Bonding Through Babysitting

June 2021

by anna rogers & livy jensen | photos by arianna skoog

A dual perspective by a mom and teen babysitter on creating healthy, trusting, and lasting relationships between babysitter and family. 

Good babysitters are like gold. They come into our homes and give parents the greatest gift: time. They enable date nights, work catch-ups, self-care, time away with friends, and much more. Babysitters are entrusted with our greatest gifts – our children. They are nurturing, feeding, engaging, and pouring into the lives of our kids.  

As parents, are we undervaluing our babysitting relationships? Are we viewing those much-needed hours away as a casual quick gig or as an opportunity to connect and build a trust-filled relationship with those who tend our most precious treasures?  

We know that fruitful relationships are always a two-way street marked by communication, transparency, and mutual respect. Relationships with our babysitters are no different. When we cultivate a healthy relationship between parents and babysitter, everyone wins (especially the kids).  


Hi! I’m Livy. I started my babysitting days when I was 11. I started off by taking the Billings Clinic Babysitting Course, where I received CPR certification and learned many other first aid and general safety skills.  

Easing In 

It's important when you first start babysitting to watch kids in short increments of time and with a familiar family. This could mean offering to watch your neighbors’ kid while they make a run to the grocery store or letting the parent get some work done at their house while you watch their kids. This makes it so much easier to ask questions and familiarize yourself with their house, kids, and expectations.  


As you move on to longer spans of time, make sure that you set your own boundaries as far as how late you are comfortable staying, if you need help with rides, and what appliances around the house you can use. When I go over to a house, I expect that parents will be home at the agreed-upon time unless they communicate otherwise. The same should be expected of babysitters. If you are going to a new house, arrive 10 minutes early so that you can get a rundown of everything you might need to know: bedtimes, routines, kids’ names, expectations, meals, and parent information. Building long-term relationships with everyone is important to the whole dynamic of babysitter and family. Trust is key. 


There are a lot of fun parts about babysitting, including activities! Diverse and fun activities are a great way to keep everyone engaged and having fun. This also helps you get to know the kids and their preferences and personalities better. Leaning on your own skills or interests is a great place to start when planning activities. I really enjoy cooking and baking, so I make sure to include them in the time I spend with kids. Other activities can include “I Spy” nature walks, board games, reading, coloring, imaginary games, and art projects. Kids tend to have the best imagination when it comes to activities and games, so make sure you include them in this thought process as well.   

My final advice is to make sure that you have fun and create good relationships with families in your community! 


I'm a mom of two young children, and I work part-time from home. I spent a lot of time babysitting in high school and college and always valued building meaningful relationships with the families whose children I watched. Now, as a mom, it's incredibly important to me to have a healthy relationship with the wonderful babysitters who come watch our children.  

Easing In 

I always seek out a babysitter who is either the child of a friend or a friend's friend. Having a trusted recommendation or knowledge of the individual ahead of time is an important foundation. When starting with a new sitter, especially someone who is on the younger side, we always start with a daytime gig while I work in a room of our house or a quick afternoon date on the weekend. This is as much for their benefit as for ours – we want them to feel safe and comfortable in our home and with our kids before we leave for longer periods or at night. 


Moms are always anticipating needs. Knowing what our kids need to be content and to thrive is woven into our nature, but we can’t expect a babysitter (especially early on in the relationship) to share our intuition. For babies and toddlers, an easy-to-follow written note is best. As kids get older, verbal communication will usually suffice.  

Ask questions to get an idea of what your sitter is comfortable handling so that you aren't putting them in a situation where they feel nervous or ill-equipped. Cooking meals, setting up strollers, and similar situations may require a quick tutorial. 

When prepping for a sitter’s arrival, take some time to prep your kids. Clearly communicate your expectations for respectful behavior and helpfulness. This step is key! Poor behavior and attitudes from children can drive away great babysitters. 


The way a sitter engages my children is the trait I value most. While I want them to be competent at navigating our home, behavioral issues, and getting the kids to bed, I really want them to make babysitting a fun experience for our children. A babysitter who takes kids outside, reads and tells stories, builds forts, and laughs with my children is a coveted and precious gift.  

Local Babysitter Courses 

BLAST!-Babysitter Lessons And Safety Training at Billings Clinic 

  • Ages 10 to 13, endorsed by the American Academy of Pediatrics 

Child and Babysitting Safety at the Billings YMCA 

  • Ages 11-15, with fundamental information on proper supervision, basic caregiving skills, and responding properly to ill or injured children or infants. 

Online Babysitting & Child Care Classes through American Red Cross 

  • Digital certification at your own pace. 

Originally printed in the June 2021 issue of Simply Local Magazine

Never miss an issue, check out SLM's digital editions here!  

Livy Jensen is a student at Billings West High School who enjoys baking, cooking, babysitting, watching movies, rock climbing, and thrifting.   

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