Freelance work is never easy — just as the creatives tasked with completing edit after edit after edit while getting paid pennies for their blood, sweat and artistic tears. Yet as several artists know, not all gigs are created equal — some of which come with the added perk of being so terrible, they fuel horror stories for years to come.

From extremely awkward commissions to patrons trying to flirt their way out of the bill, here are 23 of the most horrifying things artists have endured in their entire freelance careers.