The Real Heartbreak is the fourteenth episode of season two of The Real O'Neals.
It's Valentine's Day and Kenny has just been dumped. Eileen refuses to celebrate the holiday, as usual.
It's Valentine's Day, and unfortunately for Kenny, he has just been dumped by Brett. Kenny is lying in his bed, suffering from depression, he feels he'll never get over. He contantly listens to It Must Have Been Love (but it's over now), so many times, that it drives the rest of his family insane. Pat and Jimmy, who plan on spending Valentine's Day by going to a dive bar and picking up girls, decide to cheer Kenny up by taking him with them, in hopes that he will find a cute boy to pick up. However, no matter what, Kenny keeps getting reminded of Brett and continues to wade in misery. Women all over the bar become attracted to Kenny's sadness and surround him, coddling him and showing their sympathy. When they hear that Pat and Jimmy are trying to help him feel better, they start to adore them and feel romantically interested in them, giving Pat and Jimmy the idea to use Kenny as a chick magnet. This only works for so long, as they lose track of Kenny and he mysteriously disappears.
- Although this episode is a Valentine's Day themed episode, it aired significantly far after Valentine's Day. This is because there were many episodes, where Kenny was still boyfriends with Brett, that had to air before the events of this episode.
- In season 1, a similar incident happened with "The Real Lent", but since the plotholes weren't as noticeable, the networks didn't bother to avoid this.
- It becomes official that Brett has broken up with Kenny, and this is his final mention.
- Eileen's story is a parody of A Christmas Story.
- Kenny listens to It Must Have Been Love (but it's over now) by Roxette and participates in a parody of the musical number.
- During the musical number, there are a few references to moments in Kenny and Brett's relationship. The sheet projections, show clips from The Real Sin, when Brett showed up in Kenny's room, Brett first becoming Kenny's boyfriend, from The Real Acceptance, Kenny kissing Brett from The Real Confirmation, and Kenny's first kiss with Brett from The Real Christmas. Kenny is seen lying on the inkbed, from The Real Sin. He is also seen, lying down in a church bench, from The Real Christmas. He is also seen at the Rainbow Grind, from many episodes in the series.
- Alison is seen with a girlfriend. Her name is not revealed, but she had a few lines. She was on a date with her at The Rainbow Grind.
- Kenny mentions watching the movie, G.I. Jane.
- One of the servants at The Rainbow Grind fell in love with Pat. Since everyone who works at The Rainbow Grind is someone from the LGBT community, she must be bisexual.
- At the end of the episode, Kenny goes back to the choir room, where he first met Brett in The Real Christmas. He is also heard playing The Greatest Night on the piano, when Pat and Jimmy first walk in.