It goes without saying that every game depends on the group, including party games like charades or board games like Catan. But role playing games can be a lot more easily broken by a group that doesn't mesh well with it.
And, of course, some games are easier to break than others. The fourth edition of Dungeons and Dragons, despite having plenty of detractors, did a good job of being a game that could still work even when people were actively trying to break the system.
(Just for the record, I personally found fourth edition to be a good game but one that didn't feel like D&D to me. Just so you know where I'm coming from)
A Penny for My Thoughts, on the other hand, strikes me as a game that can easily crash and burn with a group that approaches it in the wrong way, even if you don't have any outliers looking to spoil the game.
In A Penny for My Thoughts, the players are amnesiacs who are using a telepathic drug as a form of group therapy to regain their memories. The whole idea behind the telepathic twist is that it lets the other players feed information into the active player's story.
At the start of the game, everyone writes down five memory cues on slips of paper and puts them in a bowl. Everyone then draws a penny (a penny for my thoughts) from a bowl. One person gives their penny to another player and the player with two pennies starts the first memory.
At the start of a memory, the active player draws a cue and everyone else asks them a question about it, creating a framework for the memory to develop.
When the active player reaches an important decision, they will ask two other players what happened next in the memory. The active player MUST choose one of the two options that they are given and gives a penny to the person who offered them that choice.
When they run out of pennies, they've completed the memory. They write it down on a questionnaire that helps guide them, draw a new penny and the role of the active player moves to a new player.
When everyone has completed out their questionnaire, the game ends with everyone making the choice to remember their life or not.
There are two big potential game breakers I see in A Penny for My Thoughts (and, to be fair, the author does address both of them)
The first one is that the baseline game is set in the regular world. No science fiction or fantasy or super hero or spy movie elements. The issues that caused you to lose your memories are likely to be real and potentially painful things like divorce or PTSD or suicide or such.
That can be a really hard sell and people can really pull away from a game that is too grounded in reality. I remember being told about a game of Ribbon Drive where one player redirected the game into being about vampires going to Las Vegas. In ribbon drive is probably one of the most found grounded in reality games I've ever seen, other then some Nordic LARPs that are flat out supposed to be about regular life. Another time in the game of Fasco that I was in, one player had his Steve Busceme style gambler turn into a magical China man who flew off on the back of the golden dragon to Middle Earth. Yes, that's right. I was in a game of fiasco that turned into Toon. (which does have its own weird sense of cool)
Interestingly enough, the author solution is pretty simple and obvious. Change the background setting something more fantastic, like having the characters be secret agents like Jason Bourne or in a Lovecraftian and story. He includes new background material in questionnaires for such games.
I can picture playing the base game with my old Indy group from Chicago. Otherwise, I would skip the base game altogether. Buckle up, this bus is going straight to Cthulhu Country.
The other issue that I see the game having is that somebody else sets up the key decisions for you. The critical decisions that you develop in your memories/story are ones that other people make.
Honestly, this doesn't worry me nearly as much. When you are playing games that are about collaborative storytelling, you're going to have to trust the other players. But I certainly know people who this would be a big problem.
A Penny for My Thoughts uses the props from party games to create a dialogue between the players. At its best, it will create very personal stories in one session. However, I think I would tone it down for everyone's comfort level.