Workdays can sometimes come with a variety of emotions ranging from frustration, stress, boredom, overwhelmed, confusion, exhaustion, and disappointment, to satisfaction, anticipation, relief, excitement, gratitude, and even creativity.
A funny, light-headed conversation always has a way of lightening the mood and creating a more enjoyable atmosphere both for you and the person you are engaging with.
For me, I use one of these twenty-five(25) creative and humorous approaches to break the ice, generate laughter, and help them loosen up.
25 Funny Ways to Ask Someone About Their Workday
- How was your day? Hope it was more like a stroll through a quiet park.
- How did your day at the office feel, like a circus or more like a relaxing day at the beach?
- You look beat. Did your workday involve any daring acts of heroism?
- How many times did you have to resist the urge to crawl under your desk and take a nap today?
- On a scale of “I need a vacation ASAP” to “I can’t wait to resume work tomorrow”, how would you rate your workday?
- How was your presentation? Did you have a “now you know who’s the boss” moment or a “let the ground open and swallow me” moment?
- How was your workday? Did you get to talk with your boss about your concerns? Should I start ironing my legal attire and prepare for an epic courtroom showdown?
- On a scale of “I want to quit” to “I’m ready to conquer the world”, how tasking was your workday?
- How did your deadlines impact your work speed today? Was it more of a mad race to catch the last bus or a timely stroll to meet up with your Uber driver?
- So, how was your concentration game at work today? How many times did you repeatedly try to suppress the overwhelming urge to unleash your hidden dance moves that are constantly brewing in the depths of your mind?
- Did your workday feel like a roller coaster ride or more like a slow and steady train journey?
- How did your day go? Hope you didn’t spend your work hours wishing for a time machine to go back to the weekend.
- On a scale from “calling the cops to report noise pollution” to “the rhythmic arrival of trains at the station”, how would you rate the level of deafening noise at your factory today?
- Welcome back from work! Hope you blessed your colleagues with your never-ending comedy extravaganza.
- How many times did you have to resist the urge to unleash your inner child and build a fort out of office supplies today?
- In your game of hide and seek with your boss, I’m dying to know who emerged as the ultimate champion.
- How was your first day at work? Did your new office feel like a never-ending maze or more like a leisurely guided tour?
- Did your workday leave you feeling like a superhero or more like a sleep-deprived zombie?
- How many cups of coffee did it take to survive your workday today?
- How many times did you resist the temptation to turn your office chair into a racecar during your workday?
- How many books did you finish to get you by today?
- How many times did you use your best poker face to hide your true feelings during your workday?
- How many times did you use your best acting skills to pretend you were busy during your workday?
- How many smoke breaks did you sneak out to take today?
- Did you have any epic battles with the office printer today, or did you manage to keep the paper jams at bay?
1. How was your day? Hope it was more like a stroll through a quiet park.
When you ask someone this question, you are hoping they had a peaceful day. The question is better directed at someone who seems cheerful after a day at work or someone who you know hardly has a chaotic work experience.
The effect on the person is a quick smile before they respond with a description of their workday.
- ‘Welcome back.’
- ‘Thank you.’
- ‘How was your day? Hope it was more like a stroll through a quiet park.’
- ‘It was. I attended to a few clients today. It was a successful day.’
2. How did your day at the office feel, like a circus or more like a relaxing day at the beach?
Now for someone whose day is always unpredictable, and could be either calm or hectic, this question will give them an ideal option to best describe their workday.
It will bring a smile to their face as they proceed to let you know how their day went.
- ‘How did your day at the office feel, like a circus or more like a relaxing day at the beach?’
- ‘Today was extra. Someone made a wrong order and nobody noticed till the goods arrived. It threw everyone into a frenzy.’
3. You look beat. Did your workday involve any daring acts of heroism?
Some workdays can leave you feeling as if you were heroically saving a young boy from an oncoming train, only to be run over in the process.
Hence, when someone returns from work looking utterly beat, asking them this question is sure to bring a smile to their face, even if it’s just for a fleeting moment.
- ‘You look beat. Did your workday involve any daring acts of heroism?’
- ‘Yeah, something like that.’
4. How many times did you have to resist the urge to crawl under your desk and take a nap today?
Most of the time, especially during slow periods in business, things can get incredibly boring because there’s simply nothing to do.
That’s why these questions can be perfect, as they inject some much-needed humor and lightheartedness into a conversation after an otherwise dull day at work.
- ‘How many times did you have to resist the urge to crawl under your desk and take a nap today?’
- ‘Oh my, I didn’t resist it.’
- ‘What of your boss?’
- ‘He called in sick.’
5. On a scale of “I need a vacation ASAP” to “I can’t wait to resume work tomorrow”, how would you rate your workday?
A day at the office can indeed evoke two contrasting feelings: one that makes you yearn for a vacation, and another that fills you with excitement and anticipation for upcoming or ongoing projects.
Regardless of which end of the spectrum the person experienced, it sure is a fun question that will cause them to smile.
