From Harem to Heartbreak: TOP 7 Anime like Too Many Losing Heroines

Saekano: How to Raise a Boring Girlfriend follows a high school student who teams up with a group of gifted but quirky girls to develop a dating sim

Haganai: I Don't Have Many Friends follows a group of oddball high school students form a club to make friends, leading to comedic and romantic situations.

My First Girlfriend is a Gal is a humorous take on high school romance, where an average guy unexpectedly dates a popular girl, leading to romance and comedic misunderstandings

We Never Learn: BOKUBEN follows a student helps three girls with their studies, each one having different academic challenges and romantic feelings for him.

Watch "Nisekoi: False Love" for its charming blend of romantic misunderstandings and a quirky love triangle that keeps you guessing, much like "Too Many Losing Heroines!

My Teen Romantic Comedy SNAFU follows a cynical high school student is forced to join the Service Club alongside Yukino Yukinoshita, a sharp-tongued perfectionist, and Yui Yuigahama, a bubbly optimist with her own hidden motives

You might enjoy Oresuki: Are You The Only One Who Loves Me? as it offers a clever twist on romantic comedy and harem tropes, similar to the unique take you enjoyed in Too Many Losing Heroines!