The 100 Girlfriends Who Really, Really, Really, Really, Really Love You
I'm not usually the type of guy to enjoy harem comedies, but 100kanojo makes it so damn easy. The first thing that really smoothed the read for me is the main male character, Rentarou. He's the harem's protagonist, and I love him. Why? Because unlike most harem protagonists, he truly expresses joy when in the company of the harem, and not just because he's horny. Rentarou is a lovable idiot, whose earnest adoration for each of his girlfriends is so apparent you can feel it through the page. Of course, being a harem comedy that proclaims it's going to have 100 girls, it really wants to appeal to as many waifu tropes as possible. Which leads me to the, uh, lolis. So far, there's been 3 lolis, 5 if you count Kurumi and Momi. There are also 3 (technically 4) adults in the situation, one of whom is the director of the school (not to mention the mother of one of the girls), which is a, uh, skeevy sounding situation to those who aren't used to the usual anime tropes. But if you can look past those (or are already desensitized to the usual anime/manga skeeviness) I truly think you should give 100kanojo a try.
Mairimashita! Iruma-kun
robin my love <3 Ahem. Sorry. Got something stuck in my throat there. On a more serious note, the best way I can describe 'Mairimashita! Iruma-kun' is 'Poor MC gets caught up in something bigger than him, but he improves and achieves friendship in doing so.' The manga follows a similar structure to the classic action trope of growing in levels, but it also has a focus on the rest of the cast. While it is less so than Iruma himself (he is the title character, after all) I can say with certainty that this manga has made me fall in love with each and every misfit in Iruma's class, as well as every other character Iruma encounters. It's just a feel-good manga for people looking to feel good.
Please don't bully me, Nagatoro
Nagatoro and Sen make for an unorthodox couple, but how they push themselves to be better and the growth their characters go through is wonderful to read. It starts out rocky, but if you enjoy seeing people strive to become better for their loved ones I believe Nagatoro is the manga for you. It also has plenty of Slice-of-Life tropes one can enjoy, and the comedy isn't half-bad either.
Yancha Gal no Anjo-san
With the anime adaptation of Nagatoro-san, bully girls have become more popular as of late. While I wouldn't say Anjou necessarily fits the sort of 'step on me ma'am' trope most people are looking for, the main couple is absolutely adorable. Where Nagatoro is a little rougher, Anjou is more teasing and soft. Her relationship with Seto is so fucking wholesome, and they both seem to genuinely enjoy each other's company. If Nagatoro's more bully-like nature put you off, I believe Anjou's kinder attitude will make for a much nicer read.
Kakegurui Futago
While I've read a few chapters of Kakegurui - Compulsive Gambler, I can say with certainty that Twin has given me a much more enjoyable reading experience. Twin follows Mary (or Meari, if you prefer) when she first starts attending Hyakkaou. Like Yumeko, she makes a strong entrance by beating the class bully. Unlike Yumeko, however, Mary feels like she's actually trying to strategize and win. In general, Mary was much more likable as a main character, and following her journey through Hyakkaou was beyond riveting. If you wanted Kakegurui but less horny, I believe Twin has got you covered. Also, Hoshizuka is for sure gay for Mary.
Oshi no Ko
AHHHHHHH. AHHHHHHHHHHHH!!!!!!! I'll be honest, when I first picked up Oshi no Ko from a video recommendation, I did not expect to be impressed. While I did follow Aka Akasaka's previous work, Kaguya-Sama, I did not think that Oshi no Ko was going to be as riveting as it is. Oh my fucking god, I love this manga so much. The comedy, the drama, the CHARACTERS!!!! I love Aquamarine with all of my fucking heart, and Akane is best girl [but Kana is pretty cool too <3]. I love all of the characters, save for Ruby, who really felt... underutilized. And creepy. And like she's just a plot device to trick one of the love interests into getting closer with Aqua. But honestly? Ruby's character is probably the only one I could call bad. All of the others have my full heart; I just wish Ruby felt like... she belonged in the all-star cast.
Ao no Flag
If you haven't already, read Blue Flags. What began as but a simple man stumbling across a cute tiktok with the tag #blueflag underneath it quickly spiraled into a tale of love and heartbreak and a truly compelling story. Make no mistake: there are no big twists here. There are no sudden changes of heart, no world-ending calamity. This is a story of people. Call them good, call them bad, but at the end of the day, they're just people. Blue Flag is a good romance manga. In fact, I might even go so far as to say it is an EXCELLENT romance manga. It explores and writes its characters extremely well. There is no one I truly 'hate' in this manga, because it goes through the extra effort of making all of them feel real. Everyone, from the side-characters to the love interest to the 'perfect best friend,' are all explored and can all be understood (though sometimes not without some legwork. talkin' bout you, Kensuke and Shingo. Especially you, Kensuke). And that's interesting, isn't it? Because although I may disagree with them at times, a part of my brain acknowledges their opinions as something unique to them, and I somewhat respect it. The author made every character feel like they were alive and breathing, with opinions and thoughts and life experiences, with no two being the exact same. And I adore it. So read Blue Flag. Because it's not often I can say that a manga made me feel truly connected with its story and its characters.
Kanojo mo Kanojo
Though a smaller harem than most, I'd say Girlfriend, Girlfriend is for sure one of the funnier harem comedies I've read. While harem comedies usually rely on misunderstandings for their comedy, GFGF takes the complete opposite approach. All of the three main characters are absolute buffoons, and I adore all of them. The main character Naoya is probably one of the best harem protagonists I've seen. He shares quite a few traits with another fellow harem MC, namely one Rentarou from 100kanojo, and his combined idiocy yet earnest love for both of his girlfriends makes GFGF a much more enjoyable read than most other harem comedies. Also, Saki is definitely bisexual.
Kumo desu ga, nani ka?