Brad was 41 when he went for Jolie. In general if you are an intelligent human being you detect crazy no matter how attractive at that age. An affair sure but never marry or have kids . With Jolie the warning signs were all over the place even back then that she is a narcicistic trouble maker in true hollywood fashion.
I dont mock Pitt for this. Its deeply tragic to have kids with such a woman that will estrange them from their father. Thats a huge scar for life and no fame or wealth can fix this.
So to answer. At that age most intelligent men will go for Aniston (if she is more down to earth I know nothing about her) but possible have an affair with Jolie.
Personally I never got why Jolie is supposed to be so attractive. She had cosmetic surgery all over her face even at that young age with absurd injected rubber lips. But everyone talked about that being "natural".

Her acting and behaviour outside of it was just pure self obsessed shallow personality.
Her UN "job" is the perfect example. She gives exceptional dumb statements showing that she has zero clue about politics and history in general loves the attention of being a "special envoy to the UN high comissioner". She is a walking Duning Kruger effect.
Remind you the most horrible people often hide behind charity work . Its the perfect mask, feeds their ego and hides their nature. Jimmy Saville being the perfect example. Or take Bill Gates being a close Epstein friend.