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 OptionsEdit
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 KenyonEdit
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 InteractionsEdit
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.