I hate criticizing other women’s parenting choices, but every once in a while there is someone who will bring out the judgmental side in me. Paging Lori Drew…

Most recently I was shaking my head at this letter to financial expert Suze Orman in Oprah magazine:

I AM A 59-YEAR-OLD widow. My husband left me and the children in good shape financially. I’m trying to help my daughter through graduate school, but the real problem is my 41-year-old stepson, who is always asking me for money. Since he got married and had a baby, he’s even worse off. I’ve already given him a spare car; the other day he asked to borrow $200 from my daughter. I’ve stopped answering the phone because it’s so hard for me to refuse him. At this stage of my life, it would be nice to do some redecorating around the house and maybe even get plastic surgery, but I feel so guilty that my stepson doesn’t have enough to get by. Should I keep helping him?

Let me get this straight. She would rather get plastic surgery than help out her grandchild? What kind of priorities are those?

But she did touch on an interesting question I want to pose to you, MotherTalkers: Do you consider graduate school a necessity that should be covered by mom and dad? I emphasize education in our home -- and I do think a college education is necessary in today’s economy -- but I always assumed DH and I would help pay for the children’s undergraduate education and they would be on their own in graduate school.

I do not have a graduate education. My husband took out student loans to pay for law school. So I am surprised this mom saw nothing wrong with helping her daughter, yet is grumpy about helping the stepson with a new baby.

Orman answered thoughtfully in that she questioned how the son spends his money. Is he irresponsible with money? Does he not work? I would be resentful to help out, too, if this were the case.

She also reminded the mother that she was entrusted with her husband’s money and that allocating it to a well-meaning child in need trumped her own desires for plastic surgery and redecorating her home. (Amen!)

Note: This is an ongoing series about my 22-year-old “baby” sister who has lived with us for 3.5 years. -Elisa

It’s official. My 22-year-old sister moved to her own apartment this past weekend after 3.5 years living with us. We may have given her a little nudge, but we parted on good terms.

We let her keep her bedroom furniture and told her she can always count on our help when she needs it. We plan to turn her room into an office -- actually we shamefully went to Ikea the same day she moved! -- but there is a guest room for when she needs it.

We were at a friend’s house by the time she left so there were no tearful good-byes or any drama at all. I found a note in the kitchen with her new address and a big “Love you!”

I’ve been holding back from calling her, wanting her to settle into her new place. Despite my worries, she’s been quite resourceful: She got her friends to move the furniture, saving her moving costs. She found a room in Oakland for $400 a month, which I did not think possible. And she was accepted to San Francisco State University, which she will start in the spring. This young woman is much more capable and resourceful than I gave her credit. I just did not allow her to show it.

Of course, I don’t think having an adult sibling in the home is the same as dealing with your own children as the expectations and obligations are different. But I do feel like a proud mother.

I was eight-years-old when my sister was born. I remember her birth, changing her diapers and even teaching her how to walk. I will never forget her first steps. We were on our porch in our childhood home in Miami, I propped her on her feet and continuously told her, Parate! Parate! Stand up! Stand up!

She did, with a huge grin on her face, take two steps. I called my mother. But when my mom arrived at the scene, my sister stumbled, fell on her bottom, no one to witness her first steps except for me.

Now I get to see this competent young woman take this major step in her life and I am filled with contradictory feelings: pride, fear, ambivalence, relief. I wonder if this is how I will feel when Ari heads for college?

Unfortunately, my long weekend was off to a rocky start. There were fireworks at my house as my husband confronted my 22-year-old sister and told her to find a place of her own.  

As you may recall, my baby sister (she is the youngest of four children and I am the oldest of the four) came to live with us 3.5 years ago. She was estranged from my parents in New Hampshire so she came to live with us in California and attended the local community college. She was 19.

While we never established any ground rules, we assumed that she would help with her newborn nephew in exchange for free room and board. It never happened. Well, at least not consistently.

Initially, she was grateful to have stable housing so she was very helpful. She was so helpful that my husband and I began to pitch in $500 a month for her to have spending money. But then school started, she made friends and disappeared. She told us not to worry about paying her and instead found a higher paying job. The problem is she was living with us rent-free and wasn’t contributing anything for it. We grew resentful as she used our home as a crash pad and for free food and laundry. Even more insulting, some of her friends at the community college had children! Yet, she acted like hanging around us was a burden to shoulder.

I approached her a couple times about pitching in, which the first time she acted flabbergasted and threatened to find another place to live. That was six months ago. The second time she was more gracious and offered to draw up a schedule to earn her keep. The arrangement lasted two weeks. We went to Europe, came back and found out she took a job, which would take her even more time outside the home.

“I will try to fit you in,” she told us sheepishly. Try? In the meantime, Markos and I were passive-aggressive as we always were with my sister. I wanted so badly to support her until I felt confident she could stand on her own two feet. Because she was my sister, my husband was always reluctant to say anything to her.

But after weeks of stewing, all the pent up resentment boiled over. He was upset she did not help me the week he was on the east coast for the Colbert Report. She knew I was home alone with the two kids.

On Saturday morning my husband confronted her. “I am concerned that we made a deal and you have not been helping out like you said you would.”

When it comes to adult children, where exactly is the line between helping and enabling? When is it time to tell them they need to move?

These questions weighed heavily on my mind as I reached a crossroads with my 22-year-old sister, who has lived with us for 3.5 years and counting.

Until now -- I will get to that in a minute -- she has used our home as a crashing pad for free room, board and laundry services. Our cleaning lady even cleans her room! And while she will help out with the kids when I ask her, she will never offer and has done little in the way of household chores. Our friends are surprised Markos and I rarely go out, considering we have another adult who lives with us rent-free a half a block from public transit in one of the priciest cities in the country.

But I have only myself to blame.

When my sister came to live with us, she was a 19-year-old who had been living in the smoky basement of her then boyfriend’s parents’ house in New Hampshire. She was estranged from my parents and unsure of her future.

We had a new baby and I was feeling overwhelmed taking care of him by myself while DH traveled to D.C. on business. In what we considered a mutually beneficial relationship, Markos and I invited her to live with us and we assumed she would help out with Ari. Looking back on it and as crass as it sounds, we should have drawn up a contract laying out what she would have to do to earn her keep.  

But we didn’t do that and, instead, I often found myself feeling resentful like her mother more than her sister. About a year ago, I spoke to her about helping out and she did -- sulking -- by occasionally washing the dishes until my mother recently came and took over the task. Both my mother and mother-in-law -- who noticed my sister’s frequent absenteeism and messy room -- have left.

Our home technically has three bedrooms, and we are using an additional "den" as Ari's room. We still need an office, and eventually will need the two upstairs rooms -- including my sister's room -- for the kids. Markos and I came to a tough decision: It was time to hold The Conversation with my sister as to her future plans. It was time for her to grow wings and fly away from home to financial independence.