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Feel shy and awkward? Or just fear being shy and awkward?
You’re not alone — 40 to 45 percent of all adults consider themselves to be shy, according to Bernardo J. Carducci, Ph.D. Being an introvert can make it hard to start conversations, since there are often many things shy people tend to worry about when approaching someone new, like the potential for awkward silences, embarrassing moments, and that horror of all horrors, pointless small talk. To make things a little easier on yourself, it can be helpful to break the ice with funny conversation starters (just keep topics in the clearly "safe for work" category).
Conversation starters can be a useful tool in a work setting. Remember to keep the conversation positive and avoid topics that can cause stress or negative feelings. Some these topics to exclude are salary, politics, religion, age, and gossip. Instead focus on questions that bring joy and positivity to your work environment. Here are 100 ideas to get you started:
People love to talk about themselves, and so asking a question is a good way to break the ice and get the other party going (which means less work for you!). Here are a few examples to get you started:
Everyone’s a foodie these days — they may tell you about the first time they tried a certain type of food or followed in Andrew Zimmern’s footsteps.
This can be a great way to gauge their sense of humor (and how far you can take things).
This spin on #2 is a little more specific.
This is a way to find another possible talking point, as well as feel out more about their sense of humor.
It’s a personal question, but not too personal, and it has the potential to result in a funny anecdote — perfect icebreaker!
Openers like this one are especially great at networking events and can lead to an exchange of stories.
Everyone has experienced a dining fiasco and sharing can help break the ice.
This is a similar alternative to #7—and something everything has an opinion on.
Questions like this one are whimsical, childlike, and thought-provoking all at once.
Hopefully, the irony of the question won’t be lost on your potential conversation partner.
Even people that don’t follow the daily antics of celebrities will likely have something to say about this icebreaker. A similar option: “If you could be at a dinner table with any five celebrities, who would they be and why?”
People love conversational topics that let them reminisce about their childhood. Hopefully, this will bring them to the past, not present.
Most people have fantasized about having a different life, so it's a related way to open a conversation.
Whether the response is silly, earnest, selfish, selfless, or just plain weird, this prompt is bound to get people talking.
Everyone has a favorite show, and probably one they've seen many, many times. This question can also help you establish common ground.
Bad gifts can make for great stories later on.
Kids say the darnedest things.
You'll learn a lot about how someone perceives herself.
The response may shock you.
This can kick things off well, especially for animal lovers.
Dog, cat, bear, rabbit...whatever the answer is, it can tell you a lot about a person.
Yes. Yes, there is.
A Bond villain? Norman Bates? Freddy Kreuger? Voldemort?
Luke Skywalker or Wonderwoman?
Everyone wishes they could make small changes in the way the did something or behaved.
This can get a little dark, but most people have an opinion.
This is universally appealing except for those who may be lactose intolerant.
...As opposed to this one, which works for everyone.
They just can't answer "infinite wishes."
From flight to invisibility, the answers are endless.
At least now you'll know not to do it.
This may make people think.
This question can open some serious discussions.
It makes you think about language.
It makes you think about math.
People have a lot of different opinions about how society functions—and how it misfunctions.
Late night ice cream, romance novels, anything—this humanizes your acquaintance.
This not only reveals personality but also literary tastes.
Who doesn't have a crush on a fictional character?
Maybe you can fit your whole fist in your mouth.
It could be good.
Time to relive it.
Some people have pretty weird ones.
Try to get her to show it to you.
And if so, which one?
Unfortunately, there have been some untimely cancellations.
The Bachelor or Survivor?
You can't always control what people call you.
But if you get creative, maybe you can change that!
You'll find out what kind of people your acquaintance admires.
Is it ethical if you have a very good reason?
Travelers might not mind it too much.
Some people love a grand gesture. Others hate them.
It could be something really strange...or pretty normal.
You don't have to be a picky eater to avoid some foods.
Come on—everyone's done it.
This one gets the other person to think.
Sometimes, it's just time to leave.
Some people are natural marketers—and storytellers.
And did you delete it?
And did you get it back?
You can still be humorous while digging deep. These prompts will get the dialogue flowing while prompting your new acquaintance to think.
(Sometimes people are more likely to divulge their secrets to strangers than friends and family.)
Time to delve into dreams and goals.
Everybody has a flaw—and chances are they know it.
Useful or strange, it's something to consider.
If they're willing to admit it, of course.
Some people think about it.
If yes, does anything we do matter?
Does someone know the answer? Let me know.
And on the same note:
Makes you wonder.
Maybe there's a "right" answer to this one...or at least a debate in there.
A little dark, but something about which people might have an opinion.
Hopefully, the answer is yes!
This one can get a real debate going.
Everybody has a funny story that serves as their go-to at parties or job interviews and first dates. Instead of waiting to slip it in later in the evening, use it as a conversation opener. Just adapt it to fit the situation — i.e., so that you’re never naked or doing something illegal in said story. And keep it short and sweet so that your conversation partner has a chance to share their favorite gem, too.
Jerry Seinfeld became rich and famous for his observational style of humor. Follow suit and find something funny to comment on — just so long as your observation is not at someone else’s expense. It’s never good to make a first impression as a “mean girl.” Instead, start a conversation by saying something about the situation that you find yourself in, like a comment on what’s for dinner, the temperature in the room, etc.
If all else fails, ask if they’ve seen the latest viral humor video or who their favorite comedian is. Asking an open-ended question about funny people is a great way to nudge your small talk in a humorous direction.
There’s nothing like a little self-deprecating humor to help put others at ease and leave those awkward silences in the dust. To start a conversation this way, look for ways to contextualize poking fun at yourself; if you attend a formal event, for instance, and are underdressed, cracking a joke about how overdressed you are works.
Try to keep this light if you attempt the game. For instance, you might dare someone to order a glass of milk at the bar or ask someone to reveal an embarrassing secret from childhood.
Read the room. Does it seem like a fun crowd? Are people willing to poke a little fun at themselves? This game can certainly get the party going and help you get to know one another a little—or a lot—better.
This article reflects the views of the author and not necessarily those of Fairygodboss.
Carly Zinderman is a freelance content provider specializing in lifestyle including travel, food, fashion, beauty, home decor, entertainment, health, fitness and wellness, and green living.
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