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Parent interactions with teenage babysitters are inherently awkward, all the more so when it’s a dad returning home to a young woman he’s never met before. This was exactly the scenario that occurred on the evening in question. My wife, at the time a college professor, had hired a student from her University to man the fort while we both had evening work commitments. I went directly from my office to my meeting and therefore hadn’t met the babysitter prior to coming home before my wife that night.

I walked in the house, quickly introduced myself and quickly followed up with “can I Venmo you?” Like most folks these days, I rarely have cash on me. I also assumed a college student would not be interested in being paid by check and, most importantly, would be familiar with the increasingly ubiquitous Venmo payment app such that it could be utilized as a verb.

Boy was I mistaken. The horrified look on the babysitter’s face made it abundantly clear that she was both unfamiliar with the app and extremely concerned about the meaning of the “verb” I had used.

I explained about the app in a panicked fashion, but the damage was done. I think I wound up paying her double her fee, apologizing profusely as I wrote her a check. When my wife came home, I informed her that there was a 0% percent chance the student would ever babysit for us again before telling her what had happened. My complete and utter embarrassment made the story very amusing to her.

As I recounted the story shortly thereafter to a friend, he told me I had dodged a bullet because it could have gone even worse. Confused, I asked him what he meant and he said, just imagine how much more awkward it would have been had she responded by saying something to the effect of “sounds exciting, let’s do it before your wife gets home.” I think I would have just turned around and walked back out of the house until my wife came home.

Fast forward a few weeks to the next time we hired a babysitter. This time my wife and I returned home from dinner together but, nonetheless, I was determined to avoid any semblance of a repeat occurrence. I pulled up a chair and sat down across from the babysitter before asking her in a very formal manner if she was familiar with the peer-to-peer payment app called Venmo and if I could utilize it to compensate her for her babysitting services. She looked at me like I was crazy and said “so you want to Venmo me? Sure.” Awkwardness begets awkwardness but I felt somewhat vindicated by her response, despite the fact that she was looking at me like I had four heads.

I now take the less dangerous and (hopefully) less awkward approach by asking babysitters if they use Venmo before inquiring about paying them via the app. If nothing else, I’ve gotten many laughs out of friends and family by recounting the story.

Do you have an embarrassing but funny parenting story? Please share it with me below in the comments or on Twitter, where I’m @DadLifeStories. Thanks for reading!