Whether you’re planning an outing, a group trip or going in on a gift for someone, make sure to include this person from the beginning. If they are a part of the planning, they’ll be able to tell you what their budget is and what they are able to contribute.  For example, let your cheap sibling be the first to know if you’re thinking of doing a group gift for your parents. If they want a less expensive option, they are able to suggest ideas themselves. If you had an expensive gift in mind that you’re set on, realize it may be a priority to you, but not to the other people involved.  Understand that they may not be willing to contribute as much financially to the gift, but allow them to put in what they can and help in other ways (like organization and communication). Understanding lessens feelings of resentment for everyone involved. Sometimes, people are unaware that they are doing something wrong. Maybe they assumed an invitation out meant an offer to pay as well. Make sure when you plan to hang out with this person that you set clear expectations from the beginning.  If you're eating out together, ask your server for separate checks at the beginning of the meal. If you're going out as a group, let everyone know in advance that the bill will be split equally per person. If you're hosting a "bring your own [fill in the blank]" party, let the person know everyone is expected to bring something. If they’re prepared upfront, they don’t have an excuse for cheap behavior. If expectations have been set, and the behavior continues, you may have to confront the problem directly. If the cheap person you’re dealing with is a good friend or family member, avoiding them isn't an option. It’s not about what you’re doing, but who you’re doing it with. Plan low or no-cost activities with your cheap friend.  Take a hike or some other physical activity. Watch a movie at home. Go to a park. Cook together. Look up free things to do near your city. If you want to do something with this person that you don’t think they'll be willing to pay for, consider giving it to them as a gift. This gives you the opportunity to enjoy time with your loved one without money becoming an issue.  Let’s say you’ve always wanted to take a trip with this person, but you know they won’t include it in their budget. Treat them to a short getaway for their birthday. This takes the pressure of money off of both of you. It is important that you don’t expect an equivalent gift in return. Your friend can give you a thoughtful gift without spending the same amount of money. Don’t let yourself get too hung up on price tags. If the cheap person is a colleague or an acquaintance, your best option may be to avoid going out with them altogether. You’ll be a more pleasant co-worker if you’re not carrying resentment.  Suggest bringing your lunches from home and eat together in the breakroom. Tell them you need to save money, and aren't able to go out.
Include this person in the planning. Be understanding. Set expectations. Seek out affordable or free things to do. Be a generous gifter. Avoid going out with this person.