That's weird, as 2nd option should be unlocked after the 1st one, so looks like a bug. Will look into it. Thanks for reporting!
The option to "drink at the bar" from Ben's room is also unavailable.
What do you mean? The event you screenshotted is from that dialogue choice, so it has to work... Open Event Sheet (Y button) and search for "Ben 101" in search bar - you will have the event requirements there.
it doesn't matter. I was wrong. It's working. sorry.
