How to find a good babysitter in Chicago: It’s not as easy as you think

Finding a good, responsible babysitter is pretty hard to come by. Being able to have another parent or adult vouch for said babysitter is even harder. Discovering a babysitter who lives nearby, drives, knows the Heimlich Maneuver, CPR, proper EpiPen administration, doesn’t have a skeezy boyfriend that will sneak over and eat all your snacks, and you can actually afford is like finding the Holy Grail.

When you do find someone who might be a perfect match for your family, it is as awkward as asking for that first date. You’re wrought with all of the same self doubt and are totally afraid of rejection.

What if the babysitter is taken? You don’t want to break the cardinal rule among parents which is: “Don’t steal thy babysitter.” What if the babysitter doesn’t think your kids are cute? What if the babysitter doesn’t have the same schedule as we do? What if the babysitter thinks we are weird or something?

Sure, I could look for a babysitter via those internet matching sites, but call me old fashioned, I just don’t trust them. What happened to the good old days of friends matching you up or meeting a nice babysitter through church or work?

Despite the insecurities, and the internet, let’s say you gather up enough courage to ask for the potential babysitter’s number. Now what? How soon is too soon to call? Or do you text? Do you wait a week? Two weeks? Seriously, do I text?

And what about deciding if the babysitter is a good match? Do we have a first date scenario, as in my husband and I go on the first date we’ve been on in months while the babysitter and kids get to know each other? Do we have like a meet and greet, where we stay home and we introduce the babysitter to the kids? And what about appearance? Do you keep it real? Or do you try and woo the babysitter by cleaning your house, bathing the kids, stocking the fridge and cupboards with good snacks, renting movies and telling everyone to behave (because for the love of all that is holy you need a night out)?

Let’s say the babysitter is great, but she’s just not that into you. You’re a little heartbroken, but you know you have to move on. The babysitter has scheduling conflicts or has other things going on. Now what? How do you ask her the babysitter about friends or siblings without it seeming awkward?

And again, how soon is too soon to call? Or should I text?

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