Congratulations offered to a co-worker who has just accepted a promotion that will certainly lead to misery.
Hey, Greg, my congratudolences on making division chief.
by colleraldamage2009 September 2, 2009
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The concatenation of "congratulations" & "condolences".
A conflicted expression of joy & sympathy in the success or good fortune of another whose fortune may also cause suffering, sorrow, misfortune, or grief.
"Well I am employed again."
"My congratudolences."
by ZUUL42 May 14, 2019
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What a poker champion would say to second place, because while second pays a lot of money, no one remember who finished second.

A term heard by Phil Hellmuth on The Raw Deal, unsure if he coined the phrase or was simply repeating it.
Final table, heads up, all in, Phil Hellmuth takes it down:

Miscellaneous player: "Wow what a ride, nice hit on the river Phil."

Phil Hellmuth: "Yeah you played a good game, Congratudolences!"
by FlushWithFlavor April 29, 2021
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When something is good happens..but has a downside.
Kevin: "Well, my mini retirement is over. I just got a job"

Karen: "congratudolences! At least you had some fun while it lasted"
by bobothedogboy May 31, 2019
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An exclamation of simultaneous praise and sympathy. What you would say to a person achieving a painful milestone.
Congratudolences on divorcing your husband who ran off with your sister!
by Buttwangu May 19, 2017
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Congratudolences is a combined word made from and expressing both congratulations and condolences at the same time, concerning the same issues and how that may be viewed as both a good thing, and a not so good thing.

Congratudolences is an idea brought to life by Katra Briel. Please use this handy and useful word. It helps express your understanding that some things in life are bittersweet and that those going through them at the time may need the encouragement of a positive step forward and the loss associated with some events we all go through at one time or another.
Congratudolences on your recent divorce, you're free now,and I know it hurts, but it's what is best for you.
by Faith Kendoll January 28, 2020
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