ORS Route Guide: Ian x Cherry (Patreon)

Flirt
During Chapter 2, Ian goes to the cocktail bar Shine with Alison, Cherry, Jeremy & Perry. You need to "Stay with Cherry and Perry" and "Break the ice". Then "Keep chatting with Cherry" and follow it by "You don't look like an office worker" or "What are your hobbies?". While Jeremy gets closer to Alison "Maintain eye contact with Cherry" and "Keep flirting".

Date
Not compatible with Alison's route
During Chapter 3, when she tells you she's not looking for a relationship, answer "I see it that way too" and, as long as Ian doesn't have sex Alison during Chapter 5, she'll open up to him during Chapter 6 .
If you choose "I thought we could be more", you'll miss her selfies but you'll still be able to "Push for another chance with Cherry".

Love
Not compatible with Lena's Love route
When Ian receives her text during Chapter 9, agree to "Meet Cherry". During the date, answer "I'm sure you didn't do it on purpose" or "Why did you do it?" and "Comfort Cherry". Then, if Ian is dating Lena but not in love with her, tell her "She's just a friend" which allows Ian to "Continue to date Cherry". If he's not dating Lena, simply "Invite Cherry home".

Nothing more for now but we can expect their relationship to go further.