10 Questions Retirees Wish You Would Stop Asking

Retirement shouldn’t be a time of having to answer intrusive questions.

stressed senior woman
Updated July 18, 2024
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Retirement is sometimes seen as an endless stretch of carefree fun where you revel in mall-walking, enthusiastically look after the grandkids, and try to make the 4:30 p.m. early-bird special.

Yes, people have lots of assumptions about what a stress-free retirement is like — and retirees wish you would stop making them.

Perhaps more than anything, retirees hate the following common questions.

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‘How large is your nest egg?’

Prostock-studio/Adobe mature man squinting using laptop

This question — along with “How much money do you have left?” — is one of the most offensive queries retirees get. It’s an invasion of privacy that puts someone on the spot.

Also, it assumes the retiree has a nest egg. In truth, many folks are barely scraping by on Social Security and little else. And no, they don’t want to talk about it.

‘What do you do all day?’

pikselstock/Adobe elderly man using laptop

This is another much-loathed question, as it implies retirees no longer have obligations. In an underhanded way, it suggests sloth.

Many retirees have activities that keep them plenty busy. But really, it’s none of your business.

A better question might be to ask them about their interests and hobbies in the same way you would ask a person who isn’t retired. Ask about the person, not about their supposedly empty days.

‘Why aren't you working?’

Prostock-studio/Adobe mature woman rubbing her eyes

Let’s be honest: This question is dumb. The reason retirees are not working is because they are retired.

Perhaps they stopped working as a well-earned reward after decades of work. Or it could be health issues and family responsibilities that forced them to cut short their working years. Either way, respect their privacy.

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‘Don’t you get bored?’

Raushan_films/Adobe tired tense female sitting alone

Retirees get this question all the time, especially from career-centric folks who can’t imagine not working anymore.

Many retirees have no time to get bored. They are too busy enjoying life. With work behind them, they now find the freedom to pursue interests, hobbies, and travel, or to enjoy life at a slower pace not dictated by the employer’s time clock.

Assuming they must be bored shows a lack of understanding of how rich and fulfilling retirement can be.

‘Can you help me with (fill in the blank)?’

Watercolor_Concept/Adobe senior man sitting alone

This question comes loaded with a sense of entitlement — on the questioner’s behalf — and annoying assumptions.

While many retirees enjoy helping friends and family when they have free time, they have limited free time just like anyone else.

Not only does the question assume retirees have nothing but time on their hands, but it implies that any deliberate “withholding” of assistance is selfish and rude.

‘Are you volunteering or doing something useful?’

Prostock-studio/Adobe woman talking on mobile phone

Another rude zinger, this question implies retirees need to do something useful with their time.

Volunteering can be a fulfilling activity at any age. But like anyone, retirees are free to spend their time as they see fit. If that means contributing time to a worthy cause, great. But they have earned the right to do as they please.

‘Don’t you worry about running out of money?’

fizkes/Adobe worrying woman listening to daughter

Retirees have enough financial anxiety without you adding to it. And unless a retiree has told you they are running low on money or are worried about it, it’s none of your business.

Granted, the situation is a bit different if you are asking your elderly parents whether they are doing OK financially. That can be a loving gesture, and may be necessary if you are in a caretaker role.

But the phrasing, “Don’t you worry about…” is neither tactful nor polite, and can make the interrogated retiree feel judged.

‘Do you sleep in late every day?’

PinkBlue/Adobe man lying awake in bed

This question presumes retirees are lazy and have no obligations or responsibilities requiring them to get out of bed.

On the contrary, many retirees maintain structured routines and are very active. They probably wish they had the time to lounge around in bed on some mornings.

‘Don’t you miss your old job?’

K Abrahams/peopleimages.com/Adobe sad elderly person with depression

Before you ask this question of a retiree, let’s turn it around: How many of your old jobs do you miss?

While retirees might miss certain aspects of their work life, most are perfectly content to leave those years behind.

Also, don’t forget the possibility that this could be a sensitive subject. Maybe the retiree was forced out of a job due to their age or health issues and didn’t leave their last job willingly.

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‘When are you going back to work?’

Azeemud/peopleimages.com/Adobe mental health and brain fog

This question is personal and loaded with judgment. Many retirees do go back to work, driven by the need to eliminate some money stress, banish loneliness, or both.

But assuming they will return to work — and that it’s only a matter of when — is rude. It questions the life choices they have made for themselves.

Bottom line

digitalskillet1/Adobe talking sitting on a sofa

Retirement isn’t a period when you have nothing to do all day and endless time to do for others.

And just like it’s intrusive to ask people when they are getting married, having kids, or getting weight-loss surgery, it can be off-putting to question retirees about their life choices.

Someday soon, you will be planning for retirement yourself. Odds are good you won’t enjoy answering dumb and intrusive questions any more than today’s retirees do.

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Stacy Garrels

Stacy enjoys writing about fintech, consumer deals, the side hustle economy, and random tomfoolery. She's personally tried more than 100 different gigs, including being an Uber driver for one afternoon.