90 Funny Who Knows The Retiree Best Questions (2024)

Are you thinking of how to make a retirement party for your dear one?

Well, there are so many things that need to be considered while planning a party for your dear one.

You need to think of a theme, menu, and the best way to celebrate it.

But what games are you gonna put in that retirement party? 

How about “Who knows the retiree best questions“? Yes, this is a game to know who is the closest person to the retiree and the relationship between them.

You can ask these questions to all the people invited to the party. Such as co-workers of the retiree, family members, and even friends who are working in different fields.

Who Knows The Retiree Best Questions To Play

Who Knows The Retiree Best Questions To Play

We have collected fun retirement party questions you can add to your game cards.

In order to ask the guest “How well do you know the retiree?” this is the best thing you can do.

These questions are not just for fun but will also let all know about the retiree’s personality.

Here are 90 who knows the retiree best questions for a retirement party that you can play at your next gathering.

1. What is their favorite pastime?

2. How long did they work in that company?

3. Do they still keep in touch with their previous work colleagues?

4. Do they have any hobbies? What’s their favorite hobby?

5. Who do they trust the most?

6. How many times have they visited that place?

7. What was their first job?

8. Have they ever been abroad?

9. What’s their favorite food?

10. Is he/she a morning person or a night owl?

Funny Questions For Retirement Party

11. Do they like to travel or prefer staying at home?

12. Do they have any pets? What was the name of that pet?

13. What did they think about their first love?

14. Do they have any children? How old are they?

15. Have they ever cheated on someone?

16. What’s the name of the first boy/girl they met they liked?

17. What’s their favorite movie and book? What was his/her first movie?

18. Who is their favorite actress/actress?

19. What are their favorite musical artists? Name one favorite song of him/her.


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What Describes The Retiree’s Best Questions

What Describes The Retiree's Best Questions

In this section, there will be given two options in the card and the guest will tick the right/wrong based on how well they know the retiree.

For example:

You can have two options like Mountains/Beach.

The one who knows the retiree and what option is right for him must check the option.

The one who gets all the answers right will be the winner.

Here are some options you can add to the ‘who knows the retiree best questions‘ game:

20. Mountain/Beach

21. Country/Rock/Pop/Romantic (we tried adding more than two options here.)

22. Art/Photography

23. History/Geography

24. Football/Basketball

25. Religion/Culture

26. Music/Politics

27. Science/Math

28. Rain/Sunset/Sunrise

29. Street/Townhouse

30. Sea/Lake

Retirement Trivia Question

31. Zoo/Campsite

32. Gardening/Farming

33. Coffee/Tea

34. Bar/Pub, Wine/Beer

35. Beach/Hiking

36. Vacation/Travel

37. Theatre/Concert

38. Museum/Gallery

39. Park/Golf Course

40. Vegetable/Fruit

41. Summer/Winter

Also, remember this is just an idea for you to get creative and create your list!

Who Knows The Retirees ‘First’

Who Knows The Retirees 'First'

Here you will find the ideas to ask your guests about the retiree’s first thing they had or know about.

For example:

What was the retiree’s first job?

What first car does the retiree buy? etc.

This will let the retiree know that you are interested in their story and that you care.

42. What was the retiree’s pet?

43. What was the retiree’s first vacation?

44. Who was the retiree’s first date?

45. What was the first thing the retiree bought on their own?

46. When did the retiree’s first grandchild arrive?

47. What was the first concert the retiree went to with a date?

48. What was the first gift the retiree gave to someone he/she loved?

49. When was the first time the retiree cried because of someone else?

50. When was the first time the retiree got their teeth fixed?

51. What was the reason for the first job the retiree got fired from?

Fun Questions To Ask a Retiring Employee

Remember, the goal here is to make it interesting, but at the same time, you don’t want to be too personal because the conversation will likely die if the retiree feels like he has to explain his life story to you.

Who Knows The Retirees ‘Favorite’ Things

Who Knows The Retirees 'Favorite' Things

This can be a great test for the guest and a way to know how much they know about the retiree.

Make sure that you put some thought into this and make it fun.

Here are some questions you can add to the retirement game card:

52. What is the retiree’s favorite song?

53. Do you know the retiree’s favorite holiday destination?

54. What’s the retiree’s favorite dessert?

55. What was the retiree’s favorite gift?

56. What is the retiree’s favorite sports team?

57. What’s the retiree’s favorite color?

58. Do you know the retiree’s favorite drink?

59. Where is the retiree’s favorite restaurant?

60. Is there anything the retiree won’t do or can’t do?

61. Name one movie that he loves to watch.

62. What is the retiree’s favorite ice cream flavor?

63. What are the retiree’s favorite books?

64. What is the retiree’s favorite time of day?

Well, these can be asked for fun and they are not hard to answer at all. 

The one who is close to the retiree can answer all the questions about the retiree easily.

Never Have I Ever Retirement Questions

Never Have I Ever Retirement Questions

This is one of the most entertaining games you can play with the retiree and you can ask them as many questions as you want. 

