an expression of joy in the success or good fortune of another combined with an expression of sympathy to someone who is experiencing pain arising from death, deep mental anguish, or misfortune.
Someone tells you they are having a baby but you are not sure that they meant/want to be pregnant: "I would like to offer my deepest condolulations"
by blamo54 December 18, 2012
Combination of "condolences" and "congratulations." Used in response to a statement or pronouncement where the user is unsure of how the person who made the statement feels about their statement or pronouncement.
by UncleWillard August 21, 2020