Do a Best Day and Worst Day For Your Characters

by James Scott Bell

Back when I was first learning how to write fiction, I concentrated on plot and structure. These were the parts of the craft that were most mysterious to me. I had no idea how the writers I enjoyed came up with twisting, turning plots that held delightful surprises and satisfying endings. I thought they just sat down and started typing, and therefore had an inner genius I lacked. I’d been told as much in college: “You don’t have any inner genius, Mr. Bell.” Okay, maybe not in those exact words, but it was implied. I was certainly told I couldn’t learn how to write great fiction. You either have it or you don’t, they said.

I apparently didn’t have it. So I went into a much more stable profession—acting. Then I got married (see last week’s post) and decided a steady income was actually a good thing, so I went to law school.

Some years later I saw Moonstruck and had to find out if I could, after all, learn to write.

It took me a year of study to get a handle on structure. During that year I was concentrating on screenwriting. My primary text was Syd Field’s Screenplay. I still remember the joy I felt when I finally started to see what was going on structurally, and then added to the mix my formulation of the “doorways of no return.”

So I wrote a screenplay (my fourth or fifth effort) based on what I learned. An up-and-coming Hollywood agent consented to read it.

I sent it to her.

And vividly remember the phone call. She told me the plot was good, but the script didn’t do it for her, because “the characters don’t jump off the page.”

After retrieving my heart from my shoes, I sat back and thought about her comment. Intuitively, I understood. After all, the movie that re-awakened my desire to write, Moonstruck, is full of characters who “jump off” the screen. Even the minor ones.

That’s what was missing in my screenplays.

So began another course of study to figure out characterization.

As usual, I got some craft books and re-read a few favorite novels with great characters. I studied and practiced and, lo and behold, landed a book contract. After a few years I began teaching workshops and writing my own books on the craft.

Here’s the new one: Writing Unforgettable Characters: How to Create Story People Who Jump Off the Page. (See below for pre-order info).

I’ve included a number of my workshop exercises in the book. One of my favorites is “Best Day, Worst Day.” I got this idea from the hit comedy City Slickers. Remember? Billy Crystal, Daniel Stern and Bruno Kirby play three friends: Mitch, Phil and Ed. They are almost 40 years old and have come to a point where they look at their lives and think, Is this is as good as it’s ever going to get? Mitch is stuck in a job he hates. Phil is stuck in a terrible marriage. And Ed is stuck in a macho image hiding his insecurities.

So the three decide to get away from it all and go out West for a “real” cattle drive. They join with a few other tourists. And then meet the tough trail boss, Curly (Jack Palance, in an Oscar-winning turn).

The superb script (by Lowell Ganz and Babaloo Mandel) is an example of what I call “orchestration.” You cast your characters so they are different enough from each other that conflict can naturally occur. This is especially important for your allies (characters on the same team).

At one point the three friends are riding along, and Mitch tells about the best day of his life (his father taking him to Yankee Stadium for the first time) and his worst day (the day a lump was found in his wife’s breast). Then:

Phil: All right, I got one. My best day—

Ed: This isn’t the one about Arlene and that loose step, is it?

Phil: No, my wedding day.

Mitch: What!

Phil: Yeah, remember that day? Outdoor wedding. Arlene looked great. Those water pills really worked. You guys were all smiling at me, and my dad, in the front, gives me a little wink, you know? I mean, he’s not the warmest of men, but he winked. I was the first one of us to get married and have a real job and I remember thinking, I’m grown up, you know? I’m not a goofball anymore. I made it. I felt like a man. That was the best day of my life.

Ed: What was your worst day?

Phil: Every day since is a tie.

Then the question is asked of Ed, who at first refuses to answer. But then:

Ed: I’m fourteen and my mother and father are fighting again, you know, because she caught him again. Caught him! This time the girl drove by the house to pick him up. And I finally realized, he wasn’t just cheating on my mother, he was cheating us. So I told him, I said, “You’re bad to us. We don’t love you. I’ll take care of my mother and my sister. We don’t need you anymore.” And he made like he was gonna hit me, but I didn’t budge. And he turned around and he left. Never bothered us again. But I took care of my mother and my sister from that day on. That’s my best day.

Phil: What was your worst day?

Ed: Same day.

That is just flat-out great dialogue. But for our purposes, it is also a fantastic exercise for deepening your characters before you render them on the page. The nice thing is you don’t have to put the material in your novel (though you certainly may). Just knowing it for yourself will automatically give you a better, more complex character. So brainstorm away, be ye plotter or pantser. You’ll be glad you did.

You’ll find more exercises like this in Writing Unforgettable Characters, which you can pre-order here:




A print version will be also be available soon.

Why don’t we play half this game today in the comments? What was one of your best days or favorite memories?

41 thoughts on “Do a Best Day and Worst Day For Your Characters

  1. Great post, Jim. I look forward to buying your book when it comes out in print.

    I noticed this morning that no one had yet left a response to your “best day” question. I played chicken and went off to check my email before coming back. Still no responses.

    The best day of our life, by definition, would have been filled with emotion. Is that why it was the best day of our life? And, are we a little reluctant to share some of that emotion about ourselves?

