The Hottest Thing in 30-Something Dating


“So, do you come here often?” I asked awkwardly.  Oddly, I don’t ever think I used that line in my twenties I thought to myself.  He answered an enthusiastic “Yes! Every week for about 6 months now.”  We were sitting just a couple of seats apart.  He was about my age maybe a little younger, fit, tall, well-dressed.  

“Um, would it be weird if I ask you for your wife’s number?” I followed.

“Not all!” He chimed.

We both whip out our phones, and I text something along the lines of, “Hi Meg, this is Desiree! Chloe and my son Griffin really hit it off in Brazilian Jiu Jitsu, and your husband gave me your number so we could coordinate a playdate.  Hope to meet you soon!”

I never got a text back.  Maybe I heard the number wrong. Maybe not.   

Family dating is rough.  Not only do you need each parent to be cool, but your kids need to be within 6 months of each other and ideally of the same sex.  If you have two or three kids, then all the kids need to be relatively close in age.  

It’s hard to find your perfect group.   

Admittedly, I’ve been lucky.  My oldest son got invited to a birthday party for a child he barely overlapped with in his new daycare room.  We ended up meeting two friends with boys the exact same ages as my boys, and we’ve been hanging out at least quarterly ever since.  But the three years before that birthday were pretty lonely as parents.

Having spent years focusing on my first startup, I didn’t cultivate a lot of new friendships. Not being from Chicago, I didn’t have a built in group of high school friends.  So when we had Griffin in December of 2011, I had no idea where to find new mom friends.  I remember going to the park that spring and looking longingly at a group of moms with older kids, wondering “When will I find my crew?”

I decided, I’d have to build my own. So I literally started just walking up to random Roscoe Village moms with babies about Griffin’s age (that were clearly out for a walk and some fake social engagement in the form of barista banter) and invited them to the park with me.  One time, we literally picked up 6 women en route.  A few of the friendships stuck and we planned a playdate here and there.

But the process was clunky and awkward.  Text exchanges would be miles long as we tried to figure out dates that work, nap schedules, food allergies, comfort level with dogs (and dog hair), and when husbands would or would not be there.  In the end it would often be easier just to meet at the park…until September.  Then we were out of luck.  

This challenge, shared by families all over (but especially in our office of parents), is why we have expanded our vision for Pearachute.  

When we initially launched the platform in early 2016, we started with a “ClassPass for Kids” concept, hoping to make it easy for the parents of babies and toddlers to discover and book great activities in their cities.  We always knew we would grow with our members, introducing new activities and classes as the children aged up.  But what we didn’t anticipate is how much the world would expand when we started to look at the much broader category of family entertainment.

From theme parks to movies to concerts, American families spend about $70B each year on entertainment and hobbies.  This is exclusive of the $30B they spend on their kids’ sports and enrichment programs. And it’s only getting bigger.  

The simple truth is that Millennial parents are busier than previous generations (more dual working parents than ever before), and we want to spend more meaningful time with our children.  We have 27 hours each weekend to play, learn, enrich, and snuggle with our kiddos, and we care more about investing in that time than buying a home.  

We spend 50% more time with our kids than their grandparents did, and we’re looking for meaningful activities to create lasting memories.  

But we’re also inspiring an entirely new chapter of social engagement.  Our Alpha generation kids will be the most photographed and shared generation yet.  They’ll have a social media history often older than they are (thanks to all those ultrasound pics).  

And while nearly all have tablets, few will have phones before the recommended age of 11-13, leaving millions of children with a strong social desire to connect with their friends dependent on their parents for coordinating those activities.  

That’s really where we see massive opportunity for Pearachute.  Our new activity feed is step one in helping parents quickly and easily see what their friends’ children are doing after school and this weekend, so they can effortlessly join them without tons of back and forth text messages or coordinating who will host or pay for the activity.  

Pearachute Activity Feed

With a couple of clicks, parents notify each other that their kids are joining in on the fun, turning a 45 minute taekwondo class into an impromptu playdate you can book the day of.

We know this won’t fix things overnight for lonely new parents.  But we do believe that over the next few years, when people ask parents how they met their new family besties, an enthusiast “Pearachute!” will be a popular refrain…very different than the sheepish “Tinder” we give when talking about our spouses.


5 Reasons Why Bed Rest in 2014 Isn’t So Bad

I’m going on day 7 of bed rest after a scary hospital stay last Sunday night.  The baby and I are both fine, but I’m unable to leave the house for very long, and I’m supposed to “limit stress,” which means working is pretty much out of the question–not so much because GiveForward is stressful but because every email reminds me of how I am unable to meaningfully contribute, which creates stress for my Type A personality.

