Weirdly (or not, perhaps) MILF Island was turned into a real show (sort of) not once but twice. On The Cougar a 40-year-old woman was seeking a partner among male contestants who were all in their 20s. On the rather more disturbing MILF Manor a group of women between the ages of 40-60 stay in a villa seeking to pair up with a pool of younger bachelors, which turns out to be made entirely of the women’s sons. Wikipedia says in season 2 the ex-husbands were also added to the dating pool so the sons had to compete against their dads for the divorced moms.
John Oliver sometimes runs random out of context clips of MILF Manor and I'm not sure actually watching them in context would make them any less ridiculous.
I only saw a promo for it once and was pretty grossed-out, but had to at least look up the Wikipedia. I don’t think I was the target audience, other than it reminding me of 30 Rock.