    So, I’ll jump first. (But do it with a bungee cord.) The best day of my life was the day I met my wife. I was emotional enough about your post last week that I made my Cindy read your post. She loved it.

    And, without the emotion, I met my wife at a conference. We ended up seated beside each other. We struck up a conversation. And by the end of the conference I was smitten. (And I’ll omit the rest of the emotion.)

    So, thanks for a great post, and have a wonderfully emotional day.

    • Thanks for jumping in, Steve, and for that memory.

      Maybe today’s question is a bit too personal…I’m going to edit the question to “one of your” best days. Maybe that’ll encourage more participation.

  2. Can’t to get my grubby little hands on your new book!

    For a purely earthly best day: Each of the three days I held my three children for the first time. Really can’t beat that.

    Running a close second? The day in 2016 I sold out of all the books I brought to a book signing event. Not talking hundreds, but enough for me to realize maybe, just maybe, I might be able to do this. 🙂

  3. Hi, Jim

    I love this exercise. It’s a great way of uncovering not only important moments in characters’ lives, but how they think, feel, and remember. (And that is a fantastic dialogue exchange in City Slickers.)

    I’ve been blessed to have many best days in my life, far more than the other kind. The day I met my wife (which I mentioned in my comment last week to your wonderful post), and the day we married. The most recent “best day” was the day I retired from the library, last December 20th, after working there for over thirty two years. I gotten hired at the library fresh out of college, planning on working there for just a few years, until I “made it” as a fiction writer and could go write full-time. It didn’t work out l

  4. One of my happiest days was the day I was offered a three-book deal from my dream publisher. I’d been working half my life and in particular the last three years for this contract. It was surreal, looking back even now.

    • Patricia, you brought back to me the day I got offered my first multi-book contract. The editor called me and asked if I’d be interested in a five-book deal, with a healthy advance. All coolness left me. I started sounding like Jackie Gleason on The Honeymooners when he just babbles, “Habba habba habba…”

  5. like I’d planned. Instead, I made a career out of it. I learned about life, about people from all parts of the world, all faiths, many languages, ethnicities and so on, young and old. I learned to teach classes. I learned to tell stories to children.

    The day of my retirement was the best day because it was the culmination of all that. Two retired managers of mine returned to celebrate with you, coworkers present and past. Several patrons, friends and family. It showed me how much the library had shaped me and made me what I am today. I’ve eternally grateful for the opportunity, summed up in that last day. That’s why that last day is one of my best days.

    I’ve pre-ordered your book and am very much looking forward to it.

    (Apologies for the post being split in two–WordPress seemed to hiccup on my end, probably pressed a wrong keyboard combo.)

  6. Hmm, tough question. Most of my days I consider good days. Can’t say one of the best was my wedding day. Though for us it was a great day, the JP showed up drunk and fell off the stage at the end of the ceremony. Holding my first grandchild was definitely one of the best days. But I think I’ll have to go with last Christmas. It was such a special day for many reasons. I hadn’t seen my brother in 20 years, and he came and stayed late into the night. We rekindled our relationship that day. And my sister, who I never knew existed till last year, also attended with my new brother-in-law. For the first time in forever I had guests on my side of the family.

    • Wow, that is a special day, Sue. I love family reconciliation stories.

      I must say, however, that the JP falling drunk off the stage would make a great scene!

  7. Jim, good question but also tough to answer.

    So many “one of the best days” in my life. Hard to choose. At the same time, so many “worst days” also come to mind. Like Ed in the example, often they are the same day. The irony of life.

    Here’s one of the best: When a publisher accepted my book, Instrument of the Devil, of course I told/emailed dozens of friends who knew how many years I’d worked toward that goal. I expected (and of course welcomed) their congratulations and good wishes b/c most were fellow writers who had walked that same road and understood the significance.

    What I didn’t expect was the response from *civilians*–friends and acquaintances who live *normal* lives and don’t write.

    The next day, when I walked into my zumba class at the gym, twenty-five people applauded and cheered. One friend, who’d shared the news with everyone, presented me with a bouquet of flowers. Embarrassing and wonderfully sweet.

    Their response also made me realize the accomplishment of publishing a book had meaning to *regular* people outside the small, isolated world of writing.

    I dislike the overused term “validation” but that’s what it was.

    And it was cool.

  8. My best day…this is a GREAT question & one I want to explore more in my morning pages later. But right now, off the cuff, I have 2 best days, thematic in my life in their own ways:

    1) The day I was born and became the daughter of my father. Unfortunately, my father is no longer alive, but we kids ADORED him & still do. And I feel a special heartbreak for people I talk to (and it happens a lot) who have unfortunately NOT had that experience with their dad (like Ed in City Slickers). The importance of a father figure is a thread that is a very common theme in my fiction.

    2) The day I moved to Arizona: I grew up in Maryland. Flat as far as the eye can see and not what I deem attractive (others may disagree but to each their own). I MUST have mountains. It’s a requirement as basic as breathing. Arizona is the polar opposite of where I grew up–mountains and beauty everywhere and Arizona has such geographic diversity. I may have been raised on the east coast but my soul is the child of the wild west and always will be.

