Phrases Phrases for Handling Awkward Situations

I should have...

B1

Meaning

I regret that I did/didn't do something.

Example sentences

John: Why are you so upset?

Alice: I missed the deadline for the project. I should have started it sooner.

John: It happens. Don't beat yourself up too much.

Alice: I know, but I really messed up. I should have been more organized.