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Related to miserably: errand, indicated
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(as) miserable as sin

Extremely unhappy, depressed, or wretched. Everyone just stood around looking miserable as sin during the ceremony. I felt as miserable as sin because of the breakup, but I was going to be best man at my brother's wedding, so I had to pick myself up and dust myself off.
See also: miserable, sin

(as) ugly as sin

Extremely visually displeasing or unattractive. This old car is all beat up and ugly as sin, but it's still going strong after all these years. I'm sure I looked as ugly as sin by that point, with my makeup smeared all over the place and my hair a total mess.
See also: sin, ugly

make (oneself) miserable

To cause oneself a great amount of stress, anxiety, sadness, etc. I don't understand why she keeps making herself miserable in a job she hates. She's just not interested in you romantically, Jack, so stop making yourself miserable pining over her!
See also: make, miserable

make life miserable for (one)

To cause one to be continually unhappy; to be a great and continuous source of stress for one. For some reason, the new manager seems to have decided to make life miserable for me. Don't worry, we'll make life miserable for them is they refuse to sign the contract.
See also: for, life, make, miserable
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.

make life miserable for someone

to give someone misery; to be a great nuisance to someone. This nagging backache is making life miserable for me. I wish you would stop making life miserable for me.
See also: for, life, make, miserable

make oneself miserable

to do things which cause one to be unhappy. You're just making yourself miserable by trying to do something you aren't qualified to do. I'm not making myself miserable! You're making me miserable.
See also: make, miserable
McGraw-Hill Dictionary of American Idioms and Phrasal Verbs. © 2002 by The McGraw-Hill Companies, Inc.

(as) miserable/ugly as ˈsin

(spoken) used to emphasize that somebody is very unhappy or ugly: He arrived at the party looking as miserable as sin.Some babies are as ugly as sin at that age.
See also: miserable, sin, ugly
Farlex Partner Idioms Dictionary © Farlex 2017
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References in periodicals archive ?
CEO of the Campaign Against Living Miserably (CALM), Simon Gunning, said: "We're hugely grateful to Andrew for his support of CALM.
Marriyum said that the government was furious because their NRO narrative had failed miserably and because they know they can never be half as good at governance and public service as Nawaz Sharif and Shehbaz Sharif.
"I was just hoping that I wouldn't fail miserably. It's vulnerable, you know, writing, co-writing, telling a story and directing it.
"Although under instruction from the party and coalition leader to mobilise the members to vote for the instruments that were coming before the House Mbadi failed miserably," Baya said in the letter dated September 25.
The recently elected chairmen have also miserably failed to resolve the core issues confronted by the citizens of these UCs.
Particularly, the current Afghan leadership has miserably failed to have good diplomatic relations with Pakistan, sabotaging the relationship further to the level of total collapse.
But on closer inspection it is clear that the Boundary Commission have snubbed Sutton Coldfield, have left it miserably underrepresented and clearly shown favour to Birmingham's inner city areas.
Now the Fianna Fail TD has accused the Government of "failing miserably" on its commitment to mental health services.
I'm sure it may be popular with visitors for the outside terraces which are lovely and the views over Birmingham, but as a library it fails miserably.
Attorney Preet Bharara, who has handled the Madoff case and conducted his investigation with the FBI, said at a news conference that JPMorgan "failed miserably" at its job as a bank and should have had "plenty of reasons to be uniquely suspicious" concerning Madoff's doings.
Fines and other deterrents have failed miserably and people's lives have been lost due to reckless driving.
What can we expect in the Middle East and why have the US overtures to the Arab/Persian world failed so miserably? A thought-provoking and informative article.
It took me 12 months to get the Inland Revenue to address me by that title, failed miserably with the passport office and I have yet to find a drop-down box with it listed.
Summary: Doreen Lawrence attacked the original police investigation into her son's murder, saying they "failed miserably" to find his killers.