The hallmark of the compleat punster is the ability to work puns into real-life situations - and to do so in an appropriate, natural and spontaneous way. Unless one is skilled at ad-libbing, it's best to have a repertoire of material to draw upon. Your objective is to be regarded as clever and witty rather than irritating. But opinions may differ.
""Did You Just Make That Up?" Puns in Everyday Conversation,"
Word Ways: Vol. 39
, Article 12.
Available at: http://digitalcommons.butler.edu/wordways/vol39/iss1/12