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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.
(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.
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!
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.
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.
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.
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.
Farlex Partner Idioms Dictionary © Farlex 2017