Family
Dear Toolsie,
my parents want me to do sports i hate just for college apps, how do i tell them no
Toolsie wrote back.
Family
Dear Toolsie,
everyone in my friend group is getting phones/insta and my mom won't let me get one yet, how do i deal
Toolsie wrote back.
Family
Dear Toolsie,
My husband and I disagree about whether to send our son to private school. We can technically afford it but it would eat our savings.
Toolsie wrote back.
Family
Dear Toolsie,
My sister and I inherited our mother's house jointly and we disagree on whether to sell it or keep it in the family.
Toolsie wrote back.
Family
Dear Toolsie,
My teenage daughter wants a tattoo for her 18th birthday and asked me to go with her. Part of me wants to say no but she's an adult in three months.
Toolsie wrote back.
Family
Dear Toolsie,
My in-laws visit every Sunday without asking and I don't know how to set a boundary without causing a family rift.
Toolsie wrote back.
Family
Dear Toolsie,
My husband passed two years ago and my son keeps suggesting I move into assisted living. I don't feel ready.
Toolsie wrote back.
Family
Dear Toolsie,
My daughter and I haven't spoken in three years and I don't know if reaching out now would help or make things worse.
Toolsie wrote back.
Family
Dear Toolsie,
My father has dementia and my 7-year-old keeps asking why grandpa doesn't remember her name. I don't know how to explain it.
Toolsie wrote back.
Family
Dear Toolsie,
my daughter wants to quit soccer halfway through the season and i don't know if i should make her finish or let her stop
Toolsie wrote back.
Family
Dear Toolsie,
My mother-in-law keeps giving my kids sugary snacks after I've asked her not to and I don't want to start a conflict.
Toolsie wrote back.
Family
Dear Toolsie,
My ex is threatening to take our kid across state lines without my permission, what legal papers do I need right now?
Toolsie wrote back.
Family
Dear Toolsie,
MY BROTHER BORROWED FIVE THOUSAND DOLLARS FROM ME TWO YEARS AGO AND HAS NEVER PAID ME BACK A SINGLE CENT AND NOW HE JUST BOUGHT A NEW TRUCK AND I AM SO ANGRY I CAN BARELY THINK STRAIGHT WHAT DO I DO
Toolsie wrote back.
Family
Dear Toolsie,
My sister wants me to give her $12,000 toward her wedding and I don't think I can afford it without draining my savings, how do I say no without ruining the relationship?
Toolsie wrote back.
Family
Dear Toolsie,
My whole family votes for the opposite party from me and every holiday turns into a screaming match about politics, how do I get them to see that I'm right?
Toolsie wrote back.
Family
Dear Toolsie,
I know you're going to say it's my decision but I'm asking you directly, if you were me would you take the higher-paying job in a new city or stay near my aging parents, just tell me what you would actually do.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my teenager wants to dye her hair a bright color for a school event and my husband is dead set against it, but I don't really see the harm.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my mother-in-law shows up unannounced almost every weekend and lets herself in with the spare key we gave her for emergencies.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my 10-year-old asked why his dad and I don't sleep in the same room anymore, and I panicked and changed the subject.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my son wants to skip college and become a full-time streamer, and I don't know if I should support the dream or push back hard.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my daughter's friend group excluded her from a birthday party and now she doesn't want to go to school, and I don't know how much to intervene.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my brother and I were raised the same way but somehow he turned out to believe our parents did nothing wrong, and every family gathering turns into an argument about it.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my toddler only wants his dad to put him to bed lately and it's hurting my feelings more than I expected it to.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my in-laws keep giving my kids gifts that go against rules we've set as parents, like candy before dinner or screen time we've limited.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, I found out my teenage daughter has been talking to someone significantly older online, and I don't know whether to confront her directly or handle it more quietly first.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my sister-in-law comments on my kids' weight at every family event and calls it 'just concerned,' and I'm tired of biting my tongue.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my daughter's teacher keeps giving her extra homework as 'punishment' for talking in class, and I don't think that's an appropriate consequence.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my son got caught cheating on a test and swears it was the first time, but I found evidence on his phone that it's happened before.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my daughter wants to major in something with no obvious career path and my husband keeps pushing her toward something 'more practical.'
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, I'm a teacher and a parent keeps emailing me at 10pm demanding immediate responses about their child's grades.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my kid's school wants to hold him back a grade and part of me agrees, but I'm terrified of how it'll affect his confidence.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my son's best friend is clearly a bad influence on his grades and behavior, but forcing them apart feels like it could backfire.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, I've been secretly doing a chunk of my daughter's science fair project because I was worried she'd fall behind, and now I feel like a fraud watching her get praised for it.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my dad insists on still driving even though he's gotten two fender-benders this year, and every conversation about it turns into a fight.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my mother keeps giving away expensive belongings to people outside the family, and I don't know if it's generosity or something I should be worried about.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my parents refuse to consider assisted living even though the house is clearly becoming too much for them, and I'm the one quietly picking up the slack.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my elderly aunt just remarried someone she met a few months ago online, and the whole family thinks it's a scam except her.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my siblings live far away and I'm the only one nearby handling our aging parents' doctor appointments, and I'm starting to resent them for it.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my dad passed six months ago and my mom still sets his place at the table every night, and I don't know if I should gently say something.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my grandmother wants to leave the family house to me specifically, and I know it's going to cause serious tension with my cousins when she's gone.
Toolsie wrote back.
Family
Dear Toolsie,
I'm the first in my family to go to college and I want to switch my major from pre-med to something my parents will see as 'wasting the opportunity.'
Toolsie wrote back.
Family
Dear Toolsie,
My daughter wants me to move into an assisted living community 'while I still have choices,' but I don't feel ready, and I don't know if my resistance is denial or just knowing myself.
Toolsie wrote back.
Family
Dear Toolsie,
I have three adult children and I'm rewriting my will. One of them has been financially irresponsible for decades and I'm considering leaving him less than his siblings. I don't know if that's fair parenting or just punishing him one more time.
Toolsie wrote back.
Family
Dear Toolsie,
My adult son moved back home during his divorce two years ago and never left, and I don't know anymore whether keeping him comfortable is support or enabling.
Toolsie wrote back.
Family
Dear Toolsie,
Dear Toolsie, my 8-year-old has started narrating our family dinners like a nature documentary — 'and here, the father returns to his natural habitat, the recliner, completely unaware he is being watched' — and now I can't eat a meal without hearing David Attenborough in my head.
Toolsie wrote back.
Done here? Read a letter at random