The Road to Hell Game by
(149 Stories)

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My former wife’s father was a lovely guy; a true mensch.  Even his nickname within the family said as much: “Gentle.”  Though, on those occasions when he did something boneheaded, we did refer to him as “Gentle the Mental.” This story about a game he invented is one such example.

We concluded that it was a really dangerous game to play - a "Road to Hell is Paved With Good Intentions" game...

We frequently went on family vacations — my wife and I and our two young daughters, her parents (Mental and Mrs. Mental), her older brother and younger sister (sometimes with respective significant other(s)), and occasionally my mother would join in.  Really fun, albeit with the usual frictions; no one felt this was driven by dutiful familial obligations.

On one of these vacations, at a dinner near the end, Gentle was in a particularly expansive and sentimental mood.  Out of nowhere, he proposed a game for the table.  The gist of it was that we would all tell another person at the table what we felt was that person’s best characteristic. I was a bit skeptical, albeit for the wrong reasons.  To me, a fairly competitive sort, this wasn’t much of a real game. How did you judge who was a winner or loser; how did you even try to win?  I viewed it as a nice gesture of family love, which was fine in and of itself, but not a game.  But I kept my mouth shut.  I didn’t want to rain on Gentle’s parade.

I forget whether we put names in a hat or just went around the table to decide who would speak in praise of whom. But very early on, it was Gentle’s turn to speak about his younger daughter — who, for purposes of semi-anonymity and presaging, I will call Snowflake.  I should also mention that Snowflake was ten years younger than we were — so probably in her mid-20’s at the time — and at the time very sensitive about her weight and physical appearance generally (though she was really very pretty). So, Gentle, with the best of intentions, thinks for a while and then proclaims that the thing he most loves about Snowflake is her sense of humor.  Well, Snowflake does have a great sense of humor, but this was absolutely the wrong answer.  She paused for a moment, then burst into hysterical tears, wailed at her father “Don’t you think I’m pretty?!” and stormed out of the dining room.

That obviously ended Gentle’s game right there and we all finished the meal in uncomfortable small talk. Obviously, fences were mended — but I don’t think until the next day.   In dissecting the game that night, my wife and I concluded that its biggest flaw was the rule that you had to think of the person’s “best” characteristic.  That really put the pressure on.  But, on further reflection, we realized that that rule would be fairly implicit anyway.  I mean, even if you could list any good characteristic, it’s doubtful that you would first mention, say, being very good at crossword puzzles or parallel parking.  So we ultimately concluded that it was just a really, really dangerous game to play  — a “Road to Hell is Paved With Good Intentions” game — and that one and only time we did play it went down in family lore, especially when we fondly recounted Gentle the Mental Moments.

Amusingly, I sometimes think of the “Road to Hell” game when I am reading and commenting on Retro stories.  As we all know, the Comments section begins, “Say one positive thing about this story.”  I realize that it does not ask us to say the most positive thing, but I still worry a little.  What if I comment that I thought a story created terrific dynamic tension in reaching its climax and the writer feels that I have totally missed the great personal struggle and self-sacrifice that he/she experienced?

So far, so good, but I trust that, if I ever commit such a faux pas, the writer will (gently, of course) set me straight.



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  1. Suzy says:

    John, this is a great story. At first I thought your father-in-law was actually suggesting a game called The Road to Hell – which would have been pretty funny – but then it turned out it was just his good intentions that led there. I have played a variant of this game at a family reunion, but it wasn’t just naming the person’s “best” characteristic, it was saying everything you liked about him/her. So it wasn’t fraught with “oh, you like this about me better than that? how dare you!”

    Ironically, in the current climate, if a man said that a woman’s best characteristic was that she was pretty, people would be outraged. I wonder what Snowflake would think about it now.

    And don’t worry about your comments here. The only sin on Retrospect is not to comment at all. (Although if you should commit a comment faux pas on one of my stories, I would definitely let you know 🙂 )

    • John Shutkin says:

      You’re absolutely right, Suzy; today comments about one’s appearance would be fairly offensive — including to Snowflake, who is quite liberated. And personally, I’ve always preferred that people compliment me on my sense of humor than my rugged good looks.

      And I have no doubt that yuo would let me know — in the nicest possible way, of course — if I committed a faux pas.

