Let's see I hate spoiling it BUT I would much rather you see him because I'm super proud of Ashton's dates, so below are SPOILERS
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If you still have the .txt file from the first picture perfect boyfriend game that Ashton leaves you, put that file into the WWW folder of Reboot. If you don't have it you can make a regular text file and name it BAiHR_Survey and put that into the folder (just pretend its the file Ashton left you hehehe)
However something still stops you from meeting him, you'll have to complete Kadsey, Vincent's, and John's TRUE ENDS to unlock red eyed Ashton's true end. When he's done being a drama queen go and try to date the REAL Ashton
If any of that doesn't work please let me know!