But, I’m realizing how lucky I am to be living in 2014 with this mandatory rest.  Of course smartphones, Facebook, Instagram, Pulse are all awesome if obvious survival tools, but I also wanted to share some resources that are making my life insanely easier.

Here are my five reasons why bed rest is bearable:

instacart logo




Perhaps the greatest discovery of the year, Instacart has completely changed my stress about having healthy food around for my 2 year old.  Within a couple of hours, I can have anything from my favorite grocery store delivered…including fresh squeezed orange juice, vitamins, and beer for my husband.  I use the service at least twice a week, so I signed up for the $99 for free delivery for a year. Yes, they charge a little bit more per item (maybe 10% or so) but you end up spending less because you’re not picking up things from the shelf that you only want because you’re hungry and well…pregnant.

amazon logo




Two reasons I love Amazon:

  1. Prime: I can get most things I need delivered in 2 days and I don’t have to go to Target.  There were several last minute tasks I was planning on doing before baby no. 2 arrives, and I can do/buy them from my bed!  And it’s even better now that you can watch a zillion shows for free, including every season of every HBO series.
  2. Subscribe & Save:  You save 15% when you bundle several orders together in a month, and if you have Amazon Mom you save an extra 5%.  Because of this and the fact that there are rarely taxes on purchases sent to IL, I end up saving nearly 30% on formula, diapers, deodorant, shower gel, toothpaste…basically all the things that are annoying to run out of.

sanebox logo



This email tool is awesome for so many reasons, but I’m finding SaneBox particularly amazing right now being home.  It basically serves as your executive assistant for email and filters out all of the newsletters and unsolicited emails you receive so that only emails from people you know and care about get into your inbox.  The rest goes into a Sane Later box that you can peruse at your convenience. It’s awesome. The reason it’s so helpful now is that I can just look at emails from my team and I don’t have to deal with any of the clutter of outsiders in my inbox.

sittercity log



After a 5 week medical leave, my husband headed back to work last week.  My bed rest couldn’t have come at a worse time.  I can’t pick up Finn, so I can’t really be alone with him for any extended period of time. I don’t really want to acknowledge how much we’re going to spend on additional help over the next two weeks or after my scheduled c-section which will leave me in the same predicament.  However, the silver lining is that I do actually have help, and it’s easy for me to get additional help because of sites like SitterCity.  All of our nannies and sitters have come from SC, and I’m so grateful it exists…especially now.

homejoy logo



Having grown up in a home where we did our own housecleaning, I actually get some weird pleasure out of cleaning my own bathrooms and floors.  Because of this, we don’t have a regular cleaning person.  But because of awesome startups like Homejoy, I can just schedule one whenever I need it for $20/hour.  It’s pretty awesome.  It’s kind of like UberX for housecleaning 🙂

I would love to hear any other tips for things I can do, apps I can play, sites I can enjoy during my confinement.  Oh, and if you have any great books on getting ready for baby no. 2, I would love those too!


Mother’s Day 2014

Jenna's family is uniting to help her fight brain cancer.

Jenna’s family is uniting to help her fight brain cancer.

This Mother’s Day will be the third time I get to celebrate as “mommy” to an adorable if trying 26 month old.  In the midst of terrible twos it’s tempting to delude myself that the day will be a much deserved 12 hours of all about me time with presents, flowers, delicious brunch, and lots of cuddles from my handsomely clad little boy.


Mila is fighting Stage IV Pancreatic Cancer. Please unite to help raise funds for her mounting medical and living expenses.

In reality, I know the day will be much different.  He’ll have no idea that Mother’s Day is not about Batman and Umizoomi.   There will still be a fight at bath time, a refusal to wear a button-up shirt, and a wait at our favorite restaurant.

The truth is that the beauty of Mother’s Day will happen in the moments in between all of my expectations.  It will be the cheerful “Mommy!” I get as I enter his bedroom when he wakes up.  It will be the handclapping wiggle celebration when we get ready for the park.  And it will be the slobbery goodnight kisses that I get after we read each of his three “night-night” books.

This is really what we mothers live for… the small moments of peace and affection from the people little and grown that we love more than life itself.

Mary was taken just a few days after delivering her twin girls.

Mary was taken just a few days after delivering her twin girls.

But for many moms on GiveForward, these moments are much bigger because there’s a chance this tonight’s “night-night” kiss will be one of the last.  The amazing thing is that none of them live their lives that way.  They all fight, they all thrive, they all give everything they have to be there for their families for as long as they possibly can.

Equicha friends and family are helping her battle breast cancer.

Equicha is facing breast cancer.

With 4 weeks left to go in my pregnancy with baby number 2, I find it increasingly hard to read their stories of triumph and bravery in the face of the unknown without tearing up.  I’m sure you will too.  But my hope is that you’ll be inspired by their journeys to appreciate your children, your health, and especially your own mom that much more.