Appriciate it Fellers, the guide is really fucking me up and making me start over for no reason because i dont wanna miss anything.
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Most girls are fairly straightforward to romance. The exceptions are Amber and Emily.
Amber:
She is the only romance which needs both a correct choice and has a relationship point check. You need 3 relationship points for the "I love you" option to appear, and you have to choose it when you see it. Other choices do not matter. however the game tracks if you supported her when she comfronts her mother.
Emily:
Her romance starts during the main quest, not her side route. At some point you will play poker with Alice and Deryl. In this event you will meet Emily. If you have sex with her, it sets the "emkiss" variable to true. Choices made during her side route do not affect her romance in anyway.
Tess:
Accept her advances. Fairly straightforward.
Jess:
Make sure you tell her your secret.
Liz:
You can't really fail her romance. You only have to decide if you want the romance route or the NTR route. While the NTR route is supported, it doesn't count as a successful romance. There are 2 choices tracked by the game, and they have to do with MC telling Liz if he agrees with how she views herself. Up till this point it doesn't affect the romance.
Demi / Angelina:
Again I don't think it's possible to fail their romance. Just don't kill them / let them die.
Tiffany:
Her romance happens during the main quest. At some point she asks you to take her virginity, accept and that's it. Later at her wedding you have the option of having sex with her although it's easy to miss.
Brianna:
The first 2 times you have sex with her for free (during the prison segment and later during an interview). The next you need 3+ relationship with her which pretty much sets the romance to active. Make sure you guilt trip her during the prison segment. She likes it.
Alice:
After beating Klaus, you have to insist in dating her when she tries to dissuade you.
Bailey:
Make sure to not kill her before she asks you to.
Keeping those in mind and following the walkthrough should allow you to get the most content.
The optimized playthrough is to prioritize Liz romance till the first sex scene(more relationship with Jake later), and the cheerleaders up to getting 5 skill points (better scene against Klaus). The rest do not really matter.