15 Tips For Dating an Older Woman: 1. First, Decide Which Type Of Cougar You Want To Date Yep, there isn’t just one type of cougar. In my experience, there are actually two types: Alpha cougars Beta cougars Your average alpha cougar is a sophisticated, classy woman who’s pretty damn street-smart. She’s intelligent, witty, ambitious, has a good career, and doesn’t need a man. Think Sex.