  2. Love this story, John, and your writing, and a man nicknamed “Gentle,” whose last name is Mental (really?) and who’s a mensch. What a wonderful character for an entire novel! But am I the only one who thought this was going in another direction? I figured the reason someone would suggest telling each other their favorite thing about them was so that in the next round they could then share their least favorite thing, a “well-intentioned” (read sneaky) way to tell someone something that’s really bugging you but “all in good fun,” and with witnesses and moral support. Clearly there’s more than one Road to Hell…this one could actually be fairly well travelled. I think I’ve even dreamt of taking it with a friend or two but thankfully woke up before I did.

    • John Shutkin says:

      Thanks, Barbara. Gentle’s last name did not, in fact, rhyme with “gentle” — though, come to think of it, it rhymed with “utter.” Your game would be a lot more fun, at least if anyone were prepared for it. Actually, I think they already have that game; it’s called a “roast.”

  3. John, I also had to laugh out loud (again) about the characteristics of “being very good at crossword puzzles or parallel parking” seeming unlikely of first mention. Imagining you coming up with those two among so many possibilities…did you think long and hard or did those just immediately spring to mind? I’d love to hear about other contenders you might have considered.

    • John Shutkin says:

      Thanks, Barbara. I’m afraid I have no idea how my brain works. I first came up with the parallel parking example, but then felt it should be augmented with another example. So crossword puzzles came into the picture. In retrospect (appropriately), I probably came up with those two because they are both things that I am quite good at and yet which I hardly consider my greatest virtues. I’ll have to discuss this further with Dr. Freud at my next session.

  4. Hahaha, John…I’m quite good at both as well and think I’d totally crack up if someone mentioned either as one of my strongest suits. In fact I’m cracking up thinking about it.

    And “in retrospect (appropriately)”…okay, enough already, you made my day.

  5. Laurie Levy says:

    This is a great story, John, because no one wins games like these. We all secretly wish people would recognize what we think is our best characteristic, if we even know what that is. Gentle definitely had good intentions, and was probably shocked that Snowflake didn’t value her sense of humor above all of her other traits.

  6. A thought provoking story, John. Yes, the Road to Hell game is among those that shouldn’t be undertaken, but I think versions of it get imposed upon us, e.g., when someone near and dear asks a question of “what do you think of my . . . ” One hopes that context provides a suggested answer.
    A few years back I participated in a storytelling workshop and on the last day, after we had been together for several days, the instructor told us to think of one quality that another in the group had that we would like for ourselves. Perhaps a much better “game”

    • John Shutkin says:

      Thanks, Tom. And, yes, yours is a much better game. In fact, a lot of the comments to my story have reminded me of much better games. But I am stuck with the one that Gentle proposed, at least on Retro. Though I now see the advantages to being a novelist.

      And even I have never been stupid enough to answer the “Does this make me look fat?” question wrong.

  7. Betsy Pfau says:

    Ah John, these days, even the name “Snowflake” has a different connotation. But what a game your father-in-law concocted; certainly a no-win situation. The “leave one nice comment” came from a writer’s workshop I took on Martha’s Vineyard many years ago and shared that with Patti and John. We met every morning for a week, and were given impromptu writing assignments of varying lengths, went off and wrote, then had to read our stories around the circle and everyone had to make one NICE comment about the story. The writing workshop wasn’t about critique. It was called “Finding Your Voice” because the leader was convinced that somewhere along the way, everyone had been shut down by a teacher or parent or some role model in their lives and this workshop was a safe place to just experiment and open up and learn again to write…anything! Nothing was out of bounds and we could get things off our chests and open up. Some were better writers than others, but there was no critique of style and everyone was valued. It became a form of therapy and really transformative. I took the workshop three times, including the summer after my mother died. So that’s where the “one nice comment” thing came from.

    • John Shutkin says:

      Thanks a really helpful explanation of the “one nice comment” request. And it absolutely makes good sense, particularly in terms of overcoming past efforts to silence one’s voice. (I think I only faced that when I used to blab too much in class in elementary school — not that it ever deterred me.) This was a really nice comment!!

  8. Marian says:

    This game told more about the person giving the compliment than the one who was complimented. My heart aches for Snowflake in the context of the time. We all have experienced “damning with faint praise,” which was a favorite tactic of my mother’s. All that said, one of my old boyfriends, who has a great sense of humor, wants to put “He wasn’t a good bowler” as his epitaph. He really wasn’t a good bowler!

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