Omoi, Omoware, Furi, Furare

- both stories are about teenage romance where the MC is waiting foe the love of her life - they are both done by the same mangaka so if you enjoyed one you are more likely to enjoy the other - both are romance/school/ drama - the characters personalities are quite similar  

School, Drama and Romance movies focusing on multiple relationships instead of the standard one with relatively reminiscent character archetypes and character dynamics alongside it 

Both are movies and they both have a short haired main character who regrets things from their past. They both have romance but Omoi, Omoi, Furi, Furare focuses more on romance while Ai no Utagoe wo Kikasete focuses more on AI's and technology. Both movies also take place in a school. 

Both of these animes feature Otaku romances, however, Omoi is a movie with multiple couples with more of a focus on drama while My Dress-Up Darling is more ecchi and comedy focused.  

The main heroines are both similar. They are shy and both want to make friends at the beggining. They both fall in Love with someone who is popular. The only difference is Omoi, omaware, Furi, Furare is more of a love triangle while Kimi ni Todoke mainly focuses on the main pair. Also while Kimi ni Todoke is like two 25 episode seasons Omoi, Omoware is a 2 hour movie. 

Nisekoi: - Amano = Chitoge - Segawa = Onodera Koi to Uso: - Amano = Ririna - Segawa = Misaki Omoi Omoware Furi Furare: - Sachi = Rio (same complex) 

"Love Me, Love Me Not" is remarkably similar to "A Lull in the Sea" but without the "sea/ocean" concept. From friends to lovers, confession, rejection, unrequited love, and a five-way romance. If you like all or most of those things, then I think both can provide the same feeling to you as it starts as funny and proceeds to become dramatic over time. 

Great anime romance movies to watch for relaxing and passing the time as they are lighthearted, short, and aren't too heavy for the heart yet can still give the same sensation as other dramatic romance films can do. Moreover, I think that the premise and setting are highly similar; a tale about a young schoolgirl who cannot confess to her crush. I recommend both for those who want to watch a non-depressing melodramatic romance film. 

Both anime build similar romantic tension between the step-siblings/main characters by following their lives after their parents marry together as they now have to live together