Disclaimer: I do not own RWBY, Fate or anything you may recognise. All credits are to be given to their rightful owners.
Jaune, heading to Glynda's room to pick her up for their date. he was a bit nervous since he has never been in a date, he was just planning to bring Glynda to Menagerie, have a nice dinner then have a walk in the park. He just wanted to show Glynda a good time since she started to have more paperwork due to the students from other Huntsman Academy arriving, she has to complete paperwork for each of them and assign a dorm room for them to stay at, Jaune was thinking if there was anything he can make for her to help with her paperwork like a simplified version of JARVIS, giving her suggestion and typing the answer she is saying to help her complete the paperwork faster rather than her having to type everything.
After a few minutes of thinking he arrived in the front of her room and he knocked and waited for Glynda to answer when she did Jaune was mesmerized by the way Glynda look, her hair was styled in a fishtail braid, the clothes she was wearing was a navy blue blazer, a grey shirt, a brown stylish belt, a white pencil skirt and beige high heels, the only think Jaune could think of was 'wow' or 'beautiful'.
"You look amazing Glynda." Jaune told her which caused Glynda to blush since most people just see her as a strict teacher and nothing more.
"Thank you, Jaune. And you look great as well, why don't you come in for a bit." Glynda said to Jaune.
"Are you ready to go." Jaune asked.
"Yes, I am, just doing some final touches, and also I would like to apologise for the way I may act today Jaune, since this is my first date with anyone, ever, since I was very focused on being a huntress since a young age, so I did not really have time to go on a date and before I knew it, it was already too late, no one was interested in me since to the people and my colleague, I'm the strict teacher who won't tolerate anything and they think I'm married to my work." Glynda said to Jaune with sadness in her voice.
"It's okay Glynda and we should be having a good time today, so let's just enjoy ourselves, okay." Jaune said to Glynda to take her mind of the subject.
"Thanks, Jaune, so, what will we be doing today, you just told me that you would pick me up but did not tell me where we were heading." Glynda asked
"We are heading to Menagerie, we will first having dinner then we will head to a botanical garden, and lastly I just want to have some time getting to know you." Jaune said which confused Glynda since Menagerie not somewhere you can just go to if you were in Vale.
"Jaune, Menagerie is across the continent, how are we supposed to get there." Glynda said. Jaune did not say anything and just took out Yamato and opened a portal to Menagerie, and Jaune took Glynda's hand and pulled her through the portal.
Glynda was amazed by the beauty that was in front of her, Jaune did not just bring her to any place in Menagerie but he brought her to the botanical garden of Menagerie where a lot of its flowers are currently blooming.
"I hope you don't mind. I thought that since you are always busy, I should bring you here to have a relaxing time, have a walk and have some tea for the start of the date." Jaune told Glynda which got a smile from her since she was grateful for Jaune bringing her here.
"Thanks, Jaune, I appreciate it. Ozpin, may be the headmaster but most of his work are relayed to me, he would often say that he is busy to do it since he has other important things to do. But tell me Jaune, is this really Menagerie? The last time I heard about Menageries is that they are currently struggling with resources." Glynda asked Jaune.
"This is in fact Menagerie, all you have to do is look around and you will see that there are almost no Humans here." Jaune told Glynda and true to his word when she looked around she saw no Humans besides them.
Jaune took her hand and brought her around the garden, looking at the blooming flora. Jaune and Glynda have been walking and admiring the flowers for an hour before they decided to have a sit and Jaune took out his tea set with some tea leaves that he knows will help Glynda unwind and relax more. While drinking tea Jaune and Glynda decided to get to know each other better.
"So, Glynda, can I ask, what do you like to do when you aren't busy with work, any hobbies?" Jaune asked
"When I'm not being buried with work I just like to drink tea and relax while trying to clear my mind, what about you?" Glynda told Jaune.
"For me, when I don't have much to do I would sometimes train or sit down and write a book." Jaune told Glynda.
"What is your family like." Glynda asked.
"Well, I have seven sisters, three older and four younger, the oldest is Saphron she is four years older than me and is sometime quite spontaneous, then there is the second oldest Ivory she is three years older than me, she is a more level headed person and likes to analyse things, the third oldest is Viridian she is only a year older than me, she is the creative one in the family and she loves making art, the first youngest is Beryl she is a year younger and she loves cooking and sometimes would come to me to ask for some cooking advice since she loves my cooking, the second youngest is two years younger her name is Cyan she loves dressing in blue and loves making music she would mostly say that music is a part of our soul, the third youngest is Jade she is the dancer and is the twin of Cyan she would always try and get me to dance with her during her practice, and lastly the youngest of them all Olive she is four years younger and just wants to be a florist. My dad Giallo is a semi active huntsman, he only accepts work that is near our village and lastly my mom she is just a regular house wife who really loves her kids." Jaune told Glynda, who was now wide-eyed at the fact that Jaune has seven sisters.
"Wow, seven sisters, that must have been tough for you." Glynda said to Jaune.
"To most maybe, but it was not really that tough for me since I enjoyed our time together especially when they needed my help with something and they come to me instead of our parents." Jaune said to Glynda while smiling remembering his siblings.
"What about you Glynda, how is your family?" Jaune asked.
"Both of my parents have passed away years ago while I was studying at Beacon, the dispatched huntsman sent to there village to help take care of the Grimm was unfortunately a drunk and was not able to get in the location he was sent to due to being passed out in a bar, it was one of the reason why I'm quite irritated with Qrow since he used to always be drunk and it would remind me of the time my parents died." Glynda said saddened at the memories of her deceased parents.
"I'm sorry about your parents Glynda and for making you remember such bad memories." Jaune said very apologetically.
"It's fine Jaune, since you didn't know and I was the one who mentioned family in our conversation." Glynda said.
Over the next few hours, Jaune and Glynda got to know more about each other such as the fact that Jaune's parents do not know that he is a huntsman or the fact that Glynda hates coffee due to some embarrassing experience. They enjoyed themselves and when Glynda got hungry they went to a restaurant that Jaune got permission from the owner to use the kitchen since they have not opened yet and Jaune cooked a very appetizing Chaliapin steak, Beef Stew, and a Buche de Noel for dessert. They both enjoyed their first date and when they got back to Beacon Jaune walked Glynda back to her room and she kissed him goodbye and thanked him for a wonderful evening.