AN: Chat has never flirted with Ladybug in this AU. Also, this is mostly me dealing with issues because my view on romance has been skewed. I'm writing this for me by living through Chat/Adrien. Also, the characters are aged up to 22 and Adrien never attended public school.

"Hello Ladybug". Chat greeted her with a small smile. Ladybug landed on the Eiffel Tower next to him and greeted him with a big smile. Tonight was a night for their evening patrol around Paris. Often times, the two would meet up on a rooftop and make some conversation before starting their runs and meeting back up again to brief each other. Occasionally, someone would bring snacks and drinks as an after patrol snack.

Patrols were done and Chat brought back some pastries and milkshakes. Ladybug smiled as she saw the pastries were from her family's bakery.

The two of them sat on a beam far off the ground, enjoying the view of Paris at night that only a handful of people could enjoy. Chat maintained a respectful distance from her and Ladybug frowned a little. In all of the years she had known him, Ladybug grew to trust Chat Noir and he was her best friend, next to Alya. Well, maybe even more than Alya since he understood the whole double life thing. They could vaguely talk about things in their personal lives to each other, but nothing revealing. While she did trust him with her life and would be willing to trust him more, there was something about him that was an enigma. Chat didn't talk too much of his personal life, but she never knew why. She always assumed he had some trouble at home and didn't push him if he didn't want to talk. But it made her feel sad and she could tell that her chaton was always hiding his hurt feelings and sadness behind the cheery façade. He didn't seem to have many friends since he never mentioned anyone. The people he talked about the most were usually co-workers and his father. Sometimes he mentioned his father's secretary as well, but not often.

Ladybug took a sip of her milkshake and put it down. "Hey Chat" she called over at him as he was sitting down with a support beam holding up his back. Chat looked over at her with a questioning glance.

Ladybug felt a little blush on her cheeks and looked away from his gaze. "Why don't you ever ask me out?" The blush on her cheeks grew brighter. She couldn't tell, but Chat raised a questioning eyebrow at her. She had dated before, with Luka, but it didn't work out. Fortunately, they had an amicable breakup and managed to remain friends.

Ladybug glanced at Chat out of the corner of her eye and saw an emotion of something flicker of his face before it disappeared. Chat took a sip of his milkshake, the sound making Ladybug feel even more nervous.

Chat put the milkshake down and gazed back towards the city. "Have you ever dated before bug?" he asked in a neutral tone. That probably wasn't a good sign.

"Yes" Ladybug nodded, her blush slowly disappearing.

"How did it go?" Chat prompted, but she had the feeling that he already knew the answer.

"We broke up, but it wasn't bad." Ladybug answered him.

"If you broke up, then obviously, something was wrong with the relationship." Chat said with a bitter tone. "People don't breakup if there are any issues. There's always something and it's always someone's fault. Time, money, and emotions are wasted. Couples argue. They say things and other people get dragged into the middle, having to pick up the pieces. It hurts them every time they have to do that." Chat's tone grew angrier the more he spoke.

He turned back her and gave her a sharp glare. Ladybug recoiled from the look and it softened slightly. Chat looked away from her again. "I won't lie. When I was younger, I did often dream of going out with you. But I learned that relationships aren't happy things. People are when they are single, but when they get a romantic partner, you better watch out. Romantic relationships are nothing but torture. A prison for everyone involved. They are just too blinded by rose-tinted glasses that they get married. Only then do the glasses come off and they understand how wrong they were. Then they just hope things will get better, but it never does. All they have is a false hope to cling to, and sometimes that's all that gets them through the day. Until it isn't enough and they just leave without a word. They hurt their partner and anyone else involved on their way out."

Chat's anger was very noticeable in his body language. Ladybug kept sitting on the support beam, too shocked to move. Sure she had seen and read fiction about people feeling bitter about love, but to actually hear from a real-life person is something else. Chat took a deep breath and continued.

"I am sorry to put this on you. I just have strong feelings about it." Chat admitted.

Ladybug gulped and tried to reassure him. "It's okay Chat. You can talk to me about this stuff. But maybe you don't have to…."

"Don't try to change my mind." Chat interrupted her. "I know what I said, and I know I meant it. I would rather die alone and single than be trapped and tortured like that. I've had years to think about this. It only ends in pain and misery." He finished.

Ladybug stared down at nothing as she processed this. "Is this related to why you always throw yourself in harm's way for me?"

Chat said nothing. He merely finished up his milkshake. "I think we're done for tonight. I'm going to go for a run for a bit, alone, and head home. Good night bug."

Chat made to leave, then stopped. "For what it's worth bugaboo, if reality isn't the way it is, I may have considered asking you out. I almost did once." Chat told her softly.

He jumped off the tower towards the rooftops of Paris. Ladybug couldn't help but feel a little pain in her heart for him as he left.

**adrien's parents fought a lot. He thinks his mom abandoned him. Called him a genetic mistake