Sorry you're having issues, that sucks :/ Unfortunately I wasn't able to reproduce your problem on my end - I quickly tried playing through as a male character and got through the "Property of Trinity College" event and into the first Harper/Claire event ("The Point Guards") by going to the quad right afterwards. Is there a specific event you were trying to trigger while playing as a guy that wouldn't work past "Property of Trinity College"? Or was it the "Property of Trinity College" event itself that wasn't working?