This post is part of my “Ask An Expert” series, which features locals with a niche expertise. What’s yours? Email me at kaylakaplowitz@substack.com with your idea!
For this week's Ask an Expert column, I wanted to do something different. My live chat this morning kicked off a 2-part series called How to Make and Maintain Friends as a Parent.
Part 1 is about how to make them, and part 2 will be how to maintain them.
I'm no expert in this arena, but I'm endlessly curious about friendship in this stage of life. Part of why I started The Plan is to use local events as a low-lift way to connect with parents I like. (e.g., “Hey we’re going to this festival, want to meet us there?”)
My "expert" for this topic is Kaylin Aarts, a Pound Ridge mom of two preschool-aged kids and a leadership coach & organizational development consultant. Kaylin grew up here and moved back during the pandemic. Even though she knew the area, becoming a mom meant building a whole new network of mom friends & couple friendships from scratch.
Last week, she sent me this video featuring What to Cook’s Caro Chambers and smitten kitchen’s Deb Perelman. They played a game live on Substack where each person would describe a hosting scenario (e.g., “What would you cook for a big group in a summer vacation rental?”) and then challenge each other to come up with the perfect spread.
My immediate thought was: Okay, we HAVE to do our own game. But let’s do friend-making scenarios.
Like… what’s the move when you finally click with a mom in the pickup line? When do you decide to go for it and exchange numbers? Who is suggesting the “first date,” and where are you going? How can you tell if they felt a connection too?
If you’ve found yourself stressing about these questions, you’re not alone. We’re all feeling our way through the dark here.
Finding a mom or dad friend is just like dating: sometimes awkward and terrifying, but worth it in the end. After all, every parent deserves a “village.” So I hope our game today inspired you to think differently as you build (or rebuild) yours, brick-by-brick.
Below are just snippets of our answers. Watch the video for the full conversation. 😉
What’s the plan when… you’re at the playground and you keep noticing the same mom with kids the same age and you want to make the first move.
KAYLIN: Remember Brene Brown’s FFT (first f***ing time) philosophy from her 2012 book, Daring Greatly. It’s all about why we all need to normalize and sit through the discomfort of trying something new in order to see growth. Just rip off the Band-aid and go for it.
KAYLA: Couldn’t agree more. But first, I hang back and see how she parents her kids. If she’s treating them like actual humans—and not too helicopter-y, then I’m in. I used to be the one to wait to be approached, but now I have my go-to convo starters to help me just go for it.
I LOVE when another parent notices something great/cute/unique about my kids, so always start with something like that. Guessing their age is always a good opener, too. Show interest. Ask questions. Be yourself.
What’s the plan when… that couple you really clicked with at the last preschool event is going to be at the kid birthday party this weekend.
KAYLIN: My work brain goes to: scenario planning. If you’re near each other, strike up a convo. Or if you’re all chasing after your kids and don’t get to chat, that’s fine too. In your goodbyes, you can always say something like, “I’m bummed we didn’t get to chat because we were chasing these wild monkeys. What’s your cell? Maybe we can do a grown-up hang soon?”
KAYLA: Love the kid birthday party because it’s neutral friend-making territory. A well-run party means your kids are occupied (hopefully), so you get to just chat as adults. Don’t pound beers in the corner by yourself, and don’t be the parent playing with your kid the whole time. Use this time wisely.
Actually, I’m fully convinced that the point of these parties is not to celebrate little Johnny turning 4; it’s to give parents an opportunity to make friends. So lean into that.
What’s the plan when… your kid keeps asking for a playdate with a friend they’ve made at school and you *think* you’d get along with the mom, but aren’t sure yet.
KAYLIN: I’m the one to just go out on a limb here. I’d find an opportunity to mention that my kid has been asking about their kid, and just set up a playdate. I love having people over to my house for a low-key late afternoon hang—you know, coffee for us and snacks for the kids.
My initial pickup line here would be something like “so, what brought you to Pound Ridge?” I mean, we’re raising our kids in the same place, so I know we already have a shared value; the foundation of any good friendship. So that’s where I’d start.
KAYLA: I’ve never been a first-playdate-at-my-house kind of person, but I appreciate it when someone is. I think I’d find the mom’s number in the directory and send a text. I always offer a neutral ground—like a late afternoon snack & hang at Grace Farms—and always have a firm end time so I have an easy out if we’re just not clicking.
What’s the plan when… you see the same mom at afternoon pickup and find yourself really clicking with her. Same humor, same parenting style. She seems great.
KAYLIN: I’d move our relationship to the next step. I’d get her number and ask her out for coffee or a walk. No need for kids. I’m going for one-on-one time.
