I remember watching it when i was still in middle school so probably around 2004, and I only remember two scenes , which i guess isn't really helpful. It seemed sort of like a bay watch movie? if that makes sense. the first is, is a girl who's a babysitter and shes dressed in an afro wig and a boy comes in and she takes off the wig and starts making out with him???? -_- the second scene is a guy talking about his deceased wife with a much younger teenager girl, and starts to unzip her bathing suit in a hot tub. Yeah I'm sorry if this doesn't make any sense but if you remember these scenes somewhere it would be great!!!! thank you :)
There is some similarity in "The Babysitter" (1995), However I cannot remember a wig worn by the babysitter. She does have a boyfriend that sneaked in and later the man whom she is babysitting for comes in drunk and tries to take advantage of her.