!

Also, watch…


things to consider when dating again as a single dad

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