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[quote=Anonymous][quote=Anonymous][quote=Anonymous][quote=Anonymous]I'm in my late 30s, single (dating in search of a long-term partner), and living in a medium cost of living city. I'm a first-generation grad and finally got a decent paying job (double the starting salary of my current role). My family and friends have been nothing but supportive of my career, as I've had a lot of setbacks (chronic medical issues and job loss twice in 3 years). I'm finally happy to get back on track, but unfortunately, I have debt (student loans, credit cards, etc.). I will be comfortable, but I plan on saving and paying down as much debt as possible. My oldest sibling is a single parent of 3, and the dad is not in the picture. She expects me to give her a "financial gift." Last year, I did tell her that I would pay for her oldest's SAT or ACT prep course. That's it. Also, my mom gifted me a laptop this year and said that it was my birthday and Christmas gift (which I'm 100% okay with). She let me know that she wants her money back. I explained to her that the laptop was a gift and typically gifts are not paid back. She makes more than I do currently but less than what I will make in my new role. I definitely do not want to be stingy or selfish, but I am not in a place to reach my financial goals and give money to people.

I want to put my foot down now and set the expectations and boundaries that I will not and cannot be their support system. Suggestions?[/quote]

Gift your mom the laptop money + a small gift back.  Call it what it is - return of the laptop money, Christmas gift, birthday gift.  Let her know that going forward you only will participate in a family Secret Santa with fixed price point.

Give what you promised your sister...but not more.

Also, looking at your family's financial situation, you may start putting away a small sum of money for your sister and mother each month, so if you are asked to give for a specific dire emergency  you can do so. Don't tell them about this.

Live like a starving artist and pay off your debts. This means that you live with room-mates, cook all your meals yourself and buy work clothes from thrift stores.

Let them know that you are trying to dig yourself out of debt.

[/quote]
Hilarious that you are telling op to live like she's a starving artist but you expect her to save money for her sister and mother both who seem unreasonably entitled to the money she is making from her new job.

She's lost her job 2ce in 3 years. In this environment, it will happen again. No one has job security and she should be living like she's poor to deal with that, not to save money for fully functional adults who made life choices that made sure they stay poor.

Your mother didn't give you a birthday or Christmas gift. Do not give her gifts for either. Doing what she did is despicable. You don't asked to be paid for gifts. Awful.

Never talk money with them.

No more financial gifts for sister. You need to back up quickly when someone assumes they have dibs on your money.

You save money for yourself. Do not set up a fund for your family. That's insane.  Go read about the crab pot mentality of poverty. [/quote]

What you are suggesting is that OP cuts all ties with her family. Right?  Is that what she wants?  She is a single woman who has come from a not affluent family with dysfunction. Her own family has supported her through joblessness etc, and she has reached where she has reached through their support.  If OP does not want to cut all ties with her family, then she needs to have some money set aside for dire situations when her family needs her help.  My idea to have a secret fund in case her family asks her for money in dire situations is a good one.  OP is not an orphan.  She is a normal human being who does not hate her family.

She does need to return the money (or just the laptop) to her mom.  Even if her mom makes more money than OP, the gift giving goes both ways.  (Most probably mom will give OP's returned money  to her daughter who has 3 kids.) 
If OP wants to stop giving financial gifts to her family, then she needs to return the money /gifts they may have spent on her.  Yes, it was a gift...but OP comes from a family that is expecting her to give financial gifts to them.  She needs to return their gifts and only then can she stop giving money to them.

After that, she needs to live a life of frugality for some years so that she is free of all debt.  OP needs to take some online lessons on how to do that, because her family training and culture is not conducive to financial freedom and prosperity.

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