Sanrio Danshi

Both shows involve adorable boys embracing their femininity. While LOVE! takes this is a more light and humorous tone, turning the stereotype of overly-masculine heroes and flipping it on its head, Sanrio Boys takes a more down-to-earth and realistic tone, showing the unfortunate consequences of people expressing themselves in an abnormal way.  

Both anime are about a group of cute guys becoming friends and bonding over a special interest (sanrio/theater). Both anime have the theater element. 

Similar plot/ set up  

Both anime are about the wholesome day-to-day little adventures of a group of pretty and quirky boys. 

Both shows offer commentary on gender expectations. While Sanrio Boys takes on a more serious tone, Ouran Highschool Host Club has a mostly light and comedic approach. Ouran also is more open to addressing gender and sexuality directly by mentioning the LGBT community while Sanrio Boys stays away from that topic in favor of discussing femininity in boys specifically.  

If you enjoy the very rare Cute Guys Doing Cute Things trope in anime, then this recommendation is up your alley. Not only do we see young and cute boys partaking in activities considered traditionally as feminine, but you also get to see them grow closer to each other as of their interest and involvement in said activities.  

Wholesome boys being boys!! If you like one or the other, they're both pretty sweet, surprisingly emotional and funny stories about friendship between a group of pretty diverse boys.  

Both shows focus on a group of people completely unrealted, who come together through a common interest. They're both more coming of age feel good relax stories, rather than massively plot driven ones  

It was Sanrio's beach episode that made me make a connection between that show and Free. On the surface, it might seem that both shows are very different (and honestly, they are), but what makes them similar to each other is the same basic premise - how a group of boys become closer to each other emotionally, based on a mutual passion that they (and only they) share. Initially, the boys aren't taken seriously and are even ridiculed for their passion, but they persevere and while doing so, they become even closer to each other. So if you enjoy seeing 17 year old boys bond with each other, then I'd highly recommend this series to you! read more