There are a number of romance possibilities, some with full paths and endings and others with brief interactions. Most romantic characters also have a 'friends' relationship available, for players not interested in pursuing the romance.
Main Romance Options in Horse Hall
To romance Damien you must agree to take his hand and be his freshman during initiation, then make up with him on Halloween. Then you will be able to choose him at Christmas. It's possible for Damien to try and date you even if you didn't choose him at Christmas.
To romance Donald you need to make friends with him by going along with his pranks and schemes. You can meet him in detention, or help him out with the "box" prank after the first exam, or defend him after the dueling session. If he likes you, he'll invite you to merit-earning activities with him, and you should be able to choose him at Christmas.
Be nice to Ellen in the first semester and you should be able to choose her at Christmas. To start a romance send her a romantic valentine.
To romance the Professor you have to win the election for class treasurer. Then in the second semester you will run into him performing a ritual. Try to rescue him and the romance path will start.
Be nice to Virginia in the first semester and you should be able to choose her at Christmas. To start a romance you will need a high Weird score.
"Big" Steve Kenyon
The secret romance option, sort of. If you get him to win the bunny from the claw machine and then give it to him you'll get a few scenes with him later. In the later versions of the game (including all Steam versions) you can now go out with Steve and dance with him at the end of the game.
Brief Romance Interactions in Horse Hall
You can't have a relationship with Pastel in Horse Hall but you can get a kiss, if you send her a valentine she pops up later and sprays you with perfume and asks you to kiss her.
Main Romance Options in Wolf Hall
In Magical Diary: Wolf Hall, there are a number of characters that have completely developed romances.
To enable Minnie's route, you must become co-presidents with her. Be aware that you'll need to choose more Flirt Points early on if you intend to take the Distract Damien path.
Spend a lot of time studying with Minnie or helping other students on the weekends. You will want 25 Red Magic before the Dark Dance and 20 Black Magic by just after the 2nd Dungeon Exam for maximum Minnie Points. Another point to remember is on January 10th you MUST choose the "Sad..." option.
Talk to Barbara often by going to the dungeons on Saturdays to enable her route. If you run for President, she will stop talking to you.
You must split up Damien and Ellen in order to pursue Ellen's route. You can choose to distract Damien and then break up with him at the Dark Dance, or you can choose to distract Ellen and confess the truth to her after the Dark Dance. If you distract her and don't confess, she will later dump you for Damien.
When William asks you to distract Ellen from Damien, suggest to distract Damien instead.
When William asks you to distract Ellen from Damien, suggest to distract Damien instead. You have the chance to break up with Damien for William later.
Other May Day Ball Dance Options
There are other people you can dance with at the May Day Ball in Magical Diary: Wolf Hall, though not all of them have fully developed routes.
To access his side route, join the Mushroom Club and make sure Manuel is elected treasurer (which means you cannot become Co-President, and you must vote for him).
To access her side route, follow William's route to Valentines Day, then send him a romantic valentine. Do not confess in private, and he will break things off with you. You can then pursue Angela.
To dance with Laurel, go to the May Day Ball by yourself, and reveal your true identity. She, as the Princess of the May, will dance with you.
To unlock Pastel's side route, follow Minnie's route, and give in to Pastel's blackmail to break things off with her.
[To dance with Luke] December 10: Help Luke Out. December 20: Think of Luke. January 8: $5 Bingo. January 13: Choose "adventure" and sneak into the dungeons. February 10: Buy Luke a $5 Valentine Gift. March 17: Invite Luke to the $5 play. April 1: Choose to participate in his April Fool's Day Event. April 9: Defend Luke or Stay Silent - does not matter which. April 17: He'll try to define the relationship, in which you'll select the option that you didn't know he was interested. Afterwards, you get the chance to ask him to the dance. May 1: Dancing with you. (Hint: You will be given many opportunities to play bingo. It may be best to avoid taking out the candidacy loan, and for bonus "content," you can meet him in detention.)
Go to the May Day Ball by yourself, and DON'T reveal your true identity.
There is an early scene with Raven in the Magic Shop. (Unsure how to get this to pop) Then after the Dark Dance look for Barbara. You'll see Raven in the library if you study the next day (unsure if this matters.) Then on 11/23 go window shopping at the mall for a scene with Raven. If you've gotten enough Raven points you'll be chosen to be Raven's secret Santa.
Talk to her at club signups. Get 15 Green Magic early in the year to get a event where she shows up at your dorm and calls you "Bej." After the Dark Dance look for Barbra. Fail the 3rd exam.
You have to be in the literature club (Be Co-President and talk to librarian about books and you'll get the option to start it instead of going to the hockey game) & the poetry club (Get Silence [Blue 7] before following William at night) and don't choose anyone at Christmas