A cheapskate is a negative term for a person who saves money and resources. While there are plenty of positive terms in the English language for a person who saves money, the use of the term cheapskate is intended to characterize the frugal person as someone who hoards resources at the expense of others. As such, it is frequently used as a direct insult, or during a recounting of precisely how, in a particular instance, the person was a cheapskate.
The origin of this word is heavily debated, but it is often thought that "skate" is a derivative of a word meaning "creep" or "guy," with "cheap" retaining its current meaning. Other folk etymologies revolve around a "Cheap's Gate" where miserly people once hung out, a skate worn on the foot, or even the fish "skate." These are each frequently championed, but there is no clear etymology of the word.
Being a cheapskate is not the same as being poor. A cheapskate has money and refuses to spend it. In the past, people who were poor and unable to spend money were characterized under this moniker, but more recently sensitivities to poverty have made it socially acceptable for poor people to devote themselves to self preservation.
Many people do not view saving money as a negative quality. In fact, being thrifty or frugal is almost always a positive trait, and having a large savings account can be considered a positive attribute. Even so, the same people who view saving money in a positive manner may also observe certain situations in which being polite or gracious involves spending money. It is a disregard for these situations that differentiates a positively viewed frugal person from a negatively viewed cheapskate.
It is almost always expected that if someone attends a function where gifts are customary, he or she must bring a gift that befits one's personal wealth or the occasion. For instance, a child may give a handmade card as a birthday gift, but a middle class adult may be expected to bring a gift that is within a somewhat flexible appropriate monetary range. These guidelines are rough, but vast deviance from them with the intention of saving money is a characteristic of a cheapskate.
Other causes that require monetary expenditure include sharing a meal, drinking in a bar, or going on a date. Human charity is also sometimes considered a situation that demands monetary contribution, but this is typically only true if someone agrees with the cause and has sufficient funds. Even within communities that use the term cheapskate, the situations where money must be expended in order to not be characterized as miserly may be somewhat different. Most people intuitively recognize what these situations are for cultures with which they are familiar, and therefore avoid acting in ways that would qualify them as miserly.