I really want to say it depends on the nature of the relationship and what you are expecting.

The woman that I dated that were older found me attractive and interesting and sex was good, but when it came to position in life I fell short.

I think one problem that I have recently experienced is expectation. The woman I dated never was married and had a very black and white view of relationships. She felt or thought in a certain way then she believed the other might also. She had an idealistic view of relationships and believed in total and complete honesty early in the relationship, but I argued if we gave people we were interested in complete honesty than nobody would be dating anybody and we would be busy telling each other that we weren't interested (I never pointed out that she weighed 50 extra pounds in person than her picture she sent me - I really think I would have
F%@#ed myself for being completely honest with her about that - but that might have been viewed by her as a double standard for me to call that out about her. I held back and didn't say anything because I would have been viewed as superficial or shallow).

I think the age difference made it difficult to explain things to her or for her to listen to me. I am so glad I am done with that.

I think deep down inside young or old we are all messed up. If you guys like each other, can have stimulating conversation, keep your assets separate (no money lending) and have wild monkey sex that curls your feet than go for it!

Go get him cougar!