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Hi guys,
The game I'm talking about was lost when the website it was hosted on was bought by another company, I believe. Graphics were cartoonish. Each character had a sprite but when you talked to them, an illustration would appear.
You could control your character and have them walk around their small town, composed of the suburbs, the city center, and a more industrial/artsy area to the far left. I believe you were supposed to be the new guy/girl in town.
The first character you met was a cool lesbian barista. She had short hair, dyed a funky color (it could have been purple) as well as piercings and tattoos. She introduced you to the game concept. You could ask different questions and choose between different replies which would affect how your relationship changed.
A bit further down the street there was a clothes shop where you met your nemesis, the typical beautifully blond mean girl. I believe a mini game triggered at this point, but I can't remember what it was like. Winning would mean you outsmarted her rather than have her humiliate you. This character was not dateable.
The game was short and could be finished in a single sitting, as was typical of flash games.
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