What’s a mistake you made that you should have avoided?, Is there a book you should have read but never did?, What’s something you should have told someone before it was too late?, Do you think you should have studied a different subject at university?, Have you ever felt like you should have apologized to someone but didn’t?, What’s something you should have done yesterday but forgot?, Do you think people should have been more careful during the pandemic?, Has there ever been a time when you should have spoken up but remained silent?, What’s a financial decision you should have made earlier in life?, If you could go back in time, what’s one thing you should have done differently?, Is there a job opportunity you could have taken but didn’t?, What’s a place you could have visited last year but didn’t?, Have you ever felt like you could have worked harder for something?, Do you think you could have been more successful in school?, What’s a life-changing decision that could have gone differently for you?, Have you ever been in a situation where you could have helped someone but didn’t?, Is there a hobby you could have started earlier in life?, What’s something you could have said to someone to change a situation?, Have you ever regretted not taking a risk you could have taken?, Looking back, is there a moment when you could have made a better choice?.

Should have / Could have

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