Whispered Promises ~ 14 Days of Love with Anna offers gamers a unique Sims experience by immersing them in a story where they spend 14 days of spring break with their childhood friend Anna. At the beginning, gamers are greeted with a cheerful “Good morning, senpai. Are you up yet?”, laying the foundation for a shared adventure. The heroine, voiced by Koharu Anna (CV.), is not only the protagonist's childhood friend, but also his girlfriend, which adds intimacy to the gameplay. The character, described as naive but expressive, is depicted as someone who has a deep affection for both the user and the title itself.

Throughout Whispered Promises ~ 14 Days of Love with Anna, users are faced with various scenarios, such as choosing a movie for a date with someone special. Even if the film turns out to be underwhelming, the lady's playful nature shines through as she suggests ways to make the best of the situation. Her mischievous side comes out when she encourages the gamer to engage in underground activities during a less-than-interesting movie. Dreams add an element of fantasy; users experience sensations that blur the boundaries between reality and imagination. The girl's flirting at these moments gives the interaction a playful tone, further deepening the connection between the gamer and the character.