Dang! I just made up a brand new category for this single question. I don’t normally make new categories until I have at least 5 questions but I couldn’t resist. This one is too good. (And I’ve been going to too many weddings in the last several years not to share it.) So you know how at some weddings you and your +1 are seated at a table for dinner with people you only kind of know? And you know how conversation that involves everyone at that table is sometimes hard to get going? Well next time, just wait for that lingering silence and then throw out, “Hey, if you had to give a toast tonight, what story would you tell about [Name] or [Name]?” You’ll have the tightest table at the whole reception faster than you can say, “Cupid Shuffle.” You’re welcome! Continue reading If you had to give a toast tonight, what story would you tell about [Name] or [Name]?
The animal could be your own pet. Or it could be a deer you saw on a hike. It could even be a killer whale from that crazy Blackfish documentary that blindsided Sea World and forced them to start phasing out their orca shows. The biological diversity on our little planet is truly staggering. Humans plus, oh you know, just a couple million other species. So what’s one lesson that you’ve learned from interacting with or observing an animal? Continue reading What’s one thing you’ve learned from an animal?
I grew up in Southern California (310 represent, baby!) and I’ve always loved the beach and the ocean. I learned to surf as a Junior Lifeguard when I was 10 years old. I’m not great, but I do love it. When I moved to North Carolina it meant living as far from the ocean as I’d ever lived. That was really unsettling for me. So when I got to NC, one of the first things that I started looking for on Craigslist was a surfboard. As soon as I found a good deal on a decent board, I snatched it up and IMMEDIATELY felt a sense of relief wash over me. Security blanket effect, for sure. In the five years that I’ve owned it, I’ve surfed it three times total. In fact, I’ve surfed way more often on my old boards at home when visiting my family back in SoCal, haha. But I’m always going to own a surfboard out here in NC, regardless of how little use it sees. I realize that, logically, this makes no sense. But I don’t care. And I have a feeling I’m not alone. But you tell me… Am I? Continue reading What’s something you own because you just like the idea of having it (more than you actually use it)?
If you’re just having no luck getting your kid to answer ANY question (fun, unusual, or otherwise), give this one a shot. Sara Ackerman in the Washington Post writes that when she asked her daughter “Do you want to hear about MY day?”, her little girl was indeed interested in hearing about mom’s meetings and the jammed printer. And after Sara shared about her own day, her daughter, “like she’s taking her turn in a game of Go Fish” opened up about what she’d done that day. The article explains the genius behind this question better than I can. Check it out right here and let us know if this finally gets your gradeschool kid talking! Continue reading Do you want to hear about my day?
Seriously, is there anything better than a deep, rejuvenating, re-centering night’s sleep? Outside of your own place, where do you go to get that? Some people swear by the sleep they get while camping. I’ve heard of grandparents’ houses being another location that lulls people into deep sleep. One of my best friends has a back bench in his big van that can turn into a full bed. He raves about the sleep in there. Where do you sleep best?
Continue reading Outside of your own place and your own bed, where do you sleep best?
Perfect question to ask your siblings because, together, siblings come up with some weird ish, man! My sister and I made up a road trip game called “Mr. Brown”. We were probably 5 and 6 years old, respectively. This is how “Mr. Brown” game would go: Someone would ask, “Hey, do you wanna play Mr. Brown?” The other person would say yes so we’d find this one pillow that my mom always put in the car for us during road trips. It was a square, off-white pillow with a thousand small fabric tassels around the edge. We’d each yank off one tassel and proceed to chew on it like gum while saying, “Mmm! Yum! Mr. Brown.” That’s it. That was the whole game. W.T.Effff? The tassels tasted salty and starchy and disgusting. There was no winner. It wasn’t even a game. But we still played it every road trip. Don’t ask me… Continue reading Do you remember us making up any games as kids?
Kids aren’t exactly known for long-term planning. So it’s always interesting to find out what single thing was so desirable in your young life that it got you to forego candy and arcade games and whatever else so that you could save up some dough. For me, the 1991 release of the Super Nintendo console made me quit my 7-11 beef jerky and gummi bears habit faster than you could say “Hadouken!!” I also sold the original Nintendo console that had been gifted to my sister and me (along with all the original Nintendo games I’d gotten from past birthdays and Christmases). $200 bucks and a few months later and I was on my way to Toys R Us, boyyyy! Continue reading What was the first thing that you saved up your own money to buy?
