Can’t remember movie name

Hi I’m looking for the name of a movie that I think may have been on Netflix or prime, it’s an American based movie that’s maybe based in the 50s or 60s where a you newspaper writer or journalist travels America with new friends, in one scene his friend invites him to join him having sex with a girl, one off his friends has a child with a girl and she doesn’t want him around, towards the end of the movie he is walking outside his office only to find his old friend that is homeless in San Francisco