The most common and most likely answer to this crossword clue is the 5 letter word ASHER
I've seen this crossword clue in The Guardian
A
S
H
E
R
Buddy explains!
The straight part
We know that "Jane who went out with Paul?" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case jane who went out with paul? = asher.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.