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Answer:
SHOULDA
Possible questions:
Ought to have, informally
we know 1 Answer
Slangy word of regret
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Part of a rhyming rueful triumvirate
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Ought to have, in slang
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One of three rhyming words of regret
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"Love ___ Brought You Home" (Toni Braxton's first solo hit)
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SHOWINGSHOWERS
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SHOTBY
SHOPPINGSPRAY
SHOED
SHOWMANCE
SHOTE