Hi Stuart,
Brilliant! No need for snacks or chaperon, MUA or a hairstylist, so what works! The idea of the bald head is not quite clear enough but with your title it works enough to be funny. I did smile, in fact I'm smiling again right now, even after seeing Leonardo's gross head! His also didn't have a MUA or hairdresser!
I feel that the picture is too flat perhaps. You have not used light to amplify the importance of the lady. The soft out-of-focus bush is distracting. If there was a wider field with more of the foliage, then it might not matter if the leaves were soft. however, they should not be blown in the shiny highlights. I suggest underexposing for outside but using strobe for the lady.
Shooting much wider might give the lady at the window more context. I like the project and hope this is accessible for you to work further on this fun idea.
Asher