- ‘On a scale of “I need a vacation ASAP” to “I can’t wait to resume work tomorrow”, how would you rate your workday?’
- ‘Oh wow, a chance to finally prove yourself.’
- ‘Exactly! Thanks love’
6. How was your presentation? Did you have a “now you know who’s the boss” moment or a “let the ground open and swallow me” moment?
The tension that accompanies the task of giving a presentation is truly out of this world. Even if you have thoroughly studied the topic, that doesn’t eliminate the feeling of nervousness.
So, when you want to inquire about someone’s day, these questions would be ideal if they had mentioned the possibility of a presentation.
You can be sure that this statement will bring a smile to the person’s face if any of the above is the case.
- ‘How was your presentation? Did you have a “now you know who’s the boss” moment or a “let the ground open and swallow me” moment?’
- ‘I showed them who is the boss.’
7. How was your workday? Did you get to talk with your boss about your concerns? Should I start ironing my legal attire and prepare for an epic courtroom showdown?
Some bosses have a way of making the work environment overly strict and unbearable.
So whenever such is the case of a friend and they decide to talk with the boss irrespective of how impossible it seems, this question will lighten their mood whatever the response they get.
You don’t even have to be in the legal field to make this statement.
- ‘How was your workday? Did you get to talk with your boss about your concerns? Should I start ironing my legal attire and prepare for an epic courtroom showdown?’
- ‘Oh my days, thank you for having my back. Yes, we talked and he said he will see that the changes are implemented.’
8. On a scale of “I want to quit” to “I’m ready to conquer the world”, how tasking was your workday?
When asking someone this question, you are essentially asking them to assess the level of difficulty or challenge they experienced during their workday.
At the same time, you are creating a fun-filled environment while still demonstrating your understanding and empathy.
- ‘On a scale of ‘I want to quit’ to ‘I’m ready to conquer the world’, how tasking was your workday?’
- ‘It was very tasking. I would quit but the bills won’t pay themselves. Glad to be home.’
9. How did your deadlines impact your work speed today? Was it more of a mad race to catch the last bus or a timely stroll to meet up with your Uber driver?
When you ask someone this question, you are inquiring about the influence of their deadlines on their work pace for the day.
By using the comparisons you are creating vivid imagery to capture the sense of urgency or calmness they felt while working on their tasks.
- ‘How did your deadlines impact your work speed today? Was it more of a mad race to catch the last bus or a timely stroll to meet up with your Uber driver?’
- ‘I guess it’s the former. Had to work super fast just to meet my deadline.’
10. So, how was your concentration game at work today? How many times did you repeatedly try to suppress the overwhelming urge to unleash your hidden dance moves that are constantly brewing in the depths of your mind?
This statement is perfect for someone who has a wild imagination and loves dance. They usually can imagine several dance moves and will always move their body wherever they are.
Ironically, a great percentage of the time, they do not know how to dance. So surely, this statement will bring a smile to their face.
- ‘So, how was your concentration game at work today? How many times did you repeatedly try to suppress the overwhelming urge to unleash your hidden dance moves that are constantly brewing in the depths of your mind?’
- ‘You know me too well.’
11. Did your workday feel like a roller coaster ride or more like a slow and steady train journey?
When asking someone this question, you are acknowledging that the person seems to have had an eventful or challenging day. By comparing their workday, you are inviting them to reflect on the pace and intensity of their experiences.
- Did your workday feel like a roller coaster ride or more like a slow and steady train journey?’
- ‘It sincerely felt like a roller coaster ride.’
- ‘Sorry about that.’
12. How did your day go? Hope you didn’t spend your work hours wishing for a time machine to go back to the weekend.
With this statement, you are expressing your curiosity about their day while injecting a touch of humor. By mentioning the idea of wishing for a time machine to go back to the weekend, you are acknowledging the common sentiment of wanting to escape the workweek and return to a more leisurely or enjoyable time.
- ‘How did your day go? Hope you didn’t spend your work hours wishing for a time machine to go back to the weekend.’
- ‘I did, but only because today was uneventful.’
13. On a scale from “calling the cops to report noise pollution” to “the rhythmic arrival of trains at the station”, how would you rate the level of deafening noise at your factory today?
If you ask someone this question, bearing in mind that they work in a factory and that it usually gets so loud, you are asking them to assess the intensity of noise they experienced during their workday using a creative and playful scale.
The former suggests an overwhelming and disruptive level of noise, while the latter implies a more tolerable and even rhythmic background noise.
- ‘On a scale from “calling the cops to report noise pollution” to “the rhythmic arrival of trains at the station”, how would you rate the level of deafening noise at your factory today?’
- ‘Someone should call the cops! Haha, the noise was extra extra.
14. Welcome back from work! Hope you blessed your colleagues with your never-ending comedy extravaganza.
This question playfully acknowledges their sense of humor and expresses your hope that they brought laughter and amusement to their colleagues during the workday.
By using the phrase “never-ending comedy extravaganza,” you are highlighting their ability to consistently bring joy and entertainment to those around them.
