Any application which uses passwords should also have a field for "password hint". This I think will encourage people to use different passwords for different services. (People should of course make their password hint fairly obscure so as not to aid others guessing. This seems to be an art.)
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But I like to imagine that the who are people careful and security-conscious enough to not reuse passwords will go the extra step of simply using very strong long truly random sequences of characters stored in a password manager for almost all of their passwords, instead of trying to remember all their passwords... :)
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