The phrase "to lose both sides" means failing to satisfy or please both parties involved in a situation, resulting in negative consequences or outcomes for oneself. Full definition
While some couples seem to function okay without that component in their marriage, others definitely notice that lost side of marriage, and negative feelings start to follow. (marriage.com)
Sadly, the legacy of this referendum could be a knee jerk rejection (from those on losing side) against all referendums. (democraticaudit.com)
Capturing a precarious moment in American history, Daniel Barber's film focuses on the ravaged losing side in the immediate aftermath of the American Civil War, and on the young inheritors of that destruction. (lwlies.com)