- ‘Welcome back from work! Hope you blessed your colleagues with your never-ending comedy extravaganza.’
- ‘You know me too well.’
15. How many times did you have to resist the urge to unleash your inner child and build a fort out of office supplies today?
This is a perfect question for someone who expressed that their day was boring. Usually being idle makes one contemplate all creative possibilities.
After all, who wouldn’t want to add a touch of adventure and whimsy to an otherwise uneventful day?
- ‘How many times did you have to resist the urge to unleash your inner child and build a fort out of office supplies today?’
- ‘Who said I resisted it? Haha.
16. In your game of hide and seek with your boss, I’m dying to know who emerged as the ultimate champion.
If you are looking for a witty statement for someone who is avoiding their boss, this is your best bet. It implies a sense of playfulness and perhaps some level of strategic maneuvering or evasion.
- ‘In your game of hide and seek with your boss, I’m dying to know who emerged as the ultimate champion.’
- ‘I did! Where’s my trophy?’
17. How was your first day at work? Did your new office feel like a never-ending maze or more like a leisurely guided tour?
When asking someone the question, “How was your first day at work? you are inquiring about their initial experience at their new job.
By using the metaphor of a never-ending maze, you’re alluding to the potential challenges, uncertainties, and complexities they may have encountered during their first day.
On the other hand, the idea of a leisurely guided tour suggests a more relaxed and well-structured introduction to their new workplace.
- ‘How was your first day at work? Did your new office feel like a never-ending maze or more like a leisurely guided tour?’
- ‘Hmm, more like a guided tour. Everyone was friendly and willing to put me through.
18. Did your workday leave you feeling like a superhero or more like a sleep-deprived zombie?
By using this playful analogy, you create a light-hearted atmosphere where you compare the impact of their workday on their energy levels and overall mood.
On the other hand, the reference to a sleep-deprived zombie suggests exhaustion, and perhaps a challenging workday.
- ‘Did your workday leave you feeling like a superhero or more like a sleep-deprived zombie?’
- ‘Maybe both. Completed my assignment but it took all my strength.’
19. How many cups of coffee did it take to survive your workday today?
By asking about the number of cups of coffee, you’re teasingly suggesting that their workday was challenging or demanding to the point where they needed a significant amount of caffeine to keep going.
By using this playful inquiry, you create a lighthearted and relatable atmosphere.
- ‘How many cups of coffee did it take to survive your workday today?’
- ‘Maybe a perfect ‘1100’ to keep me going.
20. How many times did you resist the temptation to turn your office chair into a racecar during your workday?
Ah, the temptation to turn an office chair into a racecar! It sounds like you’re asking about playfully imagining the excitement of racing while at work.
By posing this question, you’re light-heartedly acknowledging the potential for boredom or monotony during the workday and the desire for a little adventure or fun.
- ‘How many times did you resist the temptation to turn your office chair into a racecar during your workday?’
- ‘I had a chair race with my colleagues.’
21. How many books did you finish to get you by today?
By asking this question, you’re playfully acknowledging the role of books as sources of inspiration, knowledge, or escape to them. It provides an opportunity for them to express their love for reading, and share whether they relied on books to get them through the day.
- ‘How many books did you finish to get you by today?’
- ‘Finished 2, and started another one.’
22. How many times did you use your best poker face to hide your true feelings during your workday?
By using the phrase “poker face,” you playfully allude to the skill of maintaining a neutral expression to hide one’s emotions, just like in a game of poker.
Overall, this question serves as a fun and engaging way to inquire about their workday while acknowledging the potential need for composure and emotional control in professional settings.
- ‘How many times did you use your best poker face to hide your true feelings during your workday?’
- ‘All the time! never to be caught off guard.’
23. How many times did you use your best acting skills to pretend you were busy during your workday?
Some workdays can be boring and uneventful. By pretending to be busy, one removes the chances of appearing unproductive.
By asking this funny question, you playfully acknowledge the need to create the illusion of busyness, perhaps when a supervisor, HR, or the boss is within sight and there might not be a lot of tasks or assignments at hand.
- ‘How many times did you use your best acting skills to pretend you were busy during your workday?’
- ‘Just once! When my supervisor came to collect a file.’
24. How many smoke breaks did you sneak out to take today?
By using the phrase “sneak out,” you playfully acknowledge the act of taking breaks without official permission or without adhering to designated break times.
- ‘How many smoke breaks did you sneak out to take today?’
- ‘A lot! Didn’t count.’
25. Did you have any epic battles with the office printer today, or did you manage to keep the paper jams at bay?”
This question playfully references the common struggle many people have with office printers and their notorious paper jams. It invites the person to share any amusing or frustrating encounters they had with the printer during their workday, creating a light and relatable atmosphere.
- ‘Did you have any epic battles with the office printer today, or did you manage to keep the paper jams at bay?’
- ‘Oh yeah! It was a battle indeed.’
Final note
Feel free to use these funny questions and statements to bring a smile to someone’s face and make conversations about work more enjoyable! Sometimes, people need someone to ask them how their day went at work but they do not have any, you could help with that.