The 55 Best Questions To Ask To Get To Know Someone

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Any upcoming travel plans?  Montréal, Québec!

What brought you here?  To Toronto?  Love, school and work … in that order.  He and I broke up six months after I moved here, but I stayed for school and work.  ‘Tis home now …

How do you two know each other?  I know everyone.  I’m *that person* who gets into the elevator and talks to you.

When you’re not working, how do you like to spend your time?  Anything inside or outside.

What are you reading currently?  We Are Never Meeting in Real Life by Samantha Irby.  I love her blog Bitches Gotta Eat!

What’s the first concert you attended?  I think it was AC/DC but I don’t actually remember … Kathy, do you?

Where do you most hope to visit?  Anywhere in Europe.

What’s your favorite book?  The Kama Sutra

What’s your favorite 90’s show?  Seinfeld, Friends and Fresh Prince of Bel-Air

What’s the best Halloween costume you’ve ever had?  The Fox!

What’s your dream job?  Fighter pilot

What’s your favorite word?  Fuck

What was your first job?  Bank teller

What’s one thing you’re excited about that’s coming up in 2018?  Book publishing!

What was the worst job you’ve ever had?  Bank teller

What is your most-used emoji? crazy

If you could win an Olympic medal for any sport, real or fake, what would it be?  Equestrian jumping, dressage or figure skating.  Or maybe snowboarding!  Or having sex like a porn star.

If you could change your name, what would it be?  Heather.

What movie or TV show title best describes your week? Chicago Fire.

What was your favorite subject in school?  Law.

What’s your hidden talent?  *Ahem* Clears throat …

If you had to eat one thing for every meal going forward, what would you eat?  Rare Beef Pho.

If someone were to play you in a movie, who would you want it to be?  Some no-name redtube porn star.


If you could spend a day in someone else’s shoes, whose would they be? Why?  Meghan Markle … because I think Harry is hot.

What’s one thing your mother/father taught you that completely changed your life?  My Dad gave me the gift of wonder, the love of the arts and science, and a spark of spirituality.

What’s been on your mind lately?  Wondering if I am cancer free.

What’s the first career you dreamed of having as a kid?  An architect.

What’s the last text you sent?  I want sushi.

What’s one of your favorite memories?  Helping a horse give birth to a breech foal.

What’s one thing about you that surprises people? I absolutely love sex.

Who, or what, was your biggest teacher?  My Mom and God.

What was something you’ve done that made you feel extreme happiness?  Saving lives.  I volunteered in an Emergency Room in downtown Toronto.  One stormy night there was a multi-car accident on the highway.  One of the doctors asked me to go with him to the helicopter landing pad on the roof to assist.  I did CPR on a patient all the way to the OR and saved his life.

Knowing what you know now, what advice would you give your 18-year-old self?  Marry Richard.

If you could instantly become an expert in something, what would it be?  I wish I could sing.  I could totally be a Rockstar! 

What does success mean to you?  I used to say multi-millionaire … but I know many who aren’t happy.  I want health, some wealth and happiness for everyone.

What’s the best piece of advice you’ve ever been given?  Don’t take anyone’s advice.

Where is your happy place?  My spirituality or my sexuality.  It’s a toss up.

If you could invite 3 people, dead or alive, to a dinner party, who would they be, and why?  My Mom and Dad.  My father died before my son was born.  I’d love for them to meet and to have Christmas dinner that my Mom cooked just one more time.  I miss them both.  Time After Time.

How can someone win a gold star with you?  Buy me one single tulip.

What energizes you and brings you excitement?  People.  I am an extrovert.

What qualities do you value in the people with whom you spend time?  Loyalty, kindness, non-judgemental and supportive.

For what would you be famous?  Writing erotica.

What does your dream day look like?  Winning $70M on the LottoMax and building a Dog Tales type sanctuary.

If you didn’t have to sleep, what would you do with the extra time?  *Ahem*  Clears throat …

What’s your guilty pleasure?  Reading and writing erotica.

At what job would you be terrible?  Poker.  I have no interest in gambling and don’t have a poker face.  If I think you are an asshole, it is written all over my face.

If you had to choose only 3 adjectives to describe yourself, which would you choose?  Wild, unpredictable with a tons of joie de vivre!


What do you give a damn about?  Rescuing dogs.

What is a dream you have that you’ve yet to achieve?  To see my book in print.

What’s something you say you’ll do, but never will?  **edited for legal reasons**

What did you have to give up to achieve your current level of success?  My health. 

Has anything ever happened to you that you could not, and cannot, explain?  Yes.  God spoke to me.

Do you ever find there are things about you that people misunderstand? What are they?  LOL totally.  I laugh at the reaction to my other blog.  Lighten up and go get laid.

For what are you most grateful today?  My life.

If you could have one ‘do over’ in your life, what would you do differently?  Get a law degree.

Of what are you most afraid?  The apocalypse or a meltdown at Pickering B.