The level of difficulty in dealing with a cheapskate is directly related to how close your relationship is with him. If your husband is a cheapskate, you may need to change your outlook and approach, whereas if the cheapskate in question is an acquaintance, you can simply decline invitations at restaurants when you're not willing to pay the entire tip. When trying to cope with this often-aggravating behavior, it's important to focus on the person's positive attributes, rather than on his tightwad ways.
Avoid situations where the cheapskate will be overly conscious of the money she is spending, advises Michelle Crouch on NBCNews.com. Renting a canoe by the hour for an afternoon would be agony for such a person, so pay for an afternoon's worth of rental in advance. When you go on vacation, consider purchasing a package rather than haggling with the tightwad about every visit to a restaurant or each museum entry fee.
Suggest paying by credit card. Using credit cards tends to result in increased spending, notes cognitive scientist Art Markman in "Psychology Today." Although you don't want to encourage someone to develop a bad habit, insisting that he use a credit card while on a date might help if you notice that it prevents him from having anxiety about the size of the tip he's leaving.
Set boundaries before you go out with a person who is tight with money. Let her know that you have enough money to pay for your dinner and your half of the tip, but not hers. If she states that she doesn't have money, wait until she is willing and able to pay her share before engaging in an activity with her.
Praise the cheapskate when he takes a break from his behavior. Whether it's giving a dollar to the guy on the street corner or offering to pay for a friend's dinner at a restaurant, let him know privately that you're impressed by his generosity.
View the tightfisted person with compassion. The tendency to be too careful with money may arise from a fear that disaster could strike at any moment and the resulting need to be prepared. In this case, each dollar spent could represent a chink in the wall of protection the cheapskate has built between herself and being destitute.