100 questions to spark conversation & connection at the Thanksgiving table.


“A real conversation always contains an invitation. You are inviting another person to reveal herself or himself to you, to tell you who they are or what they want.” –David Whyte


This Thanksgiving? Let’s have real conversations.

Here are 100+ questions to ask your friends, family and dinner companions.

Questions to spark stories, draw out a few secrets, trigger a few belly laughs… and hopefully, help you to feel more deeply connected to the people you love.

Who knows?

With the right question, you might discover something you never knew, about someone you’ve known… practically forever.


. . .


Are there any household chores you secretly enjoy? Which ones — and why?

Are there any laws or social rules that completely baffle you?

Are you a starter or a finisher?

Are you afraid of flying in airplanes? (How come?)

Are you living your life purpose — or still searching?

Are you useful in a crisis?

Can you tell when someone is lying?

Can you tell when someone is telling the truth?

Do you believe in magic? When have you felt it?

Do you believe that everyone deserves forgiveness?

Do you believe that people deserve to be happy?

Do you ever hunt for answers or omens in dreams?

Do you ever yearn for your life, before Facebook?

Do you have a morning ritual?

Do you have any habits you wish you could erase?

Do you have any irrational fears?

Do you have any personal rituals for the end of the year?

Do you have any physical features that you try to cloak or hide? How come?

Do you like to be saved — or do the saving?

Do you secretly miss Polaroid cameras?

Do you think everyone has the capacity to be a leader?

Do you think we should live like we’re dying?

Do you think we’re designed for monogamy? (Why or why not?)

Do you think you’re currently operating at 100% capacity?

Ever fantasize about being in a rock band? What would your group be called?

Has a teacher ever changed your life? How so?

Have you ever (actually) kept a New Year’s Resolution?

Have you ever been genuinely afraid for your physical safety?

Have you ever dreamed about starting a business? (Or if you’ve already got one — a new business?)

Have you ever fantasized about changing your first name? To what?

Have you ever fantasized about writing an advice column? What’s the first question you’d like to answer?

Have you ever had a psychic reading? Did you believe it? Was it accurate?

Have you ever had to make a public apology? (How come?)

Have you ever met one of your heroes?

Have you ever met someone who was genuinely evil?

Have you ever pushed your body further than you dreamed possible?

Have you ever screamed at someone? (How come?)

Have you ever set two friends up on a date? (How did it go?)

Have you ever stolen anything? (Money, candy, hearts, time?)

Have you ever unplugged from the Internet for more than a week?

Have you ever won an award? What was it for?

How do you engage with panhandlers on the street?

How do you reign in self-critical voices?

How long can you go without checking your emails or texts?

How would you fix the economy?

If a mysterious benefactor wrote you a check for $5,000 and said, “Help me solve a problem — any problem!” … what would you do with him or her?

If social media didn’t exist, how would your life be different?

If you could choose your own life obstacles, would you keep the ones you have?

If you could custom blend a perfume or cologne, what would it include?

If you could enroll in a PhD program, with your tuition paid in full by a mysterious benefactor, what would you study — and why?

If you could have tea with one fictional character, who would it be?

If you could master any instrument on earth, what would it be?

If you could save one endangered species from extinction, which would you choose?

If you could sit down with your 15-year old self, what would you tell him or her?

If you had an extra $100 to spend on yourself every week, what would you do?

If you were heading out on a road trip right this minute, what would you pack?

If you were searching through an online dating website, what’s the #1 quality / trait that would attract you to someone’s profile?

If you were to die three hours from now, what would you regret most?

If you wrote romance novels or erotic fiction, what would your “pen name” be?

Is there something that people consistently ask for help with? What is it?

Is war a necessary evil?

What are you an expert on? Is it because of training, lived experience, or both?

What are you bored of?

What are you devoted to creating, in the New Year?

What are you freakishly good at?

What are you starving for?

What do you value most: free time, recognition, or money?

What is your spirit animal?

What was the best kiss of your entire life?

What was the best part of your day, so far?

What was the most agonizing hour of your life?

What was your proudest moment from the past twelve months?

What was your very first job?

What was your worst haircut / hairstyle of all time?