This question is aimed pretty squarely at the older Millennials out there. Remember AIM? (AOL Instant Messenger) I’m an old Millennial myself and I can say that all of my peers are at least a little bit embarrassed about their AIM names. Mine was PBDiy1polo. “PB” for “paintball” because I played a lot of it in middle and high school. “Diy” for my last name. The number 1 and “polo” because I was a water polo goalie and goalies are always assigned the number one. Haha. It’s funny to remember this stuff! This is a great date question because it’s a throwback, it’s a bit embarrassing/vulnerable, and it actually tells a lot about people in most cases! (The question can be modified for anyone by asking the more general “What was your first online screen name?”) Continue reading What was your AIM screen name?
I spent a lot of time this past weekend with the two-year-old son of one of my close friends from church. I saw the little guy on the first day he was born and I’ve seen him several times a month ever since. This is the first time in my adulthood that I’ve watched an infant develop like this. The little dude is just hilarious now. In the past 6 months he’s become so much more verbal and has started to show so much more of his personality (loves throwing frisbees and bouncing balls, is silly and active, but is also cautious with new things…) Anyway, as he cracked up about the frisbee game we were playing yesterday, I wondered… “Is there even a chance of him remembering this?” My earliest memory is from four years old; it’s of my sister and I playing in our apartment complex. I can’t remember a single thing before that. Can you? Continue reading What is your very earliest memory?
And in what area of your life are you okay with even being BELOW average? And in what area of your life do you KNOW that you need to be above average in order to be able to sleep at night? This trio of questions is a guaranteed conversation starter with any group of friends. I know because I’ve tested this a few times now and I’ve watched some interesting things happen. You definitely will learn what skills and what relationships your friends prioritize in life (that’s number one and is interesting all on its own). But inevitably some people will pick something silly to be below average at (like juggling or ventriloquism or some other thing they don’t even really do). Someone will ask how to define the word “average.” Someone will probably ask if “average-ness” in this hypothetical situation is a matter of skill or of effort. The conversation really takes off! And it’s hard to say all the directions it could go. You ask it and let me know what happens! Continue reading In what area of your life are you okay with being just “average”?
Ryan and Mike have been my best friends since 1st and 2nd grade respectively. Ryan and I clicked because on the 1st grade playground, I liked how he could kick a soccer ball really high into the air. Mike and I connected because in 2nd grade I was way jealous of the skinny crayola markers he owned (you know the fine-tipped ones with better colors like teal and gray that were way cooler than those clunky “normal” markers?) and so I made it my mission to sit next to him. Haha! Over 25 years later and these guys are still among my closest friends and brothers for life. Thanks to soccer ball hangtime and skinny crayola markers! It’s so stupid and random! And also somehow sacred because of that. Continue reading Which of your friends has been in your life the longest and what initially did you bond over?
At a friend’s wedding earlier this year, I helped lift him (and the chair he was in) into the air as people danced and clapped. Jewish tradition, right? I bet you knew that. I did too. But why did we do that exactly? With the chair and all? I mean, what’s the significance? No idea. The same goes for the Oktoberfest beer I just drank. What is Oktoberfest about, again? Apparently it started as a public wedding celebration in 1810 for Kronprinz Ludwig and Princess Therese of Saxe-Hildburghausen. Huh. Thanks Wikipedia! But I’d be lying if I told you I knew that 2 minutes ago. What’s a tradition you’ve participated in without knowing the larger significance? (And when you come up with an answer to that, I challenge you to learn more about it! Come on! Do it for Princess Therese of Saxe-Hildburghausen!) Continue reading What’s a tradition you’ve participated in without knowing its significance?
Every few years do you become restless with your work and wonder if you should switch to something that makes more of a difference in the world? Do you exercise religiously for 3 months straight and then hardly at all for the next 15 until you sternly recommit to the importance of working out again (for 3 months)? Are you drawn, continually, to writing? (Guilty on 3 counts over here in my corner.) These are patterns that I see in my life. What are yours? They could be any range of things. Maybe you’re repeatedly asked to take leadership roles. Maybe you’ve had a string of bad bosses. Maybe you feel a strong urge to travel abroad every few years. These cycles are not necessarily positive or negative; they’re just patterns. And when it comes to self-awareness, I think patterns are worth finding. Continue reading What circumstances tend to repeat themselves in your life?
