Games like Head Over Heels
Games like Head Over Heels include LoveChoice, Sweet Home, Volcano Princess, Class of '09: The Re-Up, and 小白兔电商~Bunny e-Shop. We matched them by the tags players give Head Over Heels on Steam (RPG, Simulation, Casual, Dating Sim, and Interactive Fiction): closest matches first, and among equally close ones the better-known games.

LoveChoice
Shared: Dating Sim · Visual Novel · Simulation

Sweet Home
Shared: RPG · Visual Novel · Interactive Fiction

Volcano Princess
Shared: RPG · Dating Sim · Simulation

Class of '09: The Re-Up
Shared: Visual Novel · Casual · Simulation

小白兔电商~Bunny e-Shop
Shared: Dating Sim · Simulation · Visual Novel

ERROR143
Shared: Dating Sim · Casual · Simulation

Emily is Away <3
Shared: Simulation · Dating Sim · Casual

Tricolour Lovestory
Shared: Dating Sim · Visual Novel · Simulation

Doki Doki Literature Club Plus!
Shared: Dating Sim · Visual Novel · Anime

Fields of Mistria
Shared: RPG · Dating Sim · Simulation

Vampires' Melody
Shared: Casual · Visual Novel · Interactive Fiction

Lucy -The Eternity She Wished For-
Shared: Visual Novel · Dating Sim · Anime

Hua Manlou
Shared: Simulation · RPG · Casual

Senren * Banka
Shared: Dating Sim · Visual Novel · Casual

Chinese Parents
Shared: Simulation · RPG · Casual

STORY OF SEASONS: Friends of Mineral Town
Shared: Simulation · Casual · RPG

鬼谷八荒 Tale of Immortal
Shared: Simulation · RPG · Dating Sim

ATRI -My Dear Moments-
Shared: Visual Novel · Dating Sim · Casual

The Hungry Lamb: Traveling in the Late Ming Dynasty
Shared: Visual Novel · Interactive Fiction · Dating Sim

Billionaire Lovers
Shared: RPG · Visual Novel · Casual

他人世界末 On-looker
Shared: Dating Sim · RPG · Visual Novel

FEMBOY FUTA HOUSE
Shared: Simulation · RPG · Visual Novel

Love Delivery
Shared: Simulation · Dating Sim · Casual

Touhou Mystia's Izakaya
Shared: Simulation · Casual · RPG