This story happened quite a while ago when I was dating a woman who had a young son. I wouldn’t call her poor as she had enough to survive, but she did have to live on a careful budget, and this meant she couldn’t afford a babysitter so we could go out on a date alone often. I offered to pay for one, but she was adamant about paying her own way and didn’t seem comfortable taking me up on the offer.
Then, one day, she called to set up a date on Friday.
Girlfriend: “I found a babysitter, and I can’t wait to try her out! She’s thirteen or fourteen, and she put little homemade fliers in the mailboxes of all the people in the neighborhood with kids. She has an offer to do the first babysitting job — up to four hours’ worth — for free, and for any jobs after that one, parents can pay what they feel is appropriate.”
I was a little uncertain about her using someone she hadn’t met personally; I didn’t have much experience with kids yet but [Babysitter] seemed too young to be trusted to babysit already. However, [Girlfriend] insisted another local mother who used the babysitter said she was amazing. Plus, [Girlfriend] had spoken to her over the phone for a while and she sounded mature and responsible and had been trained in CPR and first aid.
[Girlfriend]’s enthusiasm over this new babysitter dried up, though, when she opened the door to find a young man, not the girl she kept referring to, on the other side. It seems [Girlfriend] had presumed the babysitter was a girl but had never thought to ask. He had a gender-neutral name, one that I associate more with females but that wasn’t that odd to have been given to a male, either. When asked about the phone call, he apologized for any confusion and explained that he was often told he sounded feminine on the phone.
[Girlfriend] was clearly having second thoughts the moment she realized the babysitter she hired was male. She lingered, repeating emergency procedures and bedtime routines while clearly being hesitant to leave the teen and her son. In that time, [Babysitter] introduced himself to [Girlfriend]’s son and in record time got the kid to open up and start playing, which impressed me since I knew from personal experience that [Son] could be quite shy around new people. Seeing that [Babysitter] seemed to know what he was doing, I finally convinced [Girlfriend] to leave the two alone so we could go on our date.
She was still worrying about [Babysitter] at the start of our date. Ironically, that left me needing to assure her that the person I’d originally been a little less confident in seemed to be getting along great with her son and everything would be fine.
When we finally got home, [Girlfriend]’s son was alive and well, already tucked away asleep in bed. The house was actually cleaner than we left it, with some of the kid’s toys that had been scattered around the living room put away. As to [Babysitter] himself, he was busy with the diabolical task of completing his homework.
My wife tried to offer him some money as he left.
Babysitter: “No, ma’am. Remember? My flier offers your first job free, and I don’t want to break a promise. But I’ll be happy to accept whatever you think is reasonable the next time you need me.”
[Girlfriend] hadn’t thought there would be a next time, except that the next day [Son] bombarded her with excited stories of the fun he’d had the night before and insisted that he couldn’t wait to be babysat by [Babysitter] again. I think that’s what finally forced [Girlfriend] to realize she had been unfair to the teen and accept that he was just as good a babysitter as advertised. She invited him back for future dates after that, to the excitement of her son. It didn’t hurt that he was willing to accept a very cheap fee for babysitting which made it possible for us to go on more dates alone.
In the end, [Babysitter] babysat [Son] for years, and then he came back to babysit our daughter once [Girlfriend] and I eventually married and had children of our own. He only got to babysit our youngest son a few times before he left for college, but all three children adored him.
In all these years with him babysitting for us, I got to talk to him some and learn a bit more of the story behind the first babysitting job. My wife’s original presumption that he was a girl wasn’t entirely her fault, after all. He had intentionally modified the quotes on the flier he had passed out to replace any pronouns with his name to hide his sex because he had learned that people were less likely to choose him if they knew he was male. Though, he insists he never lied and that his voice did naturally sound female on the phone.
This was also why he offered the first babysitting job free: to hopefully get his foot in the door and convince parents they could trust him with their children. Plus, he simply liked kids and didn’t mind babysitting, even when it was free. As to his “pay what you want” policy, he claims that most people paid him very well when asked what they thought was reasonable, possibly better than he would have gotten if he’d just named a price.
[Girlfriend] was one of a few he knew were underpaying him, but he could tell she had a limited budget, and he was okay with accepting what she could afford — even if it was less than others offered — to help her out.
Of course, once we got married and my wife finally would accept my chipping in financially, I insisted that we pay him a better rate for his time babysitting for us.
