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Dating Triumphs and Tragedies
by Nicole Roberge

20 Questions for Your Date

I recently talked to a (married) friend about my dating life, and how I had discovered that it always seems to be me asking all the questions, which makes it hard to get to know someone, or rather, for them to get to know me, and ultimately, form a connection. She, “Georgia,” told me that she had read a book once filled with questions to bring on a date that are a fun and interesting way of getting to know another person. While I might be a little wary of bringing a book on a date and again, “interviewing” someone, it was a cute idea. It reminded me of teenage sleepovers and asking your friends questions in the back of magazines, but different of course. Now it was with a guy who you hoped there might be some kind of chemistry with.

But there was a spark to this idea. Some people go on to dates with a list of questions in mind:

» Where are you from?

» What is your family like?

» What do you do for a job?

» What are your hobbies?

» Do you have any pets?

» Isn’t this dating thing just draining?!

Yeah, you get all those questions out of the way to know the background of a person, to know the basics. The “getting to know you” can establish what you might have in common in how you were raised and how you live your lives now. But in order to get to really know a person, it can take a little time. Over a few dates, you can pick up on little cues like what they order for meals, how they treat their server, how they treat you of course, body language, and what they are inclined to talk about. But, what if you were to ask them some random fun little questions that might get his mind going, conversation rolling, and initiate a few laughs? It might be just what the date needs, as you learn more about each other while having non-boring conversation, and lead to a second date.


I opened my mailbox the other day to find a little package from my friend Georgia with a cute note about dating, and it included the book “Coke or Pepsi? 1000 coke or pepsi questions 2 ask your friends!” by Mickey Gill and Cheryl Biddix. Curious, I opened the pages and found myself reading questions and being amused by the answers, or really having to stop and think about the answers.

The more I looked at the questions, I thought: These are things that I want to know about a potential date. They can be quite revealing in an unsuspecting way. A simple answer of “Strawberry Frosted” to “What is your favorite donut?” might mean he has a sweet tooth, likes strawberries, or is a Simpsons fan. Of course, you don’t want to read too much into the answers, but this could be a really fun way to lighten up a date and engage in funny conversation, and overall just feel relaxed. Or, once you have been dating a while, sit down and each fill out the questionnaire and then share the answers. You might be surprised what you hear. If you’re really risky, and in the advanced stages of a relationship, you can try and guess his answers. But remember, these are personal in a way—preferences that might go back to childhood—you may not always know what he is thinking.

So just for fun, I will put some sample questions here, and as if we are on a date, I will answer them too. Give you a little insight into my wacky ways. Hey, no else is asking right now. Just kidding……..

Milk or Dark Chocolate? Dark Chocolate

What kind of shoes are you wearing? None. I hate shoes. Which is probably why I got stung by a bee on my foot the other day. Ouch.

Favorite place you’ve visited? London. And I’d like to live there for a bit someday.

Best beverage? Pumpkin Spice Latte…too bad it’s seasonal.

Which would you try—skydiving, rappelling, or scuba diving? Skydiving.

Elementary school—bully or bullied? Neither, quiet and shy.

Ever broken a body part? Yep, my wrist…when I fell off my bike, playing a stupid game in my yard.

Iced Cubes of Crushed Ice? Neither, I don’t like ice.

Do you believe in Big Foot? I liked Harry, from Harry in the Hendersons. Good movie.

Did you run away from home when you were little? My sister and I would sneak down to my neighbor’s house. We though we were clever, but both my parents and neighbor always knew first.

Favorite costume you’ve ever worn? Dorothy Gale from the Wizard of Oz.

What scared you as a kid? On Christmas morning, I was afraid Santa might be waiting outside my door, so my sister would always open it first and get my stocking. Maybe I just didn’t want to get out of bed?

Any advice for a 5-year-old? Stay 5.

Those are just a sampling of some questions, and of course, the answers are different for everyone. But it’s basically just the idea that you don’t have to stick to the same standard questions on dates. Mix it up a little. Sure, ask about his family and his job and hobbies, but ask what his favorite childhood memory was too. It might make him a little nostalgic and happy that you asked and cared. People like to share their good memories, and also their opinions on bizarre and funny things, and then when they argue to prove their opinions on those things, it can be funnier. “Coke or Pepsi?” He might be mad that Root Beer isn’t included, and then you might get an earful, so just be prepared…for a cute argument that will probably make you smile and happy that you asked the question. The standards of dating have changed so much, so should the questions!

Dating Triumphs and Tragedies is published every Sunday by Online Dating Magazine columnist Nicole Roberge. She can be reached at

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