At first, it didn't seem like a big deal. Your friend needed a couple bucks here and there which you lent them, you paid for a couple of the pizzas "you both ordered," you did all the carpool driving because their car was "in the shop." Now it's a year later, and those few couple of times have turned into you feeling used, abused, and taken advantage of because your friend or family member has yet to shell out a single penny to help pay for anything or worse, pay you back for the many Many MANY loans they've taken out of the bank of you. Now that you are thoroughly pissed off, what can you do?
1. Do not apologize
Remember how you've been going to work to earn money to pay for stuff you want and need or to provide for your family? Yeah, you! You do not need to apologize for not being able to loan a moocher more money, or not wanting to go out to eat because you don't have or want to spend cash for both of you to eat. It's your friggin' money, and you may damn well do with it what you please and if that means you spend it on you and your family, then so be it. You owe the freeloader nothing. And NO it does not matter if you are what someone else would consider rich. It is not your sole responsibility to make sure that everyone around you is taken care of just because they put out a hand and you have money. It's not to say never loan, never help, spit on people who get in your way...but it is to say, that moocher thinks that because you have money, you are responsible for supporting them, and you're absolutely not.
2. Confront them
A lot of people don't have the nerve to do this, which enables the moocher and then you allow them to keep mooching. Pull them aside one day and talk to them. "Hey man, I've been paying your car payment for 3 months now and you haven't paid me back, so there will be no more loans until you've paid me back for the loans you already owe me. If you can't or won't do that, then don't expect to come to me in the future because I lent you money in good faith, and you're not being a good friend or family member by not paying me back because now I'm losing money which isn't fair to me at all."
3. Get it in official writing
A lot of people loan money to moochers on good faith or on a friendly handshake, but a moocher does not respect this, so if they want something from you, make it legal. They must sign an actual legal contract in front of a witness if they want money from you in case later on down the road, you need to take them to court for bigger loans that can and will hurt you financially if not paid back.
4. Get the money upfront
Moochers get into the routine of just assuming they can con or mooch some money off of someone else in your family/friend group. So if others are also aware of this persons behavior, let everyone make it crystal clear, if you are all for example, going on the vacation, payment in full for xyz must be made up front before the trip begins. Or when you get in the car, literally ask to see this moochers wallet and confirm there is money inside because they seem to always forget their wallet or to bring money.
5. Distance yourself
Harder if you are family, but with friends, you can still be a friend to someone without being their personal bank. Hang out when you do free stuff or stuff you know they have already paid to do, or only offer to do free stuff with them so there is no need for money talk. If they inquire as to why they aren't getting invited to more stuff, you can talk to them about it if you haven't already, but again, you owe them no apologies. Mooching isn't a one time thing, it's routine, and if you're at this point, it is long past routine.
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Goodtake. I would add
6. Moouchers have a history so don't lend anything to someone with a habit of screwing over those that have helped them.
Been there and never got any money back