Giving gifts, like all sports, involves certain rules. If you aren't playing by these rules you are playing some other sport and this post may not apply to you.
The basic rules of gift giving are as follows:
1. You are obligated by your family, social and professional relationships to other people to give them gifts at agreed upon times which are a function of the identity of of giver and receiver of the gifts. These occasions for people with a Christian heritage in the United States typically include birthdays and Christmas.
2. The value of a gift given should be commensurate to the magnitude of the occasion, your relative social positions, and your affluence. More important events call for bigger gifts, closer relationships call for bigger gifts, gifts values should reciprocate and calibrate past histories of gift giving between you, in unequal relationships the superior person is expected to give a larger gift than the inferior person, gifts should not be beyond the means of the giver, and gifts should attempt to make less affluent recipients materially better off but not even attempt this task for more affluent recipients.
3. The more a recipient likes a gift received, the better.
4. Gifts of money are strongly discouraged except from relatives who don't interact daily with the children who receive them (e.g. out of town grandparents to grandchildren), and from recipients of services to providers of services (e.g. household service providers and newspaper deliverers). Gift cards are superior to money, but still in the same class of gifts as money.
5. Potential recipients of gifts are allowed to hint, ideally as subtly as possible, about possible gifts or material desires, but are strongly discouraged from asking for a particular gift (unless they are young children), or participating in the selection of their own gifts.
6. Lower quality and less costly gifts that reflect the personal efforts of the gift giver are comparable in value to more perfect, more valueable gifts purchased from a store. Intermediate between these two extreme are gifts purchased from a source that is not readily available to the general public -- a quirky botique, for example, rather than a brand name product from a national department store chain.
7. It is improper to publicly admit that someone has given a bad gift, but is entirely proper to note this fact with discretion in private. The disappointment of the recipient and the private discussion of the giver's poor gift giving skills are the only penalties for failing to give good gifts, but over time the cumulative effects of these penalties can be significant and reflect on the gift giver's character.
These rules only make sense when you realize that the heart of the sport of gift giving is not really about transferring wealth. Gift giving is more anthropology than economics. It is a form of symbolic communication. Its purpose is to test the gift givers awareness of his or her social obligations, of the nature of his or her relationships to others, and of his or her empathetic understanding of the wants and desires of people who are part of his or her life.
Giving appropriate and appreciated gifts is a way to indicate that you understand the people around you personally, and also understand the cultural context in which all of you are embedded. It is proof of high emotional and social intelligence.
In contrast, a failure to give socially expected gifts, giving gifts when they are not called for socially, giving gifts that are either too high or too low in value for the recipient from the gift giver, or giving gifts that the recipient does not value demonstrate that the person giving the gift is socially inept, and thus reflects poorly on that person's character, unless there is a good reason for that person to be socially inept.
The routine process of gift giving also identifies for the recipient and those who observe the gift giving taking place, social miscues that are taking place so that miscommunication can be clarified. For example, if a woman receives diamond jewelry from a man from whom she had expected to receive a cute coffee mug, she knows that the man sees their relationship differently than she does.
The sport of gift giving is, by design, notoriously difficult to execute properly on a consistent basis, despite the relatively straight forward rules. As is the case of a batter in a game of baseball, outright failure and near misses are normal and expected, while home runs are rare for all but the truly excellent. This is important to the sport because its purpose, much like an IQ test, is to evaluate the relative social graces of the participants in the sport. If it were too easy, the sport could not adequately distinguish between the many fine gradations from profoundly graceful to socially inept. This ranking in addition to exposing miscommunication, also serves to identify who is and is not capable of engaging in delicate social tasks in the future. Inept gift givers are poor candidates for preparing seating charts for a wedding, for example.