Conversation so far:
Was Bob Hope still working in his later years?
Bob Hope continued an active entertainment career past his 75th birthday, concentrating on his television specials and USO tours.
What year did bob Hope star with Dolores Reade in the musical Roberta?
in 1933

Question: Did he have any kind of personal relationship with her?
Self-contained rewrite: Did bob Hope have any kind of personal relationship with Dolores reade?