So The Mysterious Man is revealed as the Baker's father, which also makes him Rapunzel's father, since she was revealed to be the Baker's sister in the act one opening part 4. Therefore, Rapunzel's Prince is the Mysterious Man's son-in-law. We look now to the part in scene 2 where Jack meets the Mysterious Man in the woods and he tells Jack that he'd be lucky to exchange Milky White for a sack of beans. In this scene, the Mysterious Man refers to Jack by name, to which Jack responds: "How do you know my name?" In the act one opening part 5 Jack's mother said to Jack "Your father's not back." We have decided that the Mysterious Man is secretly Jack's father, and Jack is a bastard. (I would like to take this moment to point out that this idea also came about since in our production these two characters were played by twins, so we were trying to explain their resemblance, which is what started this theory.) Moving on to Little Red Riding Hood; She speaks often of her mother, but never of her father. (also note: her mother is never shown, but her granny is, and in my production Granny looks nothing like Little Red.) If you have ever seen the original cast Open Air Theater version of Hello Little Girl, the way she responds to the wolf just screams daddy issues, more specifically the lack there of, which would have removed any image from her mind about how men were supposed to act around ladies at that time. Her mother seems very protective over her, telling her to never step off of the path and such, similarly to how the Baker says to Cinderella in act two opening part 4: "Our child was very difficult to come by. His safety is of great importance to me." This could mean that Little Red was hard for her mother to come by, one possible explanation was that her mother was never in that sort of relationship or was infertile or something of that sort of nature, and Little Red was adopted (aided by our casting of her only seen relative looking nothing like her, as I said before.) We believe that she is not only another child of the Mysterious Man, but also Jack's twin sister, separated at birth. Jack is very attached to his pets, and a common sign of a child being separated from their twin without knowing it is the feeling that you need someone there with you, but you can't put your finger on who. So Jack tries to fill this gap with his pets. We also decided that Little Red Riding Hood's name is Jill. Not because there is any evidence for that or anything, but if we're doing fan theories about fay tales, why not Jack and Jill*. We believe that one of the children would have been put up for adoption since Jack's family is so poor, they could probably not afford two children and could have used the money from selling their daughter (If any of you watch Once Upon a Time, this is similar to when Prince Charming's twin brother was sold to the king, only not to a king). We also decided that the Mysterious Man is the father of Florinda and Lucinda, because if he's been making his way around the kingdom, it can easily be presumed that he is the father of these fatherless girls as well. We decided that at the beginning of the show, the stepsisters are in their mid to late twenties, the Baker is in his early to mid twenties, Jack and Little Red/Jill are 18, and Rapunzel is 17. Florinda and Lucinda were not from an affair, but instead bastards, and when their mother discovered that her lover was poor she cast him aside and went off in search of a rich man. Since Jack and Little Red/Jill are between the two children The Mysterious Man had with his wife, they would have to be from an affair.
Below is a list of relationships throughout the musical.
Mysterious Man-father/children-Florinda, Lucinda, Baker, Jack, Little Red Riding Hood, Rapunzel
Mysterious Man-father in law/son in law-Rapunzel's Prince
Mysterious Man-father in law/daughter in law-Baker's Wife
Mysterious Man-lover/lover-Cinderella's Stepmother, Jack's Mother
Mysterious Man-grandfather/grandchild-Baker's son, Rapunzel's twins
Baker-half brother/half brother-Jack
Baker-half brother/half sister-Florinda, Lucinda, Little Red Riding Hood
Baker-brother in law/brother in law-Rapunzel's Prince
Baker-husband/wife-Baker's Wife
Jack-twin brother/twin sister-Little Red Riding Hood
Jack-half brother/half sister-Florinda, Lucinda
Jack-half brother in law/half brother in law-Rapunzel's Prince
Rapunzel's Prince-half brother in law/half sister in law-Florinda, Lucinda, Little Red Riding hood
Little Red Riding Hood-half sister/half sister-Florinda, Lucinda
Little Red Riding Hood-daughter/mother-Jack's Mother
Now it gets a little weird
Cinderella-half step sister/half step siblings-Baker, Little Red Riding Hood, Jack, Rapunzel
Cinderella-half step aunt/half step nephew(s) (and niece(s))-Baker's son and Rapunzel's twins
Cinderella-half step sister in law/half step sister in law-Baker's Wife
Cinderella-sister in law/ brother in law-Rapunzel's Prince (through Cinderella's Prince)
Cinderella-half step sister in law/half step brother in law-Rapunzel's Prince (through Rapunzel)
Cinderella's Prince-half step brother in law/half step siblings in law-Baker, Little Red Riding Hood, Jack, Rapunzel
Cinderella's Prince-half step uncle/half step nephew(s) (and niece(s))-Baker's son and Rapunzel's twins
Cinderella's Prince-brother in law/sister in law-Rapunzel (through Rapunzel's Prince)
Cinderella's Prince-half step brother in law/half step sister in law-Rapunzel (through Cinderella)
*It was later added by a friend of mine that the part in the rhyme where it says "Jack fell down and broke his crown" is referring to how (in her words) "embarrassingly stupid" Jack is. Also, I am aware that Jack and Jill isn't a Brother's Grimm fairy tale, but Ben thought it was a cute little addition.
I think that's it, but feel free to let me know if I missed anything, and I'd love to hear your thoughts on this whole thing.