Sekai Ichi Muzukashii Koi (2016)

Housewife Miyazawa Tomomi, her husband out of a job, loses her treasured home as her family is forced to do with less during the recession. Her one ray of sunshine is her upcoming middle school class reunion, where she hopes to meet old friends as well as old flames. The class reunion, however, turns out to be more of turning point not only for her but for the others as well. At the party, she reunite with her old friends Sugiyama Kosuke, Nishikawa Yoko, Okubo Shinichi. Just how will these four people's lives change after their class reunion...

Awkward male lead who tries various tactics to win the female lead's heart. Similar awkward leads, very comedy centric & romantic (in an adorable way)

Both star Haru in a romantic comedy that is set in a workplace, one in the fashion magazine business, one in the hotel business.

Both are japanese rom-com dramas about single president of the company in his thirties. They also give off similar vibes.

Written by the same screenwriter, they both share an well-paced, well-written script with incredibly witty dialog, lovable average-yet-quirky characters, and a delightfully awkward romance that blooms into something rather adorable.