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Dear Dana: The SmartSitting Advice Column: Help! I’ve never had a babysitter before!


Dear Dana,

My daughter is 16 months old and I have never had a sitter before. If you count the last month or two of my pregnancy, there has not been a date night in this house in over a year and a half. 

I know I need to get comfortable with having someone else care for her besides myself and my immediate family, but I’m just not sure how to act around a babysitter. I feel like I’ll either give them way too much information or not enough, or I’ll just check in constantly – at which point, why do I even have a babysitter?! I’ve signed up for babysitting sites and looked at profiles before but I always get overwhelmed and give up. How do I get over this and get out? 


Nervous Mama


Dear Nervous Mama,

I can’t tell you how familiar your story is to us! Needless to say, you are not alone. Leaving your sweet little one with a brand new person for the first time can be very overwhelming indeed. Like you said, there’s so much to think about that it’s hard to know where to start, and all that worrying could ruin your date night before it has even begun.

Here’s the thing: you will be nervous the first time you leave her, and that’s okay! This is a perfectly natural feeling. The best thing to do is to take – quite literally – “baby” steps.

Looking through profiles for your very first babysitter is overwhelming because there are way too many of them and it’s hard get a sense of someone from an online profile. Whenever possible, use a personal source (a friend, a local moms’ group, or a reputable child care agency that takes references and can share them with you). Regardless of how you go about it, take your time with the process. That first babysitting booking doesn’t have to be a whole night out with someone you just met sitting in your home. In fact, you don’t even have to leave the house! It’s very common to do a “test run” with potential new babysitters, where you would be home the whole time, watching how they interact with your baby, talking to them about their experience, and seeing if you feel that trusting connection that’s so important to have with anyone taking care of your little one. 

If you don’t feel assured… that’s okay. Identify the source of your hesitation. Do you need a babysitter with a different energy or child care style? Perhaps a babysitter with more child care experience? Maybe just someone with more life experience in general? Would it make you feel better to speak with a reference that knows this babysitter very well? Whatever the answer is, once you know it, use it to keep moving forward!

Once you do feel comfortable with someone… lock down a few upcoming days that they’re free and you can use some babysitting. Maybe the first time you leave will just be to run an errand around the corner and come back. The next time, maybe you grab coffee with a friend in your neighborhood. Soon enough, you’ll be back out on the town for that long-awaited date night, and you’ll be able to relax and enjoy it, knowing your baby is in familiar and capable hands. Why not even lock in a few dates at once? One of the biggest frustrations is finding someone you like and not being able to line up your schedules, so planning in advance is important!

Once again, taking your time is totally okay as long as you’re still making progress. Embrace this next step in your life as a parent AND an individual, and don’t be afraid to be honest with your babysitter! You can say to them, “You should know that you’ll be our first babysitter. I’m feeling nervous, and I’d love to talk through my worries with you. If I seem untrusting, I assure you it’s not personal!” Most will have been someone’s first ever babysitter at one point or another, and the right person will be kind and understanding about all your concerns.

You can also ask them to send occasional photo and text updates while you’re out to make sure you know what’s going on at home. Those little photos can be very helpful in putting you at ease! Here’s one Suzie, our Director of Operations, recently got from her babysitter:

“Someone got into the clean laundry!”

first time babysitter toddler


Good luck, and make sure to write back and let us know how it’ s going!

Yours Truly,



Dear Dana is SmartSitting’s advice column for parents, nannies, and babysitters in NYC. Dana joined SmartSitting in 2012 as a full-time nanny. She worked with the same Brooklyn family for over three years, and she still adores them and sees them all the time. Since then, Dana has worked with countless other families with children of all ages. For the past year and a half, she has also worked in the SmartSitting office in a variety of roles. She speaks with families, interviews babysitters, writes for our social media accounts, and continues to babysit to this day. Dear Dana is a collaboration of her experience with the perspectives of our other client directors, who are also previous caregivers and current parents. To submit a childcare-related question to Dear Dana, please email dana@smartsitting.com. We can’t wait to hear from you! 

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