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Lee Jae In is the grandson of a wealthy businessman, but prefers to make his own way. However, when his grandfather offers to give him his fortune if he will marry a kindly school-teacher, Jae In investigates.

Jae In negotiates his grandfather down to just dating Kim Da Hyun for six months in order to secure his position. The problem is that Da Hyun still isn't convinced.

Jae In and Da Hyun solidify their agreement and draw up a contract, followed by their first official date.

Chairman Lee is eager to hear news about the relationship, but the rest of the family are not too happy.

Jae In decides that if he is really going to date Da Hyun, he needs to step his game up and do the things other couples do.

A bomb scare keeps Jae In from keeping his date with Da Hyun, making her reevaluate her feelings about their relationship.

It is Jae In's birthday, and their awkward relationship makes finding the right gift a nightmare for Da Hyun.

A robbery at Da Hyun's apartment forces her to stay at Jae In's place, further clouding her mind with temptation.

An old paramour of Jae In drops in to make a business proposal, and Da Hyun doesn't like it.

Both Da Hyun and Jae In face obstacles from outside their relationship that make trusting their partner hard.

Da Hyun formally meets Min Tae Ha, and Jae In is forced to fess up about hiding the last page of his dating contract.

Da Hyun disappears when a shadowy figure decides Min Tae Ha deserves to inherit SH Group.

After the kidnapping, Da Hyun must deal with her PTSD, and Jae In vows to exact revenge on the kidnapper.

The last day of their contracted dating passes, and the couple separates.

Da Hyun and Jae In deal with being apart, and going on blind dates.

In the finale, Jae In and Da Hyun must navigate their remaining obstacles in order to marry each other.