Name: ARandomWeirdo

Age: 22

Some Recommendations:

Kara no Kyoukai: Garden of Sinners by Ufotable studios. Part of the Type-Moon universe, which includes the Fate series. I watched the anime and was completely awed. 7 episodes, about 9 hours total. Psychological and supernatural. I recommend it for mature audiences only. There was some dark stuff. The first episode is kind of slow, but the series speeds up really quickly.

Fate/Zero, based on the light novel by Gen Urobuchi and also by Ufotable studios and part of the Type-Moon universe. The Fourth Holy Grail War, a more typical Grail War with skilled adult magi as Masters. Heroes of legend clash to obtain the wish-granting device, the Holy Grail.

Angel Beats! A high school in the afterlife, populated with young souls unable to accept their cruel lives. Primarily action, comedy, and drama, it's a weird mix of multiple genres that somehow works.

Mahou Shoujo Madoka Magica/Puella Magi Madoka Magica. 12 episodes total. A dark deconstruction of the magical girl genre, and the idea that love and justice always wins. The first two movies summarize the 12 episodes, and the third movie is a sequel.

Princess Tutu. A magical girl series set in a fairy tale with ballet. The first half may seem like the typical Swan Lake tale, but the second half is where lines blur and the titular character, a determined duck, tries to break the story and avert tragedy.

Magi. A world of magic and kingdoms inspired by 1001 Arabian Nights. Wonderfully fleshed-out characters with rich backstories.

Undertale by Toby Fox. A great indie RPG for the computer. It has compelling characters, multiple endings, and a great sound track. It's can get rather meta, and it's fascinating how it's impossible to fully learn about characters or the story unless you take different actions in different playthroughs. What I enjoyed most was how your actions truly affected the characters and their reactions towards you. The real draw is the rich story and how invested you can get in the first playthrough. I would suggest you try and avoid spoilers until after your first playthrough for best results