Can you lose virginity with best friend? I can't advance in their quest.
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You can develop a relationship with the best friend by either advancing the quad party storyline (don't wanna give spoilers) OR by taking a shower in the morning, which has a chance to trigger an event that also leads to a romance path with the best friend. After that morning shower your second encounter will happen randomly at night as you go from the main hall to your dorm room. And then just keep up talking about sex with them in their room. If still nothing is happening try hanging out with them in places like the arcade and the gym and wearing tight/revealing clothing to raise their lust, or dinner and movie hangouts to raise their romance.