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congratudolences 

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."
congratudolences by ZUUL42 May 13, 2019

Congratudolences 

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!

congratudolences 

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"

Congratudolences 

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.
Congratudolences by Faith Kendoll January 27, 2020

Congratudolences 

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!"

Congradudolences 

noun

1. The act of congradudolating

2. Expression of joy and perfunctory sympathy on the death of a horrible and miserly parent-in-law, (usually father) especially when a fortune has been inherited.

interrogation

3. congradudolences ? ( used on the passing of an unpopular relative when the size of inheritance is not known)
Congradudolences bro, that monster in-law's penthouse will be pretty sweet
Congradudolences by bestia March 5, 2015