Disclaimer: I do not own nor will I ever own Harry Potter and Gotham.

Author's Notes: This is unbeta'd so all mistakes and typos you find are all mine. This fanfic is crossposted from AO3 and was written for Wizarding Crossover Bingo 2023, Harry Potter Crossover Versatile Prompt Fest 2023 , Cast the Dice 2023 , 30 Days of Crossovers Challenge and Melting the Pot's Tic Tac Toe 2023.

The character Oswald Cobblepot was requested by SnarkyGranger1

I used the following prompts:
- Engagement Ring
- Harry Potter/DC
- Proposal
- Villain/Anti Hero character

I hope everyone enjoys reading this!

Oswald Cobblepot, despite his dangerous occupation and the type of man he was, had managed to find himself a boyfriend. His boyfriend was a man named Harry who was handsome, interesting, and unique.

He and Harry had been dating for two years now.

Harry was twenty-eight years old, he was of average height and a bit taller than Oswald was. He had a lean build with some slight muscles and he had short, black hair that was untameably messy and a bit longer than Oswald's. Harry had beautiful green eyes, which were a shade of green that Oswald considered to be far more pretty than his own green eyes. Harry wore glasses which were round and black and he had a unique looking scar on his forehead that was shaped like a bolt of lightning.

Harry also had some scars on his right hand which he, usually in public were hidden by a pair of fashionable black gloves. Oswald had seen these scars and they were the words that said 'I must not tell lies'; the words appeared like they had been carved into Harry's hand repeatedly and Oswald was certain that if he ever met the person who dared to scar his boyfriend that he would kill them, as well as anyone else who had ever hurt the man who he was in love with.

Oswald had met Harry at a coffee shop back when he was still a lackey to Fish Mooney, back then he would go to the coffee shop to get a morning coffee for Fish. Oswald didn't like coffee much, he didn't like the taste of it, it was too strong of a taste for him usually but he enjoyed his visits to the coffee shop anyway.

Harry had genuinely smiled at him, Harry had been kind to him, he had ignored all the rude comments about Oswald from others and he had sometimes flirted with Oswald. Harry wasn't like other people, Harry liked him.

Oswald for a while was taken aback at the flirting, as it was rare that people would treat him with any positive attention, most people considered Oswald odd looking and creepy.

Not Harry though, no…he had seemed genuinely interested in him.

They had both developed romantic feelings for each other, though for Oswald it had been an awkward crush at first and then he had fallen in love with the barista.

Oswald had asked Harry out on a date and soon after that they were both in a relationship.

Oswald's mother approved of the relationship, she told Oswald that he finally had met a person who appreciated him for the smart and handsome man that he was.

Oswald knew Harry very well now, he knew that Harry possessed magical abilities and knew of Harry's past in England, knew how much Harry had suffered...and how it had changed Harry. Oswald had been shocked at first but then had quickly accepted Harry for the person who he was, for everything he had been through and still loved him.

How could Oswald not still accept and love Harry? Harry had accepted him and had fallen in love with him. Despite all of Oswald's flaws, despite all the bad things that other people would say about him Harry had accepted and loved Oswald.

Harry was good for Oswald, when Harry was with him he felt safe, he felt happy, he felt wanted and he felt normal. When Harry was around him Oswald would always make an effort to be a better man and to be a good boyfriend.

He was sure that Harry could do much better than him, but even so, now that he had Harry as his boyfriend, he would not let anyone else have him.

Which was why he was planning to propose.

One night, a couple of weeks after he had made this very important decision he and Harry had a date at Oswald's nightclub.

Oswald felt nervous and he felt scared. What if Harry didn't want to marry him? He knew that Harry was in love with him but would Harry want to live the rest of his life with him?

When Harry arrived for their date Oswald was still nervous and he was still scared at the response he would receive but he was determined.

"Oswald, is there something wrong? You seem incredibly nervous tonight." asked Harry as he started to eat.

Oswald smiled, "Yes…Yes, I guess I am feeling a bit nervous but do not worry my love , nothing is wrong. I just..just want to ask you something very important."

"Oh…really? What is it?"

Oswald took a large sip of wine to calm down his nerves, negative thoughts and fears and started to speak.

"Harry, when…when I'm with you I feel like I'm…normal, my mind feels almost peaceful and I'm happy. I love you..I love you so much. You…You are amazing, you are smart, handsome and you are a better man than I deserve, but even so…I..I…want to keep you"

Oswald stopped speaking and got out a small box out from a pocket and opened it up before presenting it to the man he was in love with. Inside the box was a ring designed for men that had diamonds embedded into it.

The gangster stared across the table, Harry looked like he was surprised and shocked but Oswald was relieved to see that it was in a happy sort of way. A smile was appearing across Harry's face and there were tears starting to form in his eyes.

"Will you marry me?" asked Oswald.

Harry was crying now but he nodded and said, "Yes Oswald, yes I will."

Oswald smiled happily, tears of relief and happiness fell down his cheeks.

Harry extended a hand to the gangster and Oswald happily put the engagement ring onto his boyfriend's finger.

Oswald then leant across the table and pulled his wizard boyfriend in for a kiss, happy that Harry had accepted , already feeling excited to live a life together with the man he was in love with.