Entertainers often get requests from event organizers looking to book our services for a specific date, but often the request comes with a request to keep ourselves free for a rain date. As an an entertainer myself and someone who owns a business that supplies entertainers, it's my job to manage expectations and I spend a great deal of time explaining why we can't do that. So, if you are here, I'd like to think you have some interest in understanding why and I'm more than happy to explain.
First of all, most of the work requests we receive are during non-standard work hours. If you think about it, this makes complete sense. But what people often don't think about, is that face painters, balloon twisters, body artists, etc. must rely mostly on bookings Friday evenings, Saturdays and Sundays for their income. We only get paid when we are actually entertaining and those peak party times are fairly limited.
If you request a painter for a two hour event on a Saturday and ask that we hold a rain date on Sunday, you are asking the entertainer to block off a time period on two days for your event. I have yet to receive this request with an offer to pay for services on both days, so the entertainer would essentially be turning away paid bookings, for an event that may not occur. After being in this industry over 10 years, I've had this request often enough to know that it is actually not considered inappropriate. As a small business, I hope anyone reading this can appreciate that it is not something that any company can, or should be expected to do. I should also mention that I've also had requests, where a festival organizer contacted me to request a face painter, expected us to pay to be at the festival (which is fine), but they also expected us to hold a rain date. Yup... you read that right.
To draw a clear comparison, if you were planning an event and hired a caterer, would you ask them to keep both dates free? What if you hired a band? Would you ask a food truck to pay to be at an event but have them hold two days in case of rain?
So to sum up, if you are willing to pay for an entertainer for both party dates, I would be more than happy to work to secure an artist for those dates. Any other option is probably something more fitting for a volunteer and should be approached that way.
Thank you if you're still reading. Hopefully, this will resonate with someone which makes writing this post completely worthwhile. If not, I still got it out there, and yes, I feel better. ;)