In an ideal world, which this clearly is not, you give gifts because you want to find some tangible way of expressing your love or affection, or of marking some occasion for someone that is important to you.

As a general rule, cash is not an appropriate gift, as the whole point of gift giving is to show how in tune you are with the needs and wants of the recipient – at its best, a gift is a sharing of a mutual interest, or at least an insightful recognition into the values of the recipient. The key rule of gift giving is that you are not buying for yourself, but for the recipient, and you must step outside of our own desires to think about what someone else would enjoy. This exercise is very useful, as most people, most of the time, give very little thought to anyone else’s desires, and a great deal to their own. Buying a gift may even expose you to worlds of which you were previously unaware. This is often the case when men shop for women, and vice-versa. He knows little about spa treatments, and might care even less. But, knowing that she cares a great deal, he might well go outside his normal comfort zone to learn something about the endless permutations of massages, facials, and pedicures.

Cash gifts are for lazy givers, and recipients who know that the gift is coming from someone who really doesn’t understand their wants and desires. With a cash gift, you are basically telling the recipient that you don’t know what they would really like, don’t feel like figuring it out, and mostly don’t care. A recipient who asks for a cash gift is saying that they don’t expect the giver to be able to make a good judgment as to what they would like, and, really, they know what they want, so just let us buy it ourselves – but that takes the thought out of the process, and reduces it to a simple asset transfer from giver to recipient.

When is a gift appropriate? Whenever you sincerely wish to give one. A gift is not appropriate as an attempt to influence someone, which is why people distinguish between gifts and bribes. What you should hope is that the recipient really enjoys it, and appreciates the effort you took to identify such a thoughtful gift. Even if the gift is not especially appropriate, the recipient should appreciate that the giver gave it the old college try. It’s also important that the gift benefit the recipient; when a man gives a woman lingerie, he is giving himself a gift.

When should you expect a gift? As an adult, almost never. Many people don’t want gifts, as they are embarrassed by them, or don’t like the routine of obligatory play acting and appreciation that is part of the gift giving process (and which can be avoided by giving gifts in person, but opening them in private). If someone does not wish to receive gifts, on any occasion, they should plainly state their preference: “No gifts please” means just that. “Gifts optional” means that the recipient is expecting a gift. “Cash Tree” means you won’t be getting anything from me.

As for wedding gifts, you should give only if you attend the festivities, or if the person is so close to you, as in your brother or sister, that they would have a legitimate right to feel offended if you did not give a gift. Some use their wedding as an excuse to troll for gifts, by sending invitations to people living in Borneo, thinking that they won’t come, but might send a gift. If you happen to receive such an invitation by all means just ignore it; or shock the happy couple by actually showing up.

Gifts should only be exchanged among family members if all parties to the exchange are willing and able; family gift exchanges often become a chore and a bore. In most families, some members will be much more affluent than others; if it’s a real financial strain for any member of the family to purchase gifts, than exchanges should be avoided. As a general rule, the value of gifts should be limited to the amount that all parties can easily afford. If the richer siblings spend more than the poorer ones, it’s easy for the latter to be embarrassed and shamed by their relative poverty. On the other hand, the poorer members of the family should not view holidays as an opportunity to socialize assets by accepting far more than they give.

There are lots of classy gifts that don’t cost a lot, whether you’re buying for family, business, or friends. For the manly man who enjoys the occasional cigar, a very adequate one can be purchased for $5, a very fine one can be had for less than $10, and a truly extravagant cigar for less than $20. Give just one, or several, depending on your budget. A great book can change someone’s life, and can be purchased for less than $20. A caution here though – don’t give a book to someone who is not a regular book reader, and choose very carefully, again remembering that you need to have their interests, not yours, at heart when making the selection. If shopping for a guy, refer to our manly list of books and movies for help.

If you know that someone likes a drink, a very nice bottle of wine can be purchased for less than $20, and champagne is always a good choice around the holidays or when celebrating a special occasion. You don’t have to go super high end here, and the recipient, unless a true connoisseur, will usually not be able to tell the difference in taste between a $20 and a $100 bottle, although they will notice the brand name. But don’t go low end; there’s something tawdry about cheap champagne.

One of these relatively small gifts, especially wine or champagne, is often a nice touch when visiting someone’s house for the first time, or going to dinner at a friend’s house, or just as a thank you for some favor or consideration. Of course, you’ll show your thoughtfulness by avoiding alcohol for those on the 12 step program.

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