Sean Penn and Madonna kissing in Shanghai Surprise Poster 1987

MOST HEARTBREAKING, TALKED-ABOUT BREAK-UPS AND MAKE-UPS OF THE 80S

by Jane Duncan, freelance writer

January 27 2021

Most people can remember where they were when defining world events occurred, but when it comes to emotional impact for those who grew up in the 80s, the real question is - where were you when Emilio Estevez and Demi Moore broke up and cancelled their December ‘86 nuptials? The world can be cruel when you ship a couple that decides to call it quits, leaving you to wonder if true love really does exist. If you are ready to relive the glory and tragedy of it all, these are some of the most dramatic breakups from the 80s.

The world can be cruel when you ship a couple that decides to call it quits, leaving you to wonder if true love really does exist. If you are ready to relive the glory and tragedy of it all, these are some of the most dramatic breakups from the 80s.

Rob Lowe and Melissa Gilbert

Sodapop, how could you have left your Sandy after declaring your undying love? OK, so this was real life and not The Outsiders, but Melissa Gilbert and Rob Lowe seemed like the ultimate odd couple that somehow seemed to represent true love. Melissa, who came to prominence in Little House on the Prairie, was America’s sweetheart, while Rob Lowe was the ‘not-so-bad boy’ that every singleton wanted to date.
Although they dated for several years, they broke up in 1988, a year after he proposed to her. The reason? He wasn’t ready to ‘settle down’, and she wanted marriage and a family. She continued to pine for and dream about her former lover, who was known to have a roving eye. 
Interestingly, people are said to dream about exes when they lack closure or they are disappointed by reality - two situations that gripped Gilbert for a few months. Of course, he would eventually leave her heart (and her dreams) as she grew from disappointment and made a new life for herself.
Today, Gilbert realizes that breaking up was the right thing to do - especially now that she has sons in their 20s. She says that the pain she went through allowed her to be where she is now - at peace, and happily married to a man she “is absolutely crazy about.”
Melissa Gilbert as Laura Inglis (with dog Jack) in Little House on the Prairie in 1975

Melissa Gilbert as Laura Ingalls (with Jack) in Little House on the Prairie (1975) - public domain image

Madonna and Sean Penn

They were the ultimate badass couple of the 80s - the rebellious boy and girl who proved that real life can tame even the wildest spirit (except the bliss didn’t last long). The couple broke up and made up several times, and their relationship was tainted by reports of volatility - leading the press to refer to them as the ‘Poison Penns’. They filed for divorce in 1989 after their three-year marriage, but Madonna always referred to Penn as “the love of her life.”

Thankfully, fans will always have Shanghai Surprise - a poorly reviewed film that is still magical to those who wish that the pop diva and Oscar-winning actor had never parted ways.

Drew Barrymore and Corey Feldman

Drew Barrymore is the ultimate likable celeb. Recently, she has been wowing audiences on her YouTube channel, which features interviews with celebrities, tips, and of course, talks about the actress’s many life experiences.

Of the many people that have crossed her path, one that is unforgettable for 80s buffs is Corey Feldman - her Oscars date in 1988. They dated for a few months but were torn apart by Feldman’s drug issues. Drew, who had experienced addiction herself (having been in rehab for the first time at the age of 12) was unable to sustain the relationship for her own sake. It had taken blood, sweat and tears to leave her addictions behind, and she had to say goodbye to a guy known for his charm, sweetness, and good heart.

Today, both seem to be thriving in their own way, with Feldman recently hosting a screening of his new documentary on sexual abuse in Hollywood.

Couples from the 80s had a certain glam and secrecy that fans were extremely attracted to in the pre-Internet days. Couples like Melissa and Rob, Madonna and Sean, and Drew and Corey, showed how vulnerable many of these relationships were, owing to the pressures of success in the entertainment industry. Thankfully, many couples (think Demi and Emilio, or Madonna and Sean) have left their shippers with great films that make great viewing on lazy Sundays.

Why Dating in the 80's Was The Best

Drew Barrymore Corey Feldman (cropped)