KAYLA: Same. It’s like, let’s just cut to the chase. We like each other, what are we waiting for?
What’s the plan when… one of those super-connector moms invites every mom in the class to a weekly “come-if-you-can” morning hike or coffee hang.
KAYLIN: Go. In my consulting work with teams, I always recommend setting regular team rhythms because it’s low stakes, and less pressure than big, infrequent, high-stakes meetings. A regular structure helps build momentum and keeps you connected.
KAYLA: Go. As Fran Hauser just recently wrote, say yes to the random stuff, even if you don’t know what the immediate upside is. Great friendships can come from anywhere. And if you’re not showing up and taking a chance, you could be missing out. And yes, I get that we’re all busy, but if you can shift your schedule to make it at least 1x per month, it’ll be worth it.
What’s the plan when… you keep seeing “mom’s night out” events pop up in your social feed and can’t decide if they would be terrible or if you should just suck it up and try it.
KAYLA: Pre-pandemic I remember going to a lot of these things. I joined random local Facebook moms groups, went to mommy & me library groups, brunches, wine nights, book clubs. It was kind of exhausting. Like dating.
If I clicked with someone, I made it a point to follow them on Instagram and/or Facebook. (It’s weird if you wait too long; just do it the night-of). Hate to say it, but in this stage of life, social media is so useful. You just continue the connection there and then move it offline if you still have a good feeling about it.
KAYLIN: So an MNO (hey I learned a new acronymn!) could potentially be terrible. But I say suck it up and try it out. It’s relatively low-risk and helps to push yourself out of your comfort zone. In the work setting, these kinds of in-person opportunities build what we call identity capital; they help shape who you are. And that’s a good thing. See these events as a way to practice your new identity as a parent, as a member of a new community. The more you practice, the more comfortable you become.
What’s the plan when… you meet a new mom friend you really like, and then you realize you make very different parenting choices?
KAYLA: Eh. For me, it’s more about how they treat their kids. I can’t see me ending a potential friendship over something like how much screen-time they allow; that’s just dumb. It’s rare that you’ll 100% agree on every parenting choice a friend makes.
Again, my deal-breaker is how a parent treats their kids. So as long as that’s not an issue, my main concern is whether I connect with you as a person. I guess just figure out your own deal-breakers and go from there.
KAYLIN: This is a tough one. Though something I always try to stand by in my relationships (personally and professionally) is the notion of unconditional positive regard. Everyone is making the right choices for them; even if those choices are different than my own. In my coaching work, one of my core beliefs is that all people are “naturally creative, resourceful, and whole.” This allows me to approach others with curiosity and empathy rather than feeling like they need to be “fixed” or directed.
So, unless they do something that’s a clear deal-breaker, I’d continue exploring a friendship.
And that’s it! Thanks to:
Kaylin Aarts, a leadership coach and organizational development consultant who helps individuals and teams cultivate intention, action, and fulfillment in their work. Through her coaching and consulting, she empowers leaders to step into their potential and build stronger, more purpose-driven organizations. She and her husband live in Pound Ridge with their two kids and Bernedoodle, Bru. You can find her online at @kaylinaarts and kaylinaarts.com.
Make sure you download the app ahead of time so you can join our next live sesh about how to maintain friends on Monday, March 31 at 12PM!
RESOURCES
Local moms / dads groups
Fern Hill Project – Wonderful grass-roots local organization designed to help working women connect.
Bedford Books Book Clubs – They’ll do BYO book events, and regular monthly meetings. Go and you’ll become a Fran-girl like us.
Ridgefield, CT Moms Facebook Group – You’ll see opportunities for connection here all the time.
Ridgefield Father’s Club – Heard good things about this one!
Drop a link in the comments and I’ll add to this list!
Books / newsletters / podcasts / Instagram influencers
This American Life: Why Can’t We Be Friends? – Two dads go on a blind man-date. Just trust me on this one. It is so good.
@KelseWhatElse – This Insta-influencer has been posting SUCH great tips, advice (and actual scripts) you can use to go out there and make some friends anywhere. My must-watch is the video of her 10 Step Plan to Making Friends as an Adult. Love her.
Big Friendship by Aminatou Sow and Ann Friedman – This book is a breath of fresh air.
The Double Shift by Katherine Goldstein – An amazing newsletter about ideas and solutions to care for our families and communities. She also has a paid subscriber section called the How to Find Your People Club which looks so good.
Platonic: How The Science of Attachment Can Help You Make—and Keep—Friends by Dr. Marisa G Franco.
Share this post