10 Questions Every Man Needs to Ask Himself Before Dating a Mom


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James, Rachel, Liliana (1), Rosabella (5)

You’re committing to a lot more than being a standard “boyfriend.”

Taking on the responsibility of dating a woman who has children is not for the faint of heart. Below, we’ll discuss some questions every man should ask himself before making this very real commitment.

1. Am I secure enough to take a back seat sometimes?

Every article you’ll ever read about dating a mom will tell you that her kids will always come first. Anyone who has any experience with children knows that they, themselves, are a full time job. Depending on the age(s) of your new love interest’s children, the “full-timeness” will obviously change.

The fact will always remain, though, that her kids will always be her biological, emotional, and moral priority.

This does not mean that there is more love for them and less love for you, but it does mean that these types of love are projected much differently from each other and a man struggling with his own security could feel slighted or cast aside at times.

There is less alone time, less intimate time, less private time, less you time. 

Are you okay with that?

I have always said that I believe two partners in a relationship should make time to prioritize each other in order to nurture and develop the intimate, adult pieces of their relationship, but the presence of children can make these occurrences less frequent.

We must teach ourselves to accept that a lack of time or energy to show us her love does not dilute the love itself.

2. Am I capable of showing what healthy love is supposed to look like?

Daughters will grow up to date men who are like us. Sons will grow up to be men who are like us.

If you take an honest and uncensored look at how you’re living your life and treating those around you, is that a reality you’re comfortable with?

You’re not just committing to properly love one person in this relationship, but however many come in the “package.” Being a strong and positive presence in the life of the boys and/or girls who are part of the equation is something a certain maturity level is required for. I certainly would’ve had no business undertaking this responsibility in the past, which is why I avoided dating women with kids until I was (relatively) sure I could bring something to the table.

3. Am I patient?

Believe me, this one is important.

4. Can I compromise with someone else’s life philosophies?

Entering into an existing family is a completely different dynamic than starting one on your own. Discussions about how to raise children and what to teach them at young ages have already passed, or the children may be old enough to already have their own developed worldview.

Agreeing with all of it is nearly impossible.

Accepting how she is already raising, teaching, and disciplining her kids is something you’ll need to do until you’ve worked to earn enough trust that you can be involved in the process. But if you’re going to start intruding on that space, you will find out quickly just how fiercely a mother will defend (and choose) her children.

5. Can I coexist with the biological father?

Not all bio-dads are still in the picture, but if he is, what are the relationship dynamics like there? Was the separation amicable? What is the custody arrangement?

For me personally, the bio-dad is no longer in the country and plays essentially no role in the girls’ lives, which means full custody at all times of the two girls. If he were still local or if there were shared custody, the circumstances of the relationship would be far different.

It’s up to you whether or not you can civilly and maturely navigate whatever your dynamics will be.

6. Am I willing to bring real value to the table?

Unless she tells you otherwise, a mom who’s looking for a relationship isn’t just looking for a fling.

She is looking for a teammate, a partner, a father figure for the kid(s) in her life. A serious and mature man who can take on an equal role in an adult relationship. This means stepping in at times to help provide for, care for, raise, transport, help, teach, and support the kids.

It means getting off of your ass and helping around the house.

It means doing small things like grabbing that candy you know the son or daughter likes next time you see it at the store.

It means making everyone in the relationship feel valued and included in this new arrangement.

Value is not always monetary. More often than not it shows up in the form of love and service. If you are not capable of bringing this kind of value, then allow her the space to find someone who is.

7. Do I still need constant validation?

If always needing to be reminded of her love is your thing, you’ve opened the wrong door.

Between work, bills, the 24/7 needs of the kids, and all of life’s other realities, a mom is always being needed by someone in some form. This means that the constant adoration and reminding of how handsome she thinks you are, may be in short supply.

She is dating you because you can be a partner to her, not because she’s looking for another child who always needs her attention.

The fact that she is committing herself to you in the first place is the largest indicator of her feelings.

No — this is not an excuse for her to ignore or invalidate your needs — but it is a reminder of point #1.

8. Am I excited about building a life with this person?

We should always ask ourselves this question when we enter into a committed relationship, no matter what the circumstances. But, dating a parent is not something to be taken lightly and therefore really needs to be examined from all angles.

Can you view this person as a friend? A partner? A possible mother to your future kid(s) together?

Does she support you? Laugh with you? Cry with you? As you do all of this for her?

Can you envision the kids when they’re grown and the two of you still together attending life events like graduations or sports games?

When you’re dating a mom you get a glimpse into how she already wants to live her life, how she handles conflict, how patient and compassionate she is. These are all important considerations when deciding whether or not you are really on board for all of this.

9. Can I go ALL IN?

Moms don’t half-ass they way they live, or the way they love. If she’s choosing you as a partner, father figure to her kids, and potential lifelong mate, she is not doing it on a whim and she isn’t going to take it lightly.

This means that you can’t, either.

You must be in a phase of life to fully commit to her and the kid(s).

It may not feel that serious at first. Maybe it’ll be awhile before you even meet the kids. Maybe it’s not “real” yet if you’ve not spent time with them. Maybe you just think you’ll figure it out as you go…but when that reality does come front and center, you’ll understand why your commitment must be total.

10. Will I show up and do my best every day, no matter what?

Nobody is perfect. We all have ups and downs, good days and bad days, stressful days and relaxing ones. Making the conscious decision to become both a partner and a “dad,” though, is a completely new universe to operate in.

This means sometimes getting less sleep, or none at all.

It means sometimes being frustrated or disappointed. Sometimes feeling neglected or overlooked. Sometimes being overtired from work and being pulled in a million directions the moment you get home.

It could mean having your fingernails painted or wearing flower crowns in public. It means dealing with crying babies or children, and maybe even changing them (Yeah, I know…).

It means cooking and cleaning when you don’t want to. Getting up in the middle of the night. Going out for diapers or baby food or batteries for the new toy in the middle of the night.

It also means coming home to love, warmth, and laughter. It means forming a bond with a child or children as a new and important member of their life. It means having the opportunity to step up as a role model and as a guide for how life should be lived.

It means honoring the responsibility of showing children how a man should love his woman and his family.

It means knowing that a woman has chosen you as the man she trusts to help raise her children.

It means committing to accepting all of this — the good and the bad — with class and dignity. It means being the type of man you are confident can raise a generation of compassionate, caring, curious, and healthy members of society.

Stepping into the role of a parent when the children are not biologically yours is an enormous responsibility. Like any other challenge, though, the rewards are waiting for those willing and able to step up to the plate.

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1 Comment

  1. Nosimps on December 24, 2020 at 12:22 pm

    1. Why am I doing this stupid thing?
    2. Why am I doing this stupid thing?
    3. Why am I doing this stupid thing?

    10. Why am I doing this stupid thing?

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