 If you liked
Ookami to Koushinryou
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 ...then you might like
Sugar Apple Fairy Tale
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Both of this anime gave me similar vibes, while one of them is more romance heavy and features younger protagonist than the other both journeys with their 1000+ years old companions are pleasant to watch. Seeing how they overcome different difficulties on their path to fulfill their dreams and fall in love is very heartwarming.
- Protagonist that has very good knowledge in their respective field, but still have a space to grow
- 1000+ year magical companion love interest
- Apples
- Traveling around the contry, quite fast time progression
- Interesting world, with economy that impacts the story and main character job
- fantasy setting
- both include a male & a female character traveling together
- Both are romances set in a historical fantasy world.
- Both are bittersweet romances between an human and a sassy creature of magic who travel together by wagon.
- Both humans have a craft they're an expert in, and both series explore it. Medieval economics for Lawrence, Sugar sculpting for Ann.
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Recommended by Floral_soap