What’s going to be carved on your (hypothetical) tombstone?

What’s in your fridge, right this moment?

What’s in your pocket (or purse, or man-purse) right now?

What’s one dream that you’ve tucked away, for the moment? How come?

What’s one mistake you keep repeating (and repeating)?

What’s one thing you’re deeply proud of — but would never put on your résumé?

What’s something you’ve tried, that you’ll never, ever try again?

What’s the best birthday cake you ever ate?

What’s the best compliment you’ve ever received?

What’s the hardest thing you ever had to write — and why?

What’s the last book that you couldn’t put down?

What’s the most out-of-character choice you’ve ever made?

What’s the strangest date you’ve ever been on?

What’s the title of your future memoir?

What’s the worst piece of advice you’ve ever been given?

What’s your definition of an ideal houseguest?

What’s your guiltiest of guilty pleasures?

What’s your most urgent priority for the rest of the year?

What’s your personal anthem or theme song?

What’s your recipe for recuperating from extreme heartbreak?

When was the last time you astonished yourself?

When was the last time you got stuck in a rut? How did you get out of it?

When was the last time you saw an animal in the wild?

When you see peers / competitors getting things you want, how do you react?

Where & when do you get your best ideas?

Who is the last person that deeply disappointed you? (What happened?)

Would you consider yourself an introvert, extrovert, or ambivert?

Would you like to write a book? (About what?)

Would you rather be a lonely genius, or a sociable idiot?

Would you rather have a live-in massage therapist, or a live-in chef?

Would you rather have an extra $200 a day, or an extra 2 hours a day?

And of course…

What are you most grateful for, right now, in this moment?


. . .


Sending big love from my home, to yours.

I hope your holiday table is full of laughter, good food, and surprising revelations.

To the art of conversation…



Read More creativity // inspiration devotion // liberty

Email subject lines that I would love to see in my inbox.


SUBJECT: This is the shortest email you will ever read.

SUBJECT: Except for this one. Which is shorter.

SUBJECT: You are pretty and smart. No response required.

SUBJECT: Hey Alex! It’s me, Mister Rogers! Just kidding! I’ve been alive this whole time!

SUBJECT: Hey Alex! It’s me, Oscar Wilde! Me, too!

SUBJECT: Hey Alex! It’s me, God! You were right. I’m totally real.

SUBJECT: Greetings from RuPaul! Brunch? This Sunday? You, me, Fred and Oscar?

SUBJECT: Hey Alex! I had a question for you, but then I Googled it instead. No response required.

SUBJECT: Hey Alex! I had another question for you, but then I trusted my own intuition instead. No response required.

SUBJECT: Hey Alex! My intuition was totally right. As usual. No response required.

SUBJECT: Dear sir / madame. Your penis is exactly the right size. Carry on!

SUBJECT: I would like to unsubscribe from your mailing list but I’m going to be super nice about it and totally not yell at you in ALL CAPS.

SUBJECT: I am a robot and I did all your laundry. You may rest now. No response required.

SUBJECT: Open me for baby otters and also pandas.

SUBJECT: Alex, this is Bill Clinton. I’ve been thinking about that letter you wrote to me when you were 10. About the sharks. You were totally right. They are intelligent creatures and they deserve cleaner oceans and far more respect. XOXO. BC.

SUBJECT: INSTANT ORGASM FOREVER!!! Details = inside. (30% off. Black Friday Sale.)

SUBJECT: This email literally has five words.

SUBJECT: This email literally has three words.

SUBJECT: This email is literally just a photo of a baby duckling.

SUBJECT: Alex: This is your official reminder to take a break from answering emails & go write a book or something. Love, The Universe.


PS. Your fantasy email subject line. GO.


Read More Uncategorized

GOOD QUESTION: How can I create a clear “brand” and “message” when I love to do so many different things?


Dear Alex,

I’m feeling lost.

I’ve poured years of my life into building a business that (I thought) would be a success.

I’m doing fine, but not as “fine” as I’d like.

It feels like squeezing water out of a stone every time I launch a product. I pour my heart and soul into the process, but nobody bites. I literally had ZERO sign ups after my last product announcement. Not fun.

