For a first meeting, why not make it a bit dramatic? (TW)

"Don't worry, we'll stop by a shop on the way there and get you something nice," he said, no he wanted her to feel comfortable, but his eyes lingered on her for a short while, "though I wouldn't worry about your looks ... It's already perfect." He took another gulp of his tea, finishing it and his breakfast along with it. Where he had gotten the bravery to compliment her like that he wasn't sure, but he felt almost guilty for doing it. Selfish, even. She was a sweet promising young woman who had her whole life ahead of her, and he was but a lonely poet. Just thinking about that made him feel almost disgusted with himself.
After their breakfast, Simon made sure to clean up, "did you get your fill?" he asked, wanting to know if it had been sufficient. He wasn't that used to cooking for others, even if he enjoyed it. In his own posh family it was almost frowned upon that he was cooking, as they usually hired people for it. Cleaning up didn't take long as it seemed they had done a pretty good job at clearing out the plates, only a few miscellaneous items left that he gathered and sorted in to smaller containers for later. He was strangely aware of how much waste it could be to simply throw out the food when he could eat it just fine the next day.
He prepared himself for heading out, helping her find a jacket that perhaps would fit her somewhat as the weather outside wasn't too kind this time of year. "My lady," he said, a wide grin on his face as he was fooling around a little, holding out his arm for her to take. Once she did they headed out the door and down to the street level, heading towards the smaller yet more expensive stores up here in Northern. He let her decide which stores she wanted to enter and followed gladly, holding the items she wanted to try if need be.

Done with their breakfast, she watched as Simon cleaned everything up. It was such a mundane thing, a simple task most people either was used to or truly dreaded, yet at this moment it felt comforting. She felt almost at home in a way, as if her whole life she'd been standing on the outside, unable to get inside and yet here she was, invited to feel a sense of security for the first time in her life and it was addicting. She knew she couldn't stay forever and that her family would be angry with her, she could even imagine her mother's words, comparing her to that of a whore, or her brother that would probably either slap her or something worse. The thought made her clutch her wrist for a moment, memories of the past coming up, yet as she heard Simon's voice, it brought her back to reality and away from cruel thoughts "I did, it was most wonderful. Thank you," her smile was soft and tender as she looked at him, just allowing her brain to remember this moment, as she stood with him in his home, away from everything that would harm her. It was this moment she would think back to, as she laid alone in her bed, with no kindness to be around.
After having gotten the jacket on, she laughed at his sweet gesture of offering her his arm. Which she did put her own around, she probably shouldn't, yet she didn't want to regret not taking advantage of the moment and even leaned her head against his shoulder. As they got to the fancy clothing stores, she found one that appeared to catch her interest, quickly walking inside. She'd always been interested in clothes, yet not allowed to express herself through it, it would be considered too dangerous if she showed too much of herself or rather that had been the message of her father.
Inside the store, her blue eyes switched from clothing item to clothing item, until she found a beautiful white dress. It was long and yet elegant, it looked as if it could have been taken from a romantic painting "This one, I wanna try this one," she said giddy, quickly finding her own size, before then going to a fitting room. Once on, she admired her own reflection, before sticking her head out "Simon! How do I look?" she asked in a calling voice, removing the covers that had been giving her privacy before, now wanting his approval for this dress, that almost looked as if it had been made for her body. Her hair slightly more wild than usual, though still framing her face rather beautifully.

Simon was willingly following her, and in some ways he could see himself following her to the ends of the world. She just had this thing about her, something compelling, something that made her so loveable that in many ways he found himself so lucky to be around her. She was kind and smart, she spoke well and had a smile that could light up the whole room. Surely, he knew he was falling for her, and yet he felt inadequate. He was not someone she should've been associating with, not if you asked him. In many ways he was a coward, he knew that, because no matter how much he ended up caring for someone, he would never find the guts to tell them what they meant to him. Not truly. And she had been the light of his days. Each message had granted him a small escape from his self doubting and worrying. Every time she sent a smiley he could feel his stomach churn with excitement. And now she had spent the night in his bed, and he knew for damn sure that as soon as it was his turn to sleep later, he would be relishing in her scent.
He snapped out of his daydreaming as his name was called, her voice almost like a beautiful instrument that made him calm and yet alert at the same time. He moved over to the changing area, looking as she stepped forward, feeling a slight color to his cheeks. Lucky for him the weather outside had been helping with his cheeks and ears getting red, so there wasn't much of a difference right now. Except the feeling he got when he looked at her. "You look very wonderful," he said, trying to hold back all the sweet words he wanted to tell her. How she made him feel and yet guilt had taken over as soon as he thought of it. She wouldn't be happy with a sorry excuse for a man like him. She deserved much better than what he could offer, and yet he could not stop fooling himself and his own heart. "But I would dare to say that you always look wonderful," he added, smiling at her. Part of him so desperately wanted to reach out, touch her hair or maybe even say something meaningful.
"My only worry is ... Would it be warm enough?" he asked. Sure, the dress was long, but it was still cold outside. He didn't want her to forego her own comfort and wellbeing simply to dress nicely for a rehearsal. "But if you are set on it, maybe a jacket for getting to and from?" he wasn't going to be policing what she would or wouldn't wear. He was here to support her, and pay of course.