Mother-Son Dates

I recently had a mom who is a few years behind me in this parenting journey ask me how to connect with her sons as they grow from little boys into preteens, teens, and into adulthood. Please note that I do not claim to be the authority on this but I do feel I have a good relationship with my sons and would love for my friends to experience the same with theirs. One suggestion I gave her was to “date” each kid on a regular basis. That doesn’t have to mean “often,” but regularly. In a perfect world I’d love to take each kid out once a month but in reality, that never happens. There has never been a year where I’ve managed to have five dates a month, all 12 months. Just hasn’t happened. What I have managed to do is let them know that dates are a priority and that we’ll rotate through the bunch and then start over. Some years all I’ve been able to manage is one date a month, which means each kid only got two dates… but at least they knew it was coming. They knew I was looking forward to it.


  • The kid chooses the date.
  • Must be cheap (I set the parameters – lunch or just coffee/ice cream; movie; a paid activity or something totally free…)
  • Just us. No siblings, no other parent.

Here is something for the mom considering starting dates with her kids, specifically her sons, to remember:

These dates are rarely magical or even memorable individually. But they are memorable cumulatively.

They’ll remember that their mom or dad took them on regular dates (even if it wasn’t often). Just last week I took Bailey to a diner on Coney Island and he told me that one of his friends couldn’t imagine going on a date with their parent. Just not part of their family culture… Bailey seemed to think that was the unusual family dynamic. I wonder… My kids will probably not be able to tell you the specifics of dates they have had with me but they’ll remember that we’ve been on many together.

I told that mama not to be too worried if she took her son on a date and when she got home, wondered, “Did he even enjoy it?!?” He did. He just may not show it. SHE may be looking for deep, intimate conversation and connection. He’s not. He’s just living his life and doing something mom said they were going to do. But as an adult he’ll look back on his childhood and remember that mom regularly took him for dates, just him, and it will mean something to him.

Another thing to remember, many boys do better “shoulder-to-shoulder” rather than “knee-to-knee.” What that means is that many boys will talk more or are more likely to open up if they’re doing something side-by-side than sitting face-to-face. Likewise girls tend to prefer the “knee-to-knee” or face-to-face, just chatting and connecting. So, moms, gauge your kid. He very well may be the kind of person who loves just sitting and talking, and that’s perfectly fine. But for most boys you’ll have better success if you are both doing something, even something as simple as walking.

For those of you who are wondering about the mother-daughter connection, or why I wrote this from a mother-son perspective, I have a few thoughts.

  • I was a boy-mom for 15 years before having a daughter so the vast majority of my experience is related to the mother-son dynamic.
  • Father-son relationships are not my specialty… you’d have to check in with Matt. (But I will add that the vast majority of Matt’s interactions with our kids are fun, hanging out, going to concerts, while the vast majority of MY interactions with our kids revolves around teaching, correcting, instructing, redirecting… and thus, dates with my sons where we are just BEING together are critical for our relationship. I may or may not admit to being a little jealous of the father-son dynamic some days.)
  • Mother-daughter and father-daughter dates are just as important, I just don’t have as much to say about those right now as our daughter is only five years old and we get some pretty good fun-time just hanging around the house. Because she’s the only girl and because she’s six years younger than the next sibling, there are many times we are together, just BEING, while the rest of the people are out of the house. And she’s at the age where I can call errands “a date” and get away with it. As she ages I will prioritize her in the rotation as much as I do the boys but so far, I’ve been able to do plenty of “girl-dates” with her.

Happy Dating!!

About Jennifer

"Yes, they're all mine." The answer to the question I hear most often.
This entry was posted in brothers/boys, family, Motherhood Musing. Bookmark the permalink.

3 Responses to Mother-Son Dates

  1. Janet says:

    I have loved the idea of this for a while now and want to intentionally make this happen! We are entering a new season of life and some really big transitions in our family. Any suggestions on the activities so that we are “doing” (shoulder to shoulder) something rather than at an ice cream shop and knee-to-knee? My fourteen year olds aren’t excited about it. They aren’t excited about much of anything these days. I’m thinking I will need to have a few activity idea suggestions to help them brainstorm at the beginning. I appreciate any hints on some things you have enjoyed over the years.
    Thank you!!

    • Jennifer says:

      I should have listed a few ideas in the post!

      Our go-to was always coffee or lunch. We eat at home most of the time so eating out is always a top-option for all of my kids.

      One of my favorite memories is taking each of my kids out to learn how to take public transportation in Germany. We had no idea we’d be moving to New York City and would absolutely need that skill! I took them one-at-a-time and they picked the destination.

      Bowling is always a favorite. Pick a day that your local bowling alley has dollar-pin days. 🙂

      Walking – neighborhoods or local parks.

      I’m drawing a blank at the moment but I’ll try to come back and add more as I free-up more brain space.

  2. Sybil Kee says:

    Love this Jen. Not only are these dates important as your children are growing, but I have thoroughly the times I have spent with my adult men. The love is there, but the relationship is even more special.

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