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Phrase(s): Faint heart never won fair lady.
Prov. A timid suitor never won his lady. (Used to encourage boys or men to be bold in courting women.) • Bill: I’d really like to go out with Alice, but what if she says no? Alan: You won’t know till you ask her. Faint heart never won fair lady. • Don’t be so shy about talking to Edith. Faint heart never won fair lady.
McGrawhill's American Idioms And Phrasal Verbs