My six-year-old son, Miles, has never been a huge fan of babysitters. When he was younger, he tolerated them, more or less, but as he grew older, his patience grew thinner and thinner until finally the day came when he would tolerate them no more.
Coincidentally, this full-blown babysitter rejection occurred at the same time that the third of his three siblings started school full-time and Miles was to be with a babysitter during a portion of the day alone, without a sibling buffer.
Now I work from home, so a babysitter for my small son was kind of a necessity. But Miles is a stubborn boy. He made it very clear that he didn’t want a babysitter and he stood by that sentiment. 
Over the course of several months, we went through a number of sitters. Anna, Julia, Amanda, Elizabeth – all smart, nice, pretty UNC students eager to engage Miles in conversation and play . . . and all systematically rejected. Some understood when I explained that Miles was going through a little phase and they should not take it personally. Others, well, took it personally. One even cried.
“I don’t understand,” she wailed. “I’ve been babysitting for years! Kids love me! But Miles, he won’t even give me a chance. He won’t let me read to him. He won’t let me play with him. He won’t even look at me.”
I tried to comfort the girl. “I’m so sorry. Trust me, it’s him, not you. It’s just a thing he’s going through. He’s decided that he despises all babysitters.”
“But I’m not all babysitters,” she sobbed. “I’m really, really trying . . . but I think he hates me.”
I nodded sympathetically. When Miles decides something, there isn’t a whole lot that’s going to change his mind.
Eventually, I just gave up on the babysitter idea for Miles and worked while he played quietly in the other room.
Now that Miles is in school full-time like his siblings, we don’t have a need for frequent daytime babysitters. Still, there is the occasional evening or morning that we need someone to help out. My other children love it when I hire a babysitter. They find the girls fun and entertaining and enthusiastically appreciative of my kids’ various projects. Miles, however, continues to remain aloof and suspicious.
Then we met Erica. Erica is a speech pathology graduate student at UNC. She is quiet, sweet, conscientious, and always prompt. But much more importantly, at least from Miles’s perspective, Erica has an iPad. And not just any iPad. This is an iPad that she allows Miles to play with.
When Erica purchased her iPad, she probably did so without the knowledge that this small technological marvel would elevate her to a status above all other previous sitters. But it did, and Miles has no issue at all when I tell him that Erica will be coming over. As long as I promise to remind her to bring that iPad of hers.
But graduate students do occasionally have things to do other than babysit my children and there have been two times this month that Erica was not available and I had to bring in an alternate, Ginny. Ginny, a graduate student in the same program as Erica. She is equally kind and sweet and fun. But unfortunately, Ginny does not have an iPad.
The first morning that she came to babysit, Miles told me that he would not interact with Ginny in any way while I was gone. He wouldn’t talk to her, he wouldn’t look at her, and he certainly wouldn’t allow her to look at him. In fact, Miles said he wouldn’t emerge from his room until she left the house.
Miles stuck to his guns. Ginny never once saw my youngest son. She had the other kids serve as messengers and check on Miles periodically.
Ginny babysat again the other morning and this time, Miles did decide to grace her with his presence. But that was the extent of it. He still wouldn’t talk to her or look at her or interact with her in any way. Well, at least we were making some progress.
I returned to the house hours later to find Ginny and the kids playing games and having a grand old time. When I stepped through the door, Miles immediately summoned me and motioned for me to bend down so he could whisper something in my ear.
“Mom,” he said in his quietest voice. “next time, you get this one again,” he said conspiratorially as he slyly glanced over in Ginny’s direction. He immediately slinked away to another room.
“Is everything okay?” Ginny asked me after Miles was gone.
“Pretty okay, it looks like,” I told her. “I don’t know how you won him over without an iPad, but congratulations! It appears that Miles just gave you the highest endorsement he would ever give to a babysitter. He is requesting you again, even without the expensive toy.” Finally, we hit the jackpot.