ALT-2 What to Give someone Who’s already quite well off
We give gifts for a variety of reasons. Sometimes they are given as a gesture of appreciation or as a way of extending an olive branch toward a friendship. At other times, they are given to commemorate a milestone or as a form of encouragement. But, most of the time, gifts are given to celebrate a significant or private moment between two people that care deeply for one another and wish to acknowledge that fact to each other.
Not everyone that we give a gift to is someone to whom we have a personal connection. But, whatever our reason is for giving the gift, the mere fact that we are willing to extend something "extra" to another is an indicator that we care for that person on some level. But what if the person that we care for and wish to give a gift to appears to have everything? How do we go about choosing the appropriate gift under these sometimes very nerve-wracking circumstances?
The first things to determine are for what purpose is the gift being given and just how much do we truly care about the person to whom we are giving the gift? If the purpose of the gift is something initially impersonal, such as being invited to a wealthy person's house for the first time who might later become a friend, then my recommendation would be to make the gift fit the occasion and not to spend too much on the gift. Consider a nicely-put together gift basket of wine and cheese or some other food assortment. Such baskets come in price ranges from the very low to the very high and are usually put together with comparable quality regardless of the amount that you have spent. Moreover, this is a practical gift that makes a good impression and will most likely be used on the spot.
If, similarly, you are invited to a commemorative event (such as a graduation) of the child of a wealthy family to whom you are barely acquainted, I would again recommend something small, occasion-appropriate, yet not too personal. Consider an attractive "Congratulations" plaque or a small wall hanging with an interesting saying. Again, these items range in price and are easily accessible at many card and novelty stores. Most of them are, in fact, very attractive and will most likely be kept and refereed to by the recipient for years to come. The important thing in these "acquaintance" gift-giving situations is to politely extend the gesture but not to go overboard or be too lavish.
If, however, the gift is meant for someone that we care deeply about that we know full well has more than we do, then most of us will likely want to make the gift much more personal. And, when we want to give a personal gift because we do care deeply for another person and that person seems to have everything imaginable, this is likely to make the gift-giver very insecure, concerned or nervous. The gift-giver's mind will reel, "What if they don't like it?" "What if it is not enough?" "What if they were expecting something better or different than what I chose to give them?" This is a definite sign that you care. And it is quite likely (in fact, even probable) that if you are that worried about the gift and the person's reaction to it that much, than BOTH of you care very deeply for each other.
The first thing to do here is to relax. Realize that if your friend (recipient) cares for you as deeply as you do them, then they are probably hoping for something personal, special, and reminiscent of you or the moment that the gift was given. If you truly want to impress this person, you can. But you shouldn't have to if your connection is strong. And, most likely, if the recipient does have everything, the last thing they need is something materialistic and the first thing they need is something that assuages their own insecurities. If you do too much to impress them materialistically, your recipient might think, "I love or like this person so much, but they are throwing something lavish at me to impress me. Do they really care about me? Or do they just think that they have to get me something extravagant?"
If you WANT to do something monumental or palatial because of a true love, a deep pride, or a goodness of heart, then do not let this person's potential fears or inner-rumblings stop you. And when you present the wonderful gift, you will of course, explain the depth from which it came. The recipient will know how much you care, believe your sincerity, and appreciate it so much.
But if you give something big because you feel that you HAVE TO impress them, then you are doing it for the wrong reasons and the relationship that the both of you so greatly value is likely off balance in some way. Once you have calmed your own doubts as the gift-giver, choose from the heart. Your gift could be as simple as a flower or as complex as a condo. But if it is heartfelt, something that you wanted to do and something that is representative of yours and the recipient's deep connection, then whatever the gift it will be cherished.