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Cougars

Cougar = older woman pursuing younger men
MILF = mom of your friend, classmate, etc.

Difference is perspective and initiative: 18-year-old Joey drooling over his bud's mom Susan is thinking MILF. 40-year-old Susan drooling over Joey is a Cougar.

(I don't think a woman's a true MILF unless she's the mom of someone your own generation. A 40-year-old man dating a 40-year-old single mom is not dating a MILF).

Why am I bothering to type this?
 
Cougar = older woman pursuing younger men
MILF = mom of your friend, classmate, etc.

Difference is perspective and initiative: 18-year-old Joey drooling over his bud's mom Susan is thinking MILF. 40-year-old Susan drooling over Joey is a Cougar.

(I don't think a woman's a true MILF unless she's the mom of someone your own generation. A 40-year-old man dating a 40-year-old single mom is not dating a MILF).

This is the basics of it, but there are a few intricacies you left out. MILF often refers to attractive women in their mid 30's to 50's even if it is unknown whether they are a mother or not (most women are by that point in their lives anyway).

Cougar more refers to the 40-59 age range. Unless otherwise stated, it can usually be assumed that that they are middle aged women desperately trying to hold onto their youth. Very often, they do this to compensate for the fact that they have not aged very well, and, IMO, are usually more creepy and pathetic then hot (unless you're into that kind of thing...). Think of the old ladies in the Producers, but 20 or 30 years younger.