    • You’re a woman after my own heart, BK. I was blessed with a great father and mother. And I love the Southwest. I’m sorry, but I can’t imagine living in Fargo.

  9. One of the problems with getting old is that the good memories smooth out like well-worn river stones under your feet, but most of the bad memories remain sharp enough to stab you through the heart, or, at the very least, painfully prod your bare foot. Days, as a whole, do the same.

    I’ve had wonderful moments/days throughout my life from my education and profession to family and personal successes to days I should have died and didn’t, but one moment stands out strangely although it doesn’t remotely resemble any of the other wonderful moments. After my dad’s death, I became my mom’s and the family homeplace’s caretaker with no education in either. I was a frinking English major on the way to finishing my doctorate for Pete’s sake. The home is surrounded by five acres of lawn, gardens, and woods, and I need a large lawn tractor to hold back the wilderness.

    One day in early summer, the tractor wouldn’t start, and it wasn’t the usual and simple suspects I could fix. The only company who could repair it, warranty work, said they wouldn’t even look at it for three months. I got p*ssed, bought some books on repairing B&S engines, and went to work for days in the miserable heat. Words not suitable for a Southern lady, bloodied hands, dropped tools, bug bites, and a sore back followed, but I persisted. Despite being a “dumb woman” who knew nothing about all things mechanical, I ended up rebuilding the carburetor, and the tractor ran perfectly again. The elation that I did something that was totally out of my experience and expectations of myself was greater than passing every educational milestone I had ever set for myself. I will never forget that moment when the engine turned over and started to purr. It was also the moment I realized I could do almost anything if I put my mind and my stubbornness to it.

    • That is a great day, Marilynn. What an accomplishment. There’s nothing quite like the feeling of determining to learn something, learning it, then seeing it put to practical use.

  10. A favorite memory from a day in my eight-year old life:

    My father was the chief clerk on the Boston waterfront (longshore). I had the day off from school, so he volunteered to bring me to work with him. This was long before “take your daughter to school day,” and many years before any women worked on longshore. First thing, my father brought me aboard a Dutch cargo ship docked in Boston and straight to the commissary, where whoever manned it gave me a bag of Dutch chocolate bars.

    I spent the rest of the day in my father’s big bare office, while he made his rounds supervising the loading & unloading of cargo by union members and scalawags (nonunion members hired as day laborers). There were no secretaries to babysit me, so that task fell to a couple of longshoremen, who did their best to entertain me for four hours. They did magic tricks and let me read the newspaper out loud to them. Then one of the guys showed me how to place blank paper over carbon over the newspaper and trace comic strips. That occupied me until my father returned. I had a wonderful time, but I think the two longshoremen would have preferred unloading cargo.

  11. Great question. I too have many best days. One that stands out is Mother’s Day 2019 when my husband gave me a new digital camera. I took 2000 pictures the first weekend I had it! My daughter rides horses and it was horse show weekend. I had an abundance of interesting subjects to photograph. I took one of my all time favorite pictures of my daughter and her horse that weekend. I love capturing emotive images that stick with me. I now use my images as writing prompts to tell stories. It’s great fun to paint pictures with words.
    If you’re interested in reading my stories I post them on my blog on my website.

    I love your books. I’ve read Plot & Structure 3 times. I look forward to reading your new book.
    Keep up the great work!

    • Thanks for the good word, Lisa. And yeah, I remember when camera phones caught on. Sheesh! Couldn’t stop clicking. The whole world can’t stop clicking.

  12. Great exercise! I can’t wait to try it out for my WIP. Getting the book too.

    Worst – The day my father died when I was 12.
    Best – The day I meet my husband and knew he was the one.

  13. Jigging for cod and haddock with my grandfather (who had a 7th grade education, but could build a house) aboard his Cape Islander in the summers. The smell of diesel, propane, and salt air still makes me wistful. All of my best memories have to do with the ocean.

    MOONSTRUCK is my favorite movie of all time. It’s as close to perfect as I’ve seen – must have watched it dozens of times. Looking forward to reading your book. Memorable characters, IMO, can take a story from good to spectacular.

    • Sue, so often the sense of smell brings back pleasant memories. That’s an important aspect to include in our fiction, too.

      Glad you’re a fan of Moonstruck. I so agree with you.

  14. Great question. I’ve had lots of memorable days, good and bad. However, I’m happy that you decided to focus on the good days. Most of my happiest days revolve around my beloved son. It’s hard to choose just one, but one really nice day for me was when my son, at the age of eight, was selected to be the concertmaster of a high school orchestra. Wow, I was a proud mother that day, because I know how hard he worked to prepare his audition materials. I knew he deserved the honor, but I didn’t know any conductor would have guts enough to make it so. For anyone who is interested, here’s a YouTube video of that particular occasion (

  15. I have two best days:
    1. After a bumpy start to our relationship, I went for a ride in my car with the man who would become my husband, and I realized during that short ride that he was the one.
    2. The day our son was born.

    Most of the days of my life have been wonderful, but none of the others can compare to those two.

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