As long as it has nothing to do with your age and retirement, they will have no problem answering them.

We tried to come up with as many fun questions to ask someone retiring and have them write them down.

Here are some questions you must include at the retirement party:

Let’s never have I ever be common here. I will just add the statement.

65. Been arrested.

66. Left the country.

67. Fell off a boat.

68. Skipped any class.

69. Drank rotten milk.

70. Swam naked.

71. Watched a movie without a ticket.

72. Cheated on exams.

73. Been to a casino.

74. Punched someone.

75. Stole food from the college canteen.

76. Go shopping without your parents’ permission.

77. Went to a party just to meet girls.

78. Gone two days without showering.

79. Kissed when you shouldn’t have.

I hope you got a clear idea of what type of questions you need to add to your card.

Questions To Ask About The Retiree’s Future (Plan)

Question To Ask About The Retiree's Future

It’s actually a great part you can add to the party quiz. It’s a good way to get to know people better.

You can add more questions like: What is their plan after retirement? How much do they have saved for retirement? What do they plan to do once they retire? and so on.

Once you get to know them, you will also find out about what they enjoy doing once they retire.

For instance, if they are a retired banker, then it would be great to get to know what he or she does in their spare time.

80. Have you planned any business after retirement?

81. What are your plans for future growth?

82. Have you received any special training while working, and if so, what was it about?

83. Do you have any hobbies or anything you do when you’re not at work?

84. Who is your best friend? Is he/she still your best friend even when you retire?

85. What is the best thing that has happened to you so far in your life?

86. How would you describe your personality?

87. What’s the most difficult thing about retirement for you?

88. How much money do you make per year and have you saved any money?

89. If there were two things you couldn’t live without, what would they be?

90. If there is something you’d like to do but haven’t had the chance to do yet, would you like to start doing it now?

Questions To Ask About Retirement Pension

Understanding a retiree’s perspective on their pension can be both enlightening and amusing.

These questions can tease out stories and plans related to their financial retirement journey.

What’s the first thing you’ll purchase with your pension?

Have you named your pension fund? If so, what is it?

If your pension was an animal, what would it be?

What color do you think your pension would be?

How would you celebrate your pension’s birthday?

If your pension could talk, what would it say to you?

What’s the most outrageous thing you’d do with your pension?

If your pension was a movie genre, what would it be?

What superhero power does your pension have?

How does your pension inspire your retirement dreams?

If your pension was a cocktail, what would be in it?

What’s the theme song for your pension?

If you could go on a date with your pension, where would you go?

What’s the pension’s favorite holiday destination?

How would your pension dress for a costume party?

Questions To Ask About Retirement Pension

How Well Do You Know Your Coworker

A retiree’s coworkers often become like a second family.

These questions are designed to see how well they know each other.

What’s that one work story about the retiree that everyone should know?

If the retiree had a work superpower, what was it?

What’s the retiree’s go-to ‘work snack’?

Which coworker knows the retiree’s coffee order by heart?

What’s the retiree’s most memorable office prank?

If the retiree’s career had a mascot, what would it be?

What’s the retiree’s signature ‘work phrase’?

Who’s the retiree’s work best friend?

What’s the retiree’s most legendary work achievement?

How did the retiree make the workplace better?

Retirement Questions For Couples

Retirement for couples is a new chapter filled with shared experiences.

These questions explore how couples envision and plan their retirement life together.

Who’s more likely to forget where the retirement fund is kept?

If your retirement was a tandem bike ride, who would pedal more?

What’s the first rule in your retirement ‘couple’s handbook’?

Which of you is more likely to splurge the retirement savings?

Who’s in charge of the retirement adventure map?

What’s your dream retirement home, and where is it?

Who’s more likely to take up a quirky new hobby in retirement?

If you could retire anywhere in a book or movie, where would it be?

What’s the most romantic retirement getaway you’ve planned?

How do you plan to spoil each other in retirement?

Retirement Questions For Couples

Retirement Jeopardy Questions

Mixing knowledge with nostalgia, these jeopardy-style questions are perfect for a retirement party game show.

What year did the retiree first join the company?

Name the retiree’s all-time favorite work project.

What’s the retiree’s record for most cups of coffee in a day?

Identify the retiree’s most used software at work.

What’s the title of the retiree’s favorite industry book?

Who was the retiree’s mentor when they started?

What’s the biggest change the retiree witnessed in the company?

Name the retiree’s most frequented lunch spot near work.

What’s the retiree’s usual sign-off in emails?

Guess the retiree’s ‘hidden talent’ that the office knows about.


Who Knows The Retiree Best Questions - Conclusion

In conclusion, these are the questions that will add fun to the party and make your guest’s trip a truly memorable experience.

You don’t have to be limited to only these questions, you can ask your guests more questions that come to your mind and get to know them more.

This question game will surely let you know who knows the retiree best.

Also, let us know what games you play at the retirement party and what are your favorite questions. Please comment below!


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Your friendly neighborhood. I do SEO (Freelance Content Writer), and sometimes I cook food.

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