In Liar x Liar, main guy normally has it together, but when the female lead breaks up with the main guy. He loses it. Starts crying like a baby and tries to follow her.
(mild spoiler)

Eventually he stops going to school and doesn't leave his apartment.

I found it strangely cute and refreshing. So yeah, I'm feeling mildly sadistic. It's not that often that the guy has a break down instead of the girl.

Since it's awfully specific, guys that have a significant crying time/scenes or fall in to depression due to heroine's actions are also accepted. Groveling or begging the heroine not to leave works too. (Hahaha, I know how this sounds, lol.)

Alternatively, male love interest that uses tears to win the girl is also accepted. (AKA, the emotional manipulator/blackmailer.) An example of this is Oujitachi wa Izonsuru.

Anyways, I'd prefer a non-annoying female lead (but male lead is okay-ish) and no ecchi/yuri/yaoi/hentai/harem (I like yaoi, but I'm looking for a m/f pairing for this theme).

While I would prefer shoujo/josei titles... I'm OKAY with shounen/seinen so long as the guy's not a loser and attractive (Sorry, I'm shallow.). The girl's boobs should not be bigger than a B/C cup (somehow, it's inversely proportional to the story quality and characterization -_-).

Theres the crybaby male lead category [url]http://www.mangaupdates.com/series.html?category=Crybaby+Male+Lead[/url] it's pretty short though
I think a delinquent friend (like 70~90 or so chapters in, sorry) of the MC in oresama teacher does this. He's a recurring side character, and he's not even really a love interest though 🤢
your and my secret i think. Kinda seems to be heading up in a shounen-ai direction

I feel there has to be more, but i cant think of them.

The Circumstances of Our Strange Love

@sunder Thanks for The Circumstances of Our Strange Love. I wish they didn't have so many misunderstandings, but it was a nice story, if a bit shoujo-eque. All it needs is more angst. The ending really caught me off guard.

@lovelylalaland I know the exact character/chapters you're talking about in Oresama Teacher. (I have the particular scenes saved on my computer... lol. He's fav Oresama character, even though he barely appears.) As for Your and My Secret, I've read this a long time ago, but I have a don't recalling any scene like that. Maybe I'll reread it once I get around to it.

Yeah, I'm aware of the crybaby male lead tag, but the majority is BL and there's no guarantee he cries due to the female love interest. I'll probably still go through all them anyways to scratch this itch. Thanks for trying.

Depressed:
Clannad
Dear Mine But he's a child.
Boku no Chikyuu o Mamotte

Begging:
We Are Still...! Manhwa. Ongoing.

Manipulative:
Yoru Made Matenai

Crying miscellaneous (or just can't recall);
Kodomo no Omocha
Bokura ga ita
Otokonoko wa Hachimitsu
Melo Holic

Hwang MiRI does this at times. As much crap as they get (and is often well earned), there are some decent ones that work. Most of the time it's just to "break the haughty".

Hot Blooded Woman Doesn't exactly cry and is somewhat tsundere, but the impact that it has on the main male lead is pretty sad.
Cutie Boy Gets really depressed at times due to the female lead
Love SOS
Apollo no Uta
Kami-sama no Iutoori

I believe this is prevalent in manga by TANEMURA Arina. Takahashi Rumiko might have this once in a blue moon.

I like my men androgynous.
I like my women androgynous.