Games like Endless Monday: Dreams and Deadlines
Games like Endless Monday: Dreams and Deadlines include The Henry Stickmin Collection, Undertale, Far Away, NEEDY STREAMER OVERLOAD, and Refind Self: The Personality Test Game. We matched them by the tags players give Endless Monday: Dreams and Deadlines on Steam (Visual Novel, Choose Your Own Adventure, Interactive Fiction, Hand-drawn, and Choices Matter): closest matches first, and among equally close ones the better-known games.

The Henry Stickmin Collection
Shared: Choose Your Own Adventure · Multiple Endings · Choices Matter

Undertale
Shared: Choices Matter · Multiple Endings · Pixel Graphics

Far Away
Shared: Visual Novel · Choices Matter · Choose Your Own Adventure

NEEDY STREAMER OVERLOAD
Shared: Visual Novel · Anime · Multiple Endings

Refind Self: The Personality Test Game
Shared: Visual Novel · Interactive Fiction · Choose Your Own Adventure

Suzerain
Shared: Visual Novel · Choose Your Own Adventure · Interactive Fiction

The NOexistenceN of you AND me
Shared: Visual Novel · Multiple Endings · Interactive Fiction

Slay the Princess — The Pristine Cut
Shared: Visual Novel · Choices Matter · Choose Your Own Adventure

I Wani Hug that Gator!
Shared: Visual Novel · Choose Your Own Adventure · Choices Matter

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

BAD END THEATER
Shared: Visual Novel · Multiple Endings · Choose Your Own Adventure

Love, Money, Rock'n'Roll
Shared: Visual Novel · Anime · Multiple Endings

The Wolf Among Us
Shared: Choose Your Own Adventure · Visual Novel · Choices Matter

Otaku's Adventure
Shared: Visual Novel · Multiple Endings · Funny

The Test
Shared: Choose Your Own Adventure · Multiple Endings · Visual Novel

LoveChoice
Shared: Visual Novel · Choices Matter · Multiple Endings

Mirror 2: Project X
Shared: Visual Novel · Interactive Fiction · Anime

The Life and Suffering of Sir Brante
Shared: Choices Matter · Interactive Fiction · Choose Your Own Adventure

Volcano Princess
Shared: Choices Matter · Multiple Endings · Visual Novel

OneShot
Shared: Choices Matter · Cute · Pixel Graphics

Doki Doki Literature Club Plus!
Shared: Visual Novel · Anime · Cute

Class of '09: The Re-Up
Shared: Visual Novel · Choose Your Own Adventure · Anime

Late Shift
Shared: Choose Your Own Adventure · Choices Matter · Interactive Fiction

The Weeping Swan: Ten Days of the City's Fall
Shared: Interactive Fiction · Visual Novel · Multiple Endings