nimblesnotebook:

For those who don’t know, a Sweet Polly Oliver is a female character who dress up as and takes the role of a man for whatever reason and Sweet on Polly Oliver is when a male character becomes attracted to this character, which often causes a lot of internal conflict. Examples are Mulan and She’s the Man/Twelfth Night.

Sweet Polly Oliver:

• Your character be believable. What makes your character perceived as male varies by time period and culture. In some places it might be as simple as changing clothes. In others more elaborate measures will be needed. Either way, you have to make sure your character won’t raise suspicions on sight. This also means that your character should enter the world of a new gender with some difficulty. She won’t be used to the social behaviors and she may start noticing extremely subtle gender roles.
• Your character needs a reason. Female characters dress up as male characters for a reason. Furthermore, dressing as a guy needs to be related to their reason. It can’t just be “I need a disguise of any kind and therefore will choose to be male”. It should be “in order to achieve X, I must be male”. A cliche would be women dressing as men to become warriors/knights or to go to war, but you can still make it more original by playing with motive and situation (even just changing the time period to, for an American example, the Civil War can change it up from the common medieval setting).
• The Name: It’s easier for people to change their name to the masculine version because they’ll most likely respond to it, but try to do something else. “Samantha” to “Samuel”, “Gabriela” to “Gabriel”, “Colleen” to “Collin”…while convenient it’s a bit cheesy and it has the potential to give away you character’s identity depending on the situation.
• What it is Not: Because I feel like I need to clarify this, this trope does not include: masculine women being mistaken for men, female characters dressing up as men for entertainment, and trans men.

Sweet On Polly Oliver

The main problem I have with this trope is how the characters confront their sexuality. Men who are attracted to the woman-in-disguise often try to reassert their heterosexuality while women who are attracted to them woman-in-disguise are disgusted when they find out they actually had a crush on another woman.

In addition, you should have reasons for why this character is attracted to the female character in disguise, just like you would have reasons for why they would like any other character. Try to avoid the “there’s just something about him” narrative as if your character can just “see right through the disguise”.