Mid-90s synth that somehow makes high school feel like the most important thing in the universe. Tokimeki Memorial on PS1 and Saturn basically invented the dating sim genre, and the soundtrack carries so much of why it worked.
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Bloom captures spring with this bright, hopeful melody that cycles through your head during stat-grinding sessions. Shiori Fujisaki's theme Just a Few Memories is the one everyone remembers, gentle piano over soft pads that hits completely different once you've actually reached her ending.
Footsteps on Dry Leaves does autumn melancholy perfectly. That seasonal rotation of music made the whole three-year structure feel real. If you've ever wondered why people got so attached to dating sims in the 90s, listen to this and you'll understand immediately.