After some reflection, I think I’ve diagnosed the problem. I’m trying to be and do too many things, at once. My message is scattered. My offerings are all over the place. I don’t even have a clear “job title”. No wonder people aren’t buying.

I know that I need to make some changes, but I’m not sure where to begin.

My question for you is:

How can I create a clear “brand” and “message”, when I love to do so many different things?

–[Please Don’t Use My Name]


Dear Lovely Anonymous Person,

I have a strong opinion about your conundrum. And my opinion may be… an unpopular one.

You asked:

How can I create a clear “brand” and “message”, when I love to do so many different things?

My answer is:

You can’t.

Clarity — by its very definition — requires sharpness, crispness and distillation. It requires subtraction, not addition.

If you want to have a clear brand and message — one that people can immediately grasp & get excited about — then you have to make some tough choices.

You have to commit to a particular path, and keep marching. You have to focus your energy. You have to do less and do it better.

In the historic speech that transformed our world forever, Dr. Martin Luther King Jr. cries out, “I have a dream…” not “I have LOTS of dreams and let me tell you about ALL of them, right now!”

To communicate powerfully — and resonate deeply — you must exercise some constraint.

But… exercising constraint doesn’t mean that you are trapped in a tight little box for the rest of your life.

Picasso had his Blue Period, then his Rose Period, then his Cubism Period.

You can evolve through several iterations of your work, too.

But whatever period you’re in, right now? Be fully in that period.

Choose a dream. Choose a topic. Choose a job title. Choose a message. Commit.


“You rarely have time for everything you want in this life, so you need to make choices. And hopefully your choices can come from a deep sense of who you are.” ―Fred Rogers


“One is not born into the world to do everything, but to do something.” –Henry David Thoreau


“Creativity is subtraction.” –Austin Kleon


“Concentrate all your thoughts upon the work at hand. The sun’s rays do not burn until brought to a focus.” –Alexander Graham Bell


“You can have it all. Just not all at once.” ―Oprah Winfrey


Constraint is not a cage.

Ironically, it is the opposite.

Constraint is the choice… that will set your best work free.



PS. Fill in the blanks:

Right now, through my work, I am trying to ______________________.

That is my focal point. That is my cause. That is the primary miracle that I am trying to create.

And that is why, right now, my primary message is ______________________.

My message might change, in the future. But for now? THAT is IT.


Read More good question

Teach people how to treat you. How to write clear, loving policies for your business & life.


You teach people how to treat you.

You teach people how to communicate with you.

You can’t expect people to “guess” your policies, expectations, hopes and dreams.

You have to share them. Clearly.

You also have to enforce them. Consistently.

Otherwise, people won’t know what you want. They won’t know how to play with you. They will (probably) disappoint or frustrate you, and it won’t really be their “fault”.

This is a lesson that I have learned slowly… and with great difficulty. (I owe a great debt to Dr. Suzanne Gelb, a psychologist who has dramatically changed the way that I think about “enforcing boundaries and policies”. Her guidebooks, by the way, are true gems.)

In a few weeks, on my thirtieth birthday, I will be launching a brand new website, complete with new language, new offerings… and crystal-clear policies.

I feel nervous, but mostly excited. (Nervcited.)

I’d like to share a few of my new policies with you, today, along with my thoughts on how to craft clear, loving policies of your own.

Here we go…




In 2015, here is what you should know about working & playing with me:


My re-publishing policy.

If you see something on my website that resonates with you — an idea, a quote, a script — feel free to re-publish it on your own site, in your magazine, in your book, or anywhere else that you like.

You don’t have to reach out to me for permission. Just go for it!

All I ask is that you mention my name & link back to my website: AlexandraFranzen.com.


My advice policy.

I love sharing what I know & offering helpful advice as often as I can — but I do not give “free advice” via email.

Instead, I have an advice column. It’s called Good Question.

If you have a question that you’d like to see me answer in a future column, please send it to me.

I can’t answer every question that I receive, but if I choose to answer yours, I will send you a personal note to let you know.


My “tough love” cancellation policy.

If you are purchasing a ticket to one of my events, please know that your ticket is “non-refundable and transferrable.”

