Cryptic crossword clue
In contact with uppish maid, was flirting 5

The most common and most likely answer to this crossword clue is the 5 letter word TOYED

T
O
Y
E
D

Buddy explains!

The straight part
We know that "was flirting" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case was flirting = toyed.
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.

What does TOYED mean?

TOYED verb
  1. To play (with) in an idle or desultory way.
  2. To ponder or consider.
  3. To stimulate with a sex toy.

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