The Lollypop Project

I encourage my kids to talk to strangers. 

Before you notify the authorities, hear me out. When my husband and I decided to stay in Chicago once we had kids, that meant we were going to have just one car (which he would drive to work during the week), leaving me and the child (and later, children) to depend on strollers, walking, and public transportation to get around. Most of the time it’s actually no big deal. In fact, we kind of love it. My boys know how to find seats, stay seated, and typically they behave.

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Except when they don’t. That’s where the lollypops come in. I started using them as a distraction on our infrequent car trips with the whole family where inevitably my older boy would get carsick. So perhaps it’s a placebo, but if you’ve ever had to clean puke out of a car seat three days in a row then you would do anything to avoid doing it again. Ever. 

These boys like their lollypops. But they are willing to share. 

The lollypops worked like magic. And so when we started taking buses and trains around, the boys were easily bribed for their patience with the promise of a lollypop once we boarded. I stocked up on huge bags of Dum-Dum pops, and kept a stash in our diaper bag for any transit opportunity. 

One day, Davey and I were coming back from errands downtown and ended up on a crowded Red Line train with our stroller. Usually I try to be a Good Citizen of the CTA and fold it up, but I was there with the big model that doesn’t really fold, and a very tired boy who was nearly asleep. I gambled that there would be room on the train. Not a great choice. 

People rolled their eyes and moved aside begrudgingly as I repeatedly apologized and parallel parked the stroller. I hung on to the overhead strap with one hand and the stroller with the other for balance as the train lurched forward. It was rush hour, and people looked us over and looked away, tired and bored, most with white earbuds coming out of their heads. 

In front of us, two big men sat with knees splayed wide. They wore baggy jeans, and their heads nodded under flat-rimmed black baseball caps. Large, muscular arms folded across their broad chests. One seemed to be sleeping, the other gave us a slight nod of acknowledgement behind dark sunglasses as I apologized for bumping his giant high top sneaker with a front tired as I maneuvered my awkward chariot. 

My very-social boy was now up and alert, roused by the sounds of the announcements (“GRAND IS NEXT!”), the clanging doors and the general noise of an afternoon on the CTA. 

“Mommy,” he chirped. “Can I have a lollypop?”

I dug in the diaper bag, wedged in the bottom of the stroller and produced a bag of treats. I handed him the bag. He considered his options and made his careful selection. Then he leaned up and tapped the sunglass-wearing man on the knee. 

“Would you like a lollypop?”

The man cocked his head to the side, dropping his glasses to his nose to check out the offer. He smiled just slightly, with only one side of his mouth. 

“Why yes, little man. I would like a lollypop.”

David handed him the bag of treats, which looked oddly out of scale in his huge paw. He picked one out and started to hand the bag back.

“Do your friend want one?” Davey asked. 

The man smiled again, using both sides of his mouth this time, showing bright white teeth and a gold incisor. 

“I’ll check. G!” he punctuated, elbowing his companion. “You want a lollypop?”

The friend grunted quietly, moving not a muscle. “Heck yeah I want a lollypop.”

He sat up and took the bag and made his choice, handing the rest back to my delighted boy. 

“What flavor you got? I has bubble gum.” Davey informed them. 

“Butterscotch,” said the first. “Sweet,” confirmed the second man. “I got cherry.”

They both sat up and chatted with him. Davey told them he loved Batman, they nodded their approval. Davey also told them his name is Davey, and that he had a big brother, that I was his mom, that we had been to the dentist and to the Lego store and that there were Batman Legos there. They nodded again, thick fingers twirling the thin white sticks in their mouths. 

Around us on the train, there was an almost imperceptible shift. Everyone in our immediate area smiled, taking on the scene. The lollypop bag was passed around to a few more people, who delighted in this small, unexpected treat. 

We all rode together for the next 10 minutes before we changed trains at Belmont to catch the Brown line the rest of the way home. When I informed Dave that this was our stop, he waved at his new friends and said good-bye. They nodded and twirled the lollypop sticks in their mouths in salute, “Bye D!” they called. Other passengers called out “Thank you!” and waved at us, wishing us a good afternoon. 

It was a very good day. 

And so it is in the spirt of friendship and our love of treats that we declare that August is the month of The Lollypop Project.We have stocked up on treats, and we are going to see how many lollypops we can give out this month on CTA buses and trains. Yeah, it’s technically against the rules to eat on there, but we are going to break this one in the name of lollypops. We’ll talk to a few strangers along the way and I’m hoping to share some of those stories here. 

 So if you see us, please enjoy a treat and we hope it makes you smile. Let’s see how this month goes. We hope it will be sweet.