When deciding whether or not to send someone a funny gift, consider the following two things in order to avoid potentially embarrassing your receiver. First and most importantly, consider your relationship with the recipient in judging the appropriateness of your humor. A secretary, for example, should not give her married boss a suggestive gift on the occasion of his retirement, and likewise, a boss should not give his secretary such a gift in recognition of her tenth anniversary with the firm. Second, consider the occasion, and err on the side of conservatism whenever doubt exists as to whether or not it calls for humor. It is never appropriate, for example, to give a gag gift to a bride or groom on their wedding day, nor is ever acceptable to send a card or gift that makes fun of something personal such as a persons appearance, health or age.
Unless you are absolutely positive of the recipients sense of humor, it is better, as a rule, not to send gifts that are humorous if theres a chance they might offend. If you simply cannot resist the temptation to yuk it up at your friends expense, practice at least some degree of restraint in choosing the gift by keeping a...