clover doesn't have an exact type for one night stands (as long as they're not ugly and not a complete sleazeball), so i would be down for them having a one night stand that she'll pretend never existed.

JAN.... honestly, if clover finds out he slept with rose, she'd likely misplace her issues into thinking very poorly of kiryu. she does try to keep a nice and pleasant face on 95% of the time, though. one of her sisters in canon is a wholly good person who wants to take care of orphaned children, and four still finds bad things to think about her, so it could definitely happen.