So have you heard of the website Fiverr.com? It’s an entire online marketplace of people who will deliver digital work to you (according to your specifications) for five bucks. Want someone to write and perform a rap song about your cat? Want someone to prank call your friend in a Donald Trump voice? Need someone to translate your poem into Spanish? Or could your business use an updated logo? People will do all of that on Fiverr for, yup, five bucks. If YOU absolutely had to convince twenty strangers to buy a service from you for five bucks, what would you do? (I like this question for two main reasons: 1) It’s like a “What’s your hidden talent” question but more interesting because the talent has to be marketable, 2) I always love helping people create side hustles for themselves and this question is a first step to your side hustle idea! Everyone needs a side hustle!) Continue reading If you had to convince twenty strangers to buy a service from you for $5 bucks, what would you sell?
Growing up in Southern California, I’d never actually experienced very distinct seasons. But after living several years in North Carolina, it turns out that I love fall. All summer in NC, it feels like the sun is sitting down closer in the sky and steaming everything on the ground. This makes the cooler crisper temperatures of fall such a welcome change. And it makes my bike commute to work a real pleasure. Fall in North Carolina – that’s where it’s at. (But I’ll always love summer in Southern California, too. Oh and also, Christmas time in Manila with all my extended family. It’s hard to choose!) Continue reading What is your favorite combination of season and place?
Would it be a workshop on how to get along with in-laws? Or maybe a workshop on how to talk about finances? Or perhaps one on juggling two careers? Basically, what relationship skill/hack/ability could you as a couple offer other couples? Where does your relationship feel strong in a way that others could benefit from seeing? If Emily and I offered a workshop to other couples, one subject could be about how to survive long term long-distance situations. After 4.5 absurd years of doing long distance from 2007 to 2011, we’d have a lot to offer couples struggling with distance. What would you and your partner teach? This is a great question to ask your S.O. directly but it’s also a really interesting one to ask another couple. Continue reading If you and I taught a workshop about one of our particular strengths as a couple, what would we teach?
This is a question to ask yourself when someone else you know is sick. If you’re mowing your lawn this week, or making a big batch of burritos for your family, or borrowing some good books from the library, then consider just going ahead and doing the same for your friend while you’re at it. There’s power in just DOING because many people will not ask for help even when they need it. Or they won’t even have the time/energy to figure out what exactly in their daily life needs attention. (One big caveat, however: There’s a delicate balance to maintain here. For some things, it’s very important to ask first — especially if it’s about visiting a sick person at home or in the hospital. But for other things, saying “Let me know if I can help” is much less helpful than just doing things unprompted. Everyone is different, though, so it’s up to you to figure out what is actually beneficial for your friend.) Continue reading What am I doing for myself this week that I could also do for [name]?
This question combines two of the things I contemplate most often: work and peak experiences. Work isn’t just what you do to pay your bills; it’s what you do with the best years of your life. It’s where you are spending your life’s best energy, best years of health, and most creative days. Your work should really matter (at least to you). And as far as peak experiences go, I’m very interested in the moments that people feel most “in the zone.” It’s my theory that maximizing the number of peak experiences in any given community is a pretty great way to improve quality of life for everyone. Mashing these two things together yields this question: When was the last time you left work feeling on top of the world? I like this question as one you can ask your employees or team. But it’s also a great question to ask your friends. Asking it can lead people to more peak experiences at their current jobs or it can lead them to different work entirely. Continue reading When was the last time you left work feeling on top of the world?
No seriously. Have you read it? Here’s a direct Amazon link. Do yourself a favor and pick up a copy. Trust me. I consider this question a good one to ask for the sake of the world for two reasons. 1) If you read this book you are 100% guaranteed to become a better human being for yourself and everyone in your life. 2) If a bookstore were classifying “The Gifts of Imperfection,” the staff would put it in the “Self Help” aisle. I HATE the stigma that surrounds self-help in general. I know not all of it useful, but SO MUCH of it is beneficial and life-giving and amazing. This includes books, talks, seminars like The Landmark Forum, sessions with a counselor/therapist/life-coach, the list goes on… Bringing up this question helps chip away, ever so slightly, at the accumulated stigma around “self help.” Life is full of challenges. Why not benefit from the really smart people who have trained and thought a lot about how we can all be better? Continue reading Have you read “The Gifts of Imperfection” by Brene Brown?
Sleeping bags. Every time. Especially if, instead of being zipped up, they’re unzipped and laid out flat. I remember napping on sleeping bags like this as a kid. I remember resting on sleeping bags like this whenever I was sick and staying home from school. My sister and I would also often play games with sleeping bags – we’d use sleeping bags as “safe” while playing tag or we’d use them as the roofs of forts. Also, we called them “seeping bags” a lot of the time so even saying that now makes me feel like I’m 7 years old again! What makes you feel like a kid again? Continue reading What makes you feel like a kid again?