Oswald was sitting behind his desk at the Iceberg Lounge, his forehead scrunch up in concentration, looking through the clubs accounts. Though glaring might be a more accurate description. The club was doing well but the Bat had caused significant damage to the VIP area earlier that night. His liquor stock destroyed, multiple staff in hospital, his bar counter in splinters and 2 walls knock out all because The Joker decided to throw Harley's birthday party at the lounge. The Penguin and The Joker are close allies, they work together regularly, and have developed a close friendship based on mutual respect, but Oswald can't stand Harley. Her mere presence irritates him, every time she speaks he wants to stab her in the throat, and he cannot forgive that she has repeatedly hurt the one person left he still considers family, Ivy. Oswald wholeheartedly believes that you don't let personal dramas impact business, but it's his shoulder that Ivy cries on whenever Harley runs back to Jerome, so Oswald refused to host the party. The Joker took the refusal as a personal insult and despite Oswald's best efforts he could not convince otherwise unless Oswald hosted the party. The party itself would have gone fine, but The Joker just had to rob the Gotham national bank, to bankroll the party, just prior to attendance. Which meant the party was soon crashed by the Bat. Which left Oswald in the difficult position of trying to work out how he was going to afford repairs since the majority of income was currently tied up in his other, less than legal, enterprises.
After hours of getting no where Oswald decided he needed a drink. Oswald reached for the bottle of vodka inside his desk draw and took a swig. Now Oswald may be known as the dapper gangland kingpin but he could admit he could be as low class as his lowest henchmen, and drinking straight from the bottle was definitely low class. After a couple of swigs Oswald decided he wanted a distraction. Oswald sent a summons for the clubs new bartender. Though to be honest they're always relatively new. The Iceberg Lounge had a high turnover rate as staff either left because of the constant chaos resulting from the Bat and the rogues gallery, died in some bizarre circumstance, or if they had ambition they would find a way to advance in Oswald ranks.
Oswald had his choice of men, or women, who would crawl on hands and knees to be with him. This wasn't vanity, he knew he was not what anyone would call conventionally attractive, but he was rich, powerful, respected and feared. These were traits to be desired in Gotham. Despite this he found he prefered to keep sex casual, almost contractual in nature. Firstly, as he felt it reduced the possibility of a blade, or bullet, in the back. No one was able to betray you when they didn't have access to anything that could be used against you and they can't be used as leverage if the only thing between you is the exchange of a material reward for services rendered. No messy emotional entanglements. He will never let love be a weakness again, he learned that lesson already. Secondly, he is sadly still in love with Edward ‘The Riddler’ Nygma. Oswald took another drink from the vodka bottle, snorted and muttered “God what a ridiculous name”.
On bad days, and this was looking to be one, when he had too much to drink he would end up reflecting on his life, particularly Ed’s role in it. Oswald always regretted when he indulged in this kind of self pity, it only lead to embarrassment and dead henchmen. The drinking would lead to obsessing about Ed and end in him ranting or crying pathetically at one of his henchmen, and then he would have kill the unfortunate idiot who witness his weakness. It was a complete waste of resources, but hey who was he to deny himself anything, even self pity.
Their feud didn't last long, he always knew it wouldn't. Oswald was victorious, he reclaimed his throne and Ed was put on display in the Iceberg Lounge as a reminder to Gotham about what happens to those who cross The Penguin. However he eventually found a reason to defrost Ed, one that could not be perceived as weakness or sentiment. He was honest that day on the docks when he said they needed each other, and despite his best effort he could not envision a reality without him. Ed had been humbled by the experience, he never dared challenge Oswald again, but would not work under him. They became uneasy allies at best, and only when required. However Oswald's position as the head of Gotham's underworld and prominent society member, along with his friendships with other notable rogues, meant Ed would not be able to avoid the association even if he tried.