The Zashiki Warashi of Intellectual Village - Volume 5, PACKAGE_Console_System_Ver.010.56.

Coming to my senses... I find myself a desperado.In the depths of azure, black sails flutter.Treasure gleams, blades ring out.Pillage, slaughter, irreverence towards the gods.Youth fades swiftly, all but meat and wine for pleasures.[Slice of Life][Romance Simulation][Business Simulation]

The 7-year-old little crybaby met 11-year-old big brother who ran away from home.
[This man became the protector of redemption in his life]

The 16-year-old little dragon fell in love with a 20-year-old big brother.
[It’s a pity that the big brother didn’t recognize him as the little crybaby]

The 23-year-old single father and 27-year-old chief executive meets again.
[This time the little crybaby and his big brother are finally together]

Fortunately we met through hundreds of millions of people, Thank God, for letting us break through many obstacles and get back together again, falling in love with you and being with you again is the greatest fortune in my life.

- Description from Novelupdates

He died on the wedding of the girl he had a crush on, after a long and successful career. After convincing Yama to send him back to the world, he decides to fix the areas in which his life went wrong. Realizing the lack of love and romance in his past life, he sets out to conquer the hearts of various women.