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I think I've found the bug for Lexi.
The conditions to be met are "Lexi => nightclub" and "Sasha => Night Club"

The first will be checked green when I'm there with Lexi on a date. But then, there's no other room or person accessible. 

The second will be checked green when I'm on a normal night out in the club, dating no-one, but seeing Sasha there. 

Had that confirmed when I met Lexi and Sasha on a normal night in the club at the same time...

Means: both events can't trigger at the same time. This could just be due to the different spellings of "nightclub" and "night club"...