A$AP Rocky and Kendall Jenner: A Timeline of Their On-Again, Off-Again Relationship

In the world of celebrity relationships, there's nothing quite like the drama and intrigue of a high-profile romance. For A$AP Rocky and Kendall Jenner, their relationship has been a whirlwind of on-again, off-again dates, secretive meetings, and constant speculation from the media and fans alike. From their first sighting to their most recent breakup, here's a comprehensive timeline of the A$AP Rocky and Kendall Jenner relationship.

From Paparazzi Spotted to Public On-Again

The romance between A$AP Rocky and Kendall Jenner has been a slow-burning fire, with moments of intense heat and periods of frosty calm. The two were first spotted together in May 2015, with paparazzi catching a glimpse of them at a private party in Calabasas, California. However, it wasn't until 2017 that their relationship officially kicked into high gear.

In February 2017, the two were seen together at a ski resort in Colorado, sparking rumors of a budding romance. Over the next few months, they were spotted on several more dates, including a romantic getaway to the Caribbean and a night out at a trendy Los Angeles nightclub.

Kendall Jenner's 2017 Romance Heat-Up

For Kendall Jenner, 2017 was the year of the A$AP Rocky romance. Here are some highlights from their relationship that year:

• In February 2017, the two were spotted skiing together in Colorado.
• In March 2017, they took a romantic getaway to the Caribbean, where they were seen relaxing on a private beach.
• In April 2017, they were seen out and about in Los Angeles, with A$AP Rocky sporting a custom tattoo of Kendall's initials.
• In June 2017, they were spotted at a trendy New York City nightclub, with Kendall looking stunning in a black jumpsuit.
• In July 2017, they took a break from each other, with sources citing their busy schedules as the reason for the separation.

A$AP Rocky's Relationship Red Flags

While A$AP Rocky has been open about his feelings for Kendall Jenner, he's also been linked to several other celebrities, sparking rumors of infidelity and broken promises. Here are some of the red flags in their relationship:

• In 2015, A$AP Rocky was arrested