Honey and Clover (2005) and related work:
Honey and Clover (2005) IMDb
A group of students at an art college deal with money and other troubles for about a year. One day, a new girl arrives, and two of the guys fall in love with her but are very bad at showing it. The first one starts by taking pictures of her with gnome props, producing an Internet fandom. The second is more shy and tries to befriend the stressed-out girl first. It takes a few episodes worth of road movie for his outlook to change.
Josei romance, comedy, moody coming-of-age. The girl, whose nickname is homonymous with “hug” in Japanese, is a strange character: a moekko whose appearance is either childlike in a biologically improbable fashion (she is 18) or perpetually deformed for the series' comedy, which is sometimes over the top. Since the show seems aimed at women, I assume the character’s designed this way for empathy, but you can read it as pedophilia à la Strawberry Marshmallow (2005).
Occasionally, the series dips into the vein of gilded realism typified by Here Is Greenwood (1991). For example, the main character muses to himself that “It feels like my hit points just dropped to half” on the subject of general depression about the uncertainties of love and growing up. However, theatricality and other bad gags undermine that aspect almost fatally, along with excessive use of poor extradiegetic vocal music.
References here: March Comes in Like a Lion (2016).