99 Boyfriends of Micah Summers

The titular MC is a 16 year old rich kid who thinks once he finds The One, everything will be hearts and flowers, with magic and extravagant gestures flowing freely. He learns that relationships are not fairy tales, but does he really? (when he realizes he is in love with a different boy, he makes a grand gesture that includes racing towards the train station in a pumpkin carriage.)

I was uncomfortable with the way Micah throws his wealth around (his dad owns a yacht! he can buy his poor friend a fancy air conditioner!), even if his friends do call him out on it several times. The book reads younger; Micah's naivete feels more realistic for age 13 than 16 - but note that there are closed-door references to oral and anal sex.

The author makes a point of saying he needed to write something light and fluffy during the pandemic, so YMMV if When Harry Met Sally is your favorite movie.