If you're looking for anime similar to Are You Okay With a Slightly Older Girlfriend? (Light Novel), you might like these titles.
One rainy day, salaryman Amakusa Ryo is saved by a high school girl he doesn't know at the station. He later finds out that the girl is Arima Ichika. Ryo is somewhat of a womanizer and to repay her for saving him, he suggests giving her a kiss or going out on a date with her, in which Ichika tells him he's creepy. This, however, opens a new door for Ryo and he falls madly in love with her. Ever since then, Ryo tries to overly express his feelings to Ichika. Ichika just keeps insulting him and says he's being creepy, but he just seems to take it as her way of showing affection towards him...
The trials and tribulations of a single father, who one day meets the reincarnation of his deceased wife.
I hired a maid who has something about her I just can’t put my finger on. Sure, she looks great and is a fabulous cook, but something about her’s not quite right. What have I gotten myself into!?
Akira Tachibana is a reserved high school student who was the star of the track and field team but had to quit when she got injured. Sidelined and depressed, Akira stops in at a family restaurant one rainy day, and after the manager—a 45-year-old man with a young son—serves her free coffee, she is smitten, and soon takes a part-time job at the restaurant. Despite the age gap, Akira is drawn to his kind nature, and little by little, the two begin to understand each other. One day, she decides to finally tell her manager how she feels… but how will he react?
When Takao decides to skip school one day in favor of sketching in a rainy garden, he has no idea how much his life will change when he encounters Yukino. Older, but perhaps not as much wiser, she seems adrift in the world. Despite the difference in their ages, they strike up an unusual relationship that always occur in the same garden on each rainy day. But the rainy season is coming to a close, and there are so many things still left unsaid and undone between them.
High schooler Kaho Nikaido is having trouble adjusting to her new life in Tokyo. It doesn’t get any easier when she is nearly hit by a truck and saved by the handsome Kanade Takahashi! Infatuated with Kanade, she works up the courage to confess. But he warns that if Kaho learns who he is, she won’t want him. What could possibly keep her from this stud? Maybe the fact that he’s…a fifth grader?!
Diamond dust: when the moisture in the air freezes on a chilly day, the air seems to sparkle and shimmer. It is said that to see the diamond dust in its glory means that lovers will stay together forever, friendships will flourish, and dreams will be realized. Kita-he ~Diamond Dust Drops~ tells the stories of several groups of friends and lovers as they struggle to stay together, accomplish their dreams, and anything in between, all revolving around the tale of the diamond dust.
With Aoki-sensei’s birthday coming up, Rin, Kuro and Mimi decide to sneak into the school infirmary and take a look at his health record. Unfortunately Aoki catches them, but the gang manages to make a hasty escape once Rin stalls Aoki by flashing her panties. The trio - now armed with all the information it needs - heads to a department store in order to find Aoki the perfect gift... but not without being distracted by arcade games, ice creams and lingerie shopping along the way! Returning empty-handed, they then decide to have a sleepover at Rin’s house in order to make Aoki the perfect gift; will they succeed?