10 Famous Couples You Forgot Were Once Engaged

10 Famous Couples You Forgot Were Once Engaged

Hollywood romances often burn bright and fast, leaving behind engagements that most people have completely forgotten about. Before the marriages, the breakups, and the new relationships, many of our favorite celebrities were once planning to walk down the aisle with someone entirely different. Some of these pairings might surprise you, while others will make you wonder how you ever forgot they were a thing in the first place!

1. Ryan Reynolds & Alanis Morissette

Before Blake Lively stole his heart, Ryan Reynolds was deeply committed to Canadian singer-songwriter Alanis Morissette. The two got engaged in 2004 after dating for several years, and they seemed like the perfect match. Both Canadian, both talented, and both incredibly likable, they appeared destined for a lifetime together.

However, their engagement ended in 2007, and Morissette channeled her heartbreak into her album Flavors of Entanglement. Reynolds went on to marry Scarlett Johansson briefly before finding his true soulmate in Lively. Morissette also found happiness, marrying rapper Mario “Souleye” Treadway in 2010.

Their split was amicable, and both have spoken kindly about their time together over the years.

2. Kanye West & Alexis Phifer

2006 was a big year for Kanye West and Alexis Phifer—they got engaged! After an on-and-off relationship that started in 2002, Alexis was there for Kanye during some of his defining moments, including the devastating loss of his mom, Donda.

Despite their deep connection, the engagement ended in 2008. West cited the grief from his mother’s death as a major factor in their breakup. Phifer moved on to continue her career in fashion, staying largely out of the spotlight.

West later married Kim Kardashian, but his relationship with Phifer remains an important part of his personal history.

3. Julia Roberts & Kiefer Sutherland

Before the breakups and headlines, Julia Roberts and Kiefer Sutherland were the ultimate golden couple. Flatliners sparks, a June 1991 wedding, and fans losing it over every detail.

However, Roberts called off the wedding just three days before the ceremony, shocking everyone. She left Sutherland for his friend, actor Jason Patric, adding scandal to heartbreak. The breakup was messy and very public, with both parties hurt by the fallout.

Sutherland eventually moved on, and Roberts married cameraman Danny Moder in 2002. Their failed engagement remains one of Hollywood’s most memorable near-misses.

4. Carson Daly & Tara Reid

MTV host Carson Daly and actress Tara Reid were the ultimate early 2000s couple. They got engaged in 2000, representing the peak of pop culture cool at the time. Daly was hosting TRL, and Reid was starring in movies like American Pie, making them a media darling duo.

Their engagement lasted about a year before ending in 2001. The split was reportedly due to their busy schedules and young age. Reid’s partying lifestyle also became more prominent after the breakup, leading to challenges in her career.

Daly went on to host The Voice and married food blogger Siri Pinter in 2015. Reid has continued acting and recently made a comeback in the Sharknado films.

5. Jennifer Lopez & Ben Affleck

From Gigli to engagement headlines, Jennifer Lopez and Ben Affleck were everywhere. Affleck’s pink diamond ring sealed the deal, and Bennifer dominated tabloids between 2002 and 2004.

The couple postponed their 2003 wedding, citing excessive media attention. They officially split in early 2004, leaving fans heartbroken. Both went on to marry other people and have families.

In a twist nobody saw coming, they rekindled their romance in 2021 and finally married in 2022. Their love story proves that sometimes timing is everything, and second chances can lead to happy endings after all.

6. Sheryl Crow & Lance Armstrong

When Sheryl Crow and Lance Armstrong got engaged in 2005, it was a union of two icons at the top of their fields—music and cycling at their finest.

However, their engagement ended after just five months. Crow later revealed that disagreements about having children played a major role in their split. She wanted kids, while Armstrong, who already had three, was hesitant about expanding his family.

Armstrong’s later doping scandal tarnished his reputation significantly. Crow went on to adopt two sons and continues her successful music career, rarely speaking about their relationship publicly.

7. Courtney Love & Edward Norton

Courtney Love and Edward Norton dated in the late 1990s, shortly after Love’s husband Kurt Cobain died. While they were never officially engaged, their relationship was serious and lasted about a year. Norton was rising to fame with films like Fight Club, while Love was fronting the band Hole.

The relationship was reportedly intense but ultimately incompatible due to their different lifestyles. Love was dealing with grief and substance issues, while Norton preferred a more private, stable life. They parted ways around 2000.

Norton has since maintained a very private personal life, marrying producer Shauna Robertson in 2012. Love has continued her music and acting career, remaining a controversial and outspoken figure in entertainment.

8. Demi Moore & Emilio Estevez

Before Ashton Kutcher and Bruce Willis, Demi Moore was engaged to actor Emilio Estevez. They got engaged in 1985 and even starred together in the films St. Elmo’s Fire and Wisdom. As members of the famous Brat Pack, they were young Hollywood royalty.

Their engagement ended in 1986, reportedly due to the pressures of fame and their young ages. Moore quickly moved on, marrying Bruce Willis in 1987 and having three daughters with him. Estevez has been married once and has two children.

Both have had successful careers spanning decades, though Moore’s personal life has remained more in the spotlight. Their engagement is a forgotten piece of 1980s Hollywood history that many younger fans never knew existed.

9. Winona Ryder & Johnny Depp

The ultimate ’90s love story: Winona Ryder and Johnny Depp. Met at the Great Balls of Fire! premiere, engaged in five months, and inked for eternity.

Their three-year engagement ended in 1993, devastating fans who saw them as perfect together. Depp later changed his tattoo to read “Wino Forever.” Both have spoken fondly of each other over the years, with Ryder defending Depp during his legal troubles.

Depp went on to have a long relationship with Vanessa Paradis and later married Amber Heard. Ryder has remained relatively private about her personal life while continuing her successful acting career.

10. Ruby Rose & Phoebe Dahl

Australian actress Ruby Rose was engaged to fashion designer Phoebe Dahl from 2014 to 2015. Dahl is the granddaughter of famous author Roald Dahl, and the couple seemed deeply in love. Rose, who identifies as gender-fluid, was open about their relationship on social media.

The engagement ended in December 2015, with Rose announcing the split on Instagram. She emphasized that they remained friends and that the decision was mutual. The breakup was relatively drama-free compared to other celebrity splits.

Rose went on to star in Orange Is the New Black and Batwoman, becoming a prominent LGBTQ+ icon. Dahl continues her work in fashion, running her ethical clothing brand Faircloth & Supply. Both have moved forward with their careers and personal lives.