This is a fancy way of saying:

If your plans change, and you are no longer able to attend the event, you cannot “cancel” and then get a refund.

What you can do is: 1. Switch into a different event, if I have space. 2. Give your ticket to somebody else. 3. Sell your ticket to somebody else. It is your responsibility to find that “somebody else”.

I have been quite lenient on this policy in the past. No longer. This is firm. Tough love.

Bottom line: Just come. Don’t flake out. Be brave & show up. It’s good for the soul.


Thank you for reading my policies.

I enjoyed writing them, and I will enjoy enforcing them… with love.




1. Start with this question: “What is making me feel resentful?”

Resentment is a sensation that signals: “Something has got to change.”

Are clients constantly cancelling at the last moment? Are students flaking out on your workshops? Are people pestering you with an unnecessary amount of emails? Or sending messages that are long-winded and confusing?

Identify the moments in your day, week or month that trigger feelings of resentment. Those are the places where you’ll want to write some new policies.


2. Your next question is: “What are the questions that I get asked, repeatedly?”

Are people constantly emailing you, seeking free advice? Or asking for discounted rates? Or donations? Or asking you to do things that you don’t want to do?

If you’re feeling tired of answering the same questions, over and over, then you have an opportunity to clarify and tighten up your policies — or perhaps, create a set of Frequently Asked Questions — so that people understand how to play with you.


3. After that, ask yourself, “What are the questions that I WISH I was getting asked, repeatedly?”

Do you want more media bookings? Or more opportunities to speak onstage? Wish people were “quoting” you in their books and blog posts? Want people to hire you for a “new” kind of service?

People might not know that you want those kinds of things. You need to teach them.

So, write policies for the things that you want — even if you’re not getting them, yet.

Your words will act like magnets, drawing those kinds of opportunities to you.




Case studies.
Cell phone usage.
Classroom behavior.
Customer service.
Dinner time.
Following up.
Household chores.
Media appearances.
Re-publishing / re-using your work.
Rescheduling appointments.
Shared responsibilities.
Social media.
Working for free.

… for starters.




Resist the urge to “explain” or “justify” your policies.

Just state the facts.

There’s no need to describe the ten years of misery and personal growth that went into establishing those facts.


“In 2015, my rate is $250 an hour.”

Is much more clear & powerful than saying:

“After a great deal of thought and consideration, I have decided to raise my rates — slightly — in order to provide better service while honoring my commitment to self-care. This is why my rate will be going from $200 to $250 an hour. If you have any questions about this change, please let me know. In some instances, I will be willing to honor my old rate for long-time clients, as well as new clients with financial difficulties. I also offer packages of time, which leads to a lower hourly rate when you purchase in advance. [etc…]”

Don’t explain. Don’t waffle. Don’t apologize. Don’t create “exceptions” and “loopholes”. Don’t invite “questions” and “commentary”.

Just say what is true. Clearly. Simply. No additional fluff.

Teach people what to expect from you.

Teach people how to treat you.




PS. Are you changing a personal or business policy in the New Year? What’s the new policy?


Read More business // acceleration

Please ask yourself this question before you choose the “format” for your next product, service, art project, or heart project.


Here it is:

“What is the effect that I want to have on people?”

Start there.

Or, to frame the question differently:

“What kind of impact do I want to have?”

“What kind of experience do I want to create?”

“How do I want people to feel?”


If you want to create an experience of connection, intimacy, closeness, tribal communion…

Is an e-course with hundreds of participants and zero face-to-face contact really going to create that kind of effect?

Maybe a private, invitation-only salon in your home, with twelve people, is a much better choice.


If you want people to feel energized, lit up, clear, ready to take action NOW…

Is a 5,000 word essay, full of charming stories and tumbling side-rambles, really going to inspire that kind of feeling?

Maybe a brief, heartfelt, three-line manifesto, with tremendous economy of language, is a much better choice.


There are no “good” formats or “bad” formats.

There is only the optimal format for the specific experience that you want to create.

What is the experience that you want to create, for your audience? (Your audience of one… or one thousand… or more?)

Decide that, first.

The right format will be obvious and clear, once you know.