James Gordon
Jim has always been known to have a rough exterior, but he does have emotions; he isn't inhuman. One particular case truly got to him: Alice Tetch. Seeing that poor girl suffer at the hands of her own brother, containing a virus within her blood, as well as failing to save her nagged at his mind. It got to Jim so badly that he began having nightmares about it. Some were insignificant, but others were frightening. When he'd have those kinds of nights, he usually began screaming and crying in his sleep, alarming you of possible danger. Of course there'd be no danger, just Jim. The first time you saw him cry in his nightmare, it made you cry. You hated seeing him so upset. So you got him to break his tough guy exterior and tell you what was bothering him so bad and why. Now when he cries, he goes to you.

Oswald Cobblepot
Oswald is a very emotional man overall, but the one time you ever saw him cry was when Galavan murdered Gertrude in front of the both of you. It was a sore sight to see. She may not have particularly liked you at first, but she became like a second mother to you. Hearing Oswald cry over her body made it even more unbearable. All you could do was hug him and comfort him. You don't have to say anything really, just be there for him and be his shoulder to cry on. Literally.

Jerome Valeska
You never knew Jerome when you two were kids; only when he murdered Lila. Other than the feigning of innocence act he put on for Gordon and Thompkins, he's never actually shed a tear. But...there was one time that you'd gotten hurt that he actually cried. He felt guilty of it (even though he had nothing to do with it) and sobbed like a baby. When you came home, you promised not to tell a soul that he actually cried...especially Greenwood.

Ed Nygma
Ed cried most of the time, considering he's always put down by Kristen Kringle, Captain Essen and Detective Bullock. Whenever they'd belittle him he'd come home to the apartment, already in tears. It breaks your heart to see him like that. You couldn't help but feel useless; you didn't work with Ed. You wanted the harassment to stop but what could you do about it anyways? So you just held him, whispering sweet little nothings into his ear all night long.

Bruce Wayne
The only time you've ever seen Bruce cry is when he witnessed his parents' murders. Though he cries at night due to nightmares, you've only seen Bruce cry at that one event in his lifetime.

Alfred Pennyworth
After Thomas and Martha were murdered, Alfred was struggling to raise Bruce as his own. "I just can't do it! I don't know how Master Wayne and Mrs. Wayne did it!" he stressed. "Love it's okay." you said gently, rubbing his back while doing so. "What if he gets hurt? What if I can't protect him? What if he ends up like Thomas and Martha?" Alfred questioned, the tears rolling down his cheeks. You looked him dead in the eyes and kissed him passionately. When you pulled away, you dried his tears. "Don't cry love. If you cry then I cry. You're doing an amazing job with raising Bruce. Don't stress yourself out; it's a natural instinct to worry. But I'm here for you all the time." you reminded him. He nodded and kissed your forehead. "I love you darling." Alfred said before walking off to the kitchen. "I love you too." you said as he was out of earshot.

Victor Zsasz
Are you kidding? HE'S VICTOR ZSASZ FOR CRYING OUT LOUD; HE DOESN'T EVEN KNOW HOW TO CRY!

Jonathan Crane
Jonathan has never cried in front of you...until now. He had just gone through another episode of scarecrows. He was sick and tired of seeing them and he started crying. You couldn't help but hold him close and kiss his head. Jonathan was hurting and you didn't know what to do except be there for him in any way you possibly could be.