"Omiai Aite wa Oshiego, Tsuyoki na, Mondaiji" is a romantic comedy manga that centers around the unconventional relationship between a high school teacher and her former student. The protagonist, Ichika Tachibana, is a dedicated and hardworking teacher who finds herself in an arranged marriage meeting with her former student, Hayato Sajou. Hayato, now a successful and confident adult, harbors long-standing feelings for Ichika, which he had suppressed during his school years. The story explores their evolving dynamic as they navigate the complexities of their past and present relationship.

Ichika is portrayed as a responsible and caring individual, often prioritizing her students' well-being over her personal life. Her initial reluctance to engage with Hayato stems from her professional boundaries and the societal expectations surrounding teacher-student relationships. Hayato, on the other hand, is determined and assertive, using the arranged marriage setup as an opportunity to express his feelings and pursue a romantic relationship with Ichika. His persistence and maturity challenge Ichika's preconceptions and force her to confront her own emotions.

The narrative delves into themes of personal growth, societal norms, and the blurred lines between professional and personal relationships. As the story progresses, Ichika and Hayato's interactions reveal layers of vulnerability and mutual respect, gradually bridging the gap between their past and present selves. The manga balances comedic moments with heartfelt scenes, creating a nuanced portrayal of their journey from teacher and student to potential life partners. Supporting characters, including colleagues and friends, add depth to the story by providing contrasting perspectives and contributing to the central conflict. The series maintains a lighthearted tone while addressing the challenges of redefining relationships in the face of societal expectations.