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? →

Truth be told, I find this question nearly impossible to answer. How could you possible choose between the two? I think the unfairness of the question is why I’m drawn to it. So much of who I am comes from international experiences… But if I absolutely gun-to-my-head had to pick, I’d live in the circle with the 150-mile radius. I think that reflects my belief that you can always go deeper where you are. You can discover a new world by getting to know your neighbors. And if you can build community with those around you, you’ve done your part to bring about peace in the world. At least that’s how I feel right now… This is a great question to find out how someone thinks about travel and how they value the sense of place. Continue reading Which would be worse: having to leave the country and never return, or never being able to travel more than 150 miles from where you live now? →

There are family nicknames, sports team nicknames, nicknames from camp or school or work… And nickname origins often involve a personality trait/quirk or a slightly embarrassing story. Even a short answer to this question gives you tons of conversation starters. “When I played soccer, my teammates called me “Gumby.” Why Gumby? How old were you when you played soccer? What position did you play? Do you still play any soccer? Do you miss organized competition? Have you ever seen an actual episode of Gumby? Continue reading Have you ever had a nickname? →

The first book I ever re-read was The Hatchet by Gary Paulsen. I was maybe 12 years old. I loved that book! About survival, resourcefulness, coming of age… I’d probably start reading it again right now if I had it. If someone invests all the time necessary to re-read a book, that book has gotta say something about them as a person, right? (I don’t know what it would mean exactly. But, something!) Plus, as an English major I just love books and readers and re-readers! 100 bonus points to your date if he/she is a re-reader! Continue reading Do you ever re-read books? What book have you read the most times? →

This is a great question. It’s not about one-upmanship; it’s about being sympathetic and hearing out a good story. Life is full of broken bones, cuts, and surprise trips to the emergency room. Let’s talk about how we got into all those messes! This question could be asked of lots of people, but it seems like a great date question in particular. (I don’t always answer the questions myself but I just have to share that one of my best friends and I played a lot of paintball in high school and early college. My best friend’s roommate’s mom’s boyfriend (seriously) tagged along with us one time. We lent him one of our extra paintball guns. Super nice guy. So nice he wanted to help clean the gun at the end of the day when we were all relaxing in the parking lot of the paintball field. We said it was fine, we’d handle it. He kept fiddling, removed safety features, and accidentally shot me RIGHT between the eyes from less than 3 feet. Didn’t lose my eyes but came REAL close. The resulting welt/wound was hideous.) Continue reading What’s the worst injury you’ve ever had? →

You know there’s that thing people have been telling you for about as long as you can remember. “At first I thought you were really serious.” (I get that one a lot.) Or “No way you’re 33, I thought you were like 15 years old.” (My older sister gets that one all the time – chalk it up to being Filipina and 5’2″.) “So do you surf?” (My friend who grew up on Maui hears this one often. He doesn’t surf.) People are eager to dispel the common misconceptions about themselves. That’s what makes this a great date question. It gets you past the surface level and allows you to start relating to the other person in a more complete way. Continue reading What is the one thing people always assume about you? →

This can be a really great question but the timing matters a lot. This isn’t a great first date question because if you ask it on a first date you’ll get the response that people *think* they should be giving. Oh, well you know, I’d work out in the morning, spend time outdoors with my friends, read a novel etc etc… A first date will probably answer this like an interview question. But on a fifth or sixth date, the time and trajectory of your budding relationship allows for more authentic answers. I’d sleep in until 11am. I’d make a gigantic breakfast burrito. I’d go for a walk with my mom. (As an added bonus, the answers to this question after the fifth or sixth date will give you great ideas for the seventh and eighth dates.) Continue reading What would go into a “perfect” day for you? →

Is your date a private person? Or would he enjoy some aspect of the limelight? Would he want to be the center of attention in every room? Or maybe he’d want to be famous by an online username only. This question helps you understand what kind of recognition, if any, energizes a person. Continue reading Would you like to be famous? In what way? →

This is actually more personal a question than it might seem at first. Like it or not, our phones contain more and more details about us with every passing day. So only use this if the date is going well. If it is, this question is playful and can help you both let your guards down. Continue reading What’s the last picture you took on your phone? →

NYC? Boulder? Madrid? City of choice can tell you a lot about a person and their hopes for the future. This question is a door. You might get to know what kind of setting energizes a person. You might learn about family members and the importance of proximity. You might discuss what’s not to like about the city you’re in at that moment. This question feels very approachable while still offering depth. Continue reading If you couldn’t live here in [City], where would you choose to live instead? →

Not rocket science. This one is just a solid question that could open up discussion about things happening at work, church, with family, friends, vacation… Continue reading What are you looking forward to most in life right now? →

Simple, disarming, and likely to lead to a fun conversation. Just make sure that you sympathize instead of mock. And make sure that you share something you’re really bad at, too. Continue reading What is something that you’re really bad at? →

This is the premise behind an interesting online experiment called the Listserve Project. Joining the Listserve makes you eligible to be the one person chosen each day to address the entire group. And you can say almost whatever you want. This question can show you what someone cares about (self-expression, giving advice, promoting something…) and it can show you what he thinks should get more attention in the world. Continue reading If you could send an email to 1 million people that they would HAVE to read, what would you write in it? →

TV and movies are great, but the way we come across really substantial and life-changing ideas is primarily still via writing. This can come in all mediums – a book by Tara Brach, the WaitButWhy blog, an article on Medium. So this is a great question to ask someone you’re trying to get to know more deeply. Also, when you start asking this question you’ll want to be able to answer it yourself, which means you’ll start reading more too. Continue reading What are you reading at the moment? (Book, magazine, blog, essay, article online…) →

Potentially kinda risqué but it’s a fun question.  Just don’t be a creep about it.  You’re better than that. Continue reading If you could make your pointer finger taste like anything at all times, what would you make it taste like? →