AITA for telling my grandma to pull herself up from her bootstraps?

In a sprawling family home filled with echoes of wealth, a grandmother’s sharp tongue cuts through a quiet dinner. Known for her lavish lifestyle and blunt opinions, she scolds a guest for their family’s poverty, preaching the gospel of “pulling yourself up by your bootstraps.” The room squirms, but her words linger like an unwelcome guest.

Fast forward, and Grandma’s own financial troubles surface, her summer home unsold and savings dwindling. When she laments her woes, her grandkid flips her advice back at her, sparking a family firestorm. Was it a clever clapback or a cruel jab? Reddit’s buzzing with takes, pulling readers into a drama as juicy as a soap opera.

‘AITA for telling my grandma to pull herself up from her bootstraps?’

My grandparents were extremely rich. They sent their 3 kids to expensive boarding schools growing up and paid for all their schooling. They had a huge house and lived very lavishly. They eventually retired and bought another very expensive house in a different state to go for the summer.

My grandfather passed a little while ago and he had dementia. He was in charge of all my grandparent's finances even when he had dementia. My grandma never saw a problem with this. Now my grandmother isn't doing that well financially.

She's trying to sell her summer home and it's really not working and she also got messed up financially from her husband taking care of everything. Its just pretty much a mess but she still has her house where we live most of the time and enough money to live.

My grandmother has always told our family how lazy poor people are and if they simply worked harder, they'd be fine. It was really awkward when my brother's girlfriend came over and my grandma kind of berated her for being poor.

My dad asked my brother's gf how her family was doing and she just answered its a bit hard financially and that her mom's hours were getting cut. She lives with a single mom who works 3 jobs and barely makes 30k a year. My grandma basically just told her mom should just work harder and pull herself up from her bootstraps if she wanted to stop making 30k.

My brother's gf just kind of said how the 3 jobs is already a lot of work and physcially demanding for her and stuff and my grandma just yelled at her for making excuses... and went on to say how privileged she is for going to college for free because she's poor and stuff like that. It was really difficult to watch.

My grandmother recently was lamenting over her financial troubles and was saying how terrible everything is for her and I told her to just 'pull herself up from her bootstraps.' She got really mad at me and said how dare I make fun of her during her weakest time in her life.

My mom defended her saying that what I said was cruel to kick her while she's already down. She wants me to formulate an apology to her in written form by tonight but I honestly don't think what I said was that bad.

Family dinners shouldn’t double as battlegrounds for class warfare. This grandkid’s sharp retort to their grandmother exposes a clash of privilege and perspective. Dr. Derald Wing Sue, an expert on cultural dynamics, notes, “Unexamined privilege can lead to insensitive judgments about others’ struggles”. His insight frames Grandma’s harsh words and the grandkid’s comeback.

ADVERTISEMENT

Grandma’s “bootstrap” mantra dismissed the girlfriend’s family’s hard work, ignoring systemic barriers. A 2023 study shows 60% of low-income workers face job instability, like hour cuts, limiting upward mobility. Her later complaints about her own finances—despite owning two homes—felt hypocritical to the grandkid, prompting the jab. Both have valid emotions: Grandma’s stress, the grandkid’s frustration.

Dr. Sue suggests empathy can bridge divides. The grandkid could’ve explained how Grandma’s words hurt, fostering dialogue. Grandma might reflect on her privilege.

Check out how the community responded:

Reddit served up a feast of opinions, with a side of wit to lighten the mood. Here’s what the community dished out:

ADVERTISEMENT

butt5000 − NTA your grandma deserved to be called out for being s**tty. She’s lived a life of privilege and clearly hasn’t considered how other people may not benefit from the same privileges she has.

orngckn42 − NTA, 'Grandma, I'm sorry you did not like your own advice, I just figured since you were down on your luck right now you could use a reminder of how easy it is to get back on top! You always lamented how money problems could be solved if people weren't so lazy, and as you've never had these money problems before, I know you're not lazy!

I was simply trying to help. Love, your darling OP'. Edit: thank you u/basketma12 for my first ever Reddit award!. Edit 2: my highest-rated post is a polite 's**ew you' letter to grandma... lol, thanks for the karma guys!

ADVERTISEMENT

Mirianda666 − NTA. I know a lot of people will disagree with me about this because 'respect to elders' blah-blah, but I don't see how it can be disrespectful to repeat the words that person has spoken right back to them. Shows that you were listening to them and paying attention to what they were saying. 'I'm sorry I hurt your feelings by repeating the words you said to brother's girlfriend.'

GoGoGorbachev − Now my grandmother isn't doing that well financially.. What?. She owns a summer home and has 'enough money to live.'. She's doing fine.

[Reddit User] − NTA don't apologize. How old are you for your mother to tell you to write an apology?

ADVERTISEMENT

thelasttimelord12 − NTA “Dear Grandma, sorry you haven’t pulled yourself up by the bootstraps yet. Probably should get started on that.. Sincerely, OP”

conditionalinterest − NTA. 'Dear Grandma, I'm sorry you felt my reiteration of your advice to those experiencing financial strain was mocking. Given your earlier vehement speech towards [brother]'s girlfriend, it felt appropriate to reaffirm your beliefs. Values make the person as we all know. Maybe you'll find a buyer within the next two years if you spent less time making excuses.'. [OP]

ZeeLadyMusketeer − Nta. Offer to apologise to your grandmother once she has proffered one to your brother's gf. Your apology will match hers in sincerity and tone.

ADVERTISEMENT

BlairIsTired − NTA. Act like trash, get treated like trash

KeimeiWins − NTA Most people just find it easier to let Nana be rude as f**k until she dies, good on you for pointing out her s**tty attitude.

These Reddit takes are spicy, but do they untangle the family knot, or just fan the flames?

ADVERTISEMENT

This grandkid’s bootstrap quip stirred a family pot already simmering with tension. It’s a reminder: words carry weight, especially when privilege blinds us. Was the comeback a teachable moment or a step too far? Have you ever called out a family member’s hypocrisy? What happened? Drop your stories below—let’s unpack this family saga together!

Share this post

Related Posts

Leave a Reply

Your email address will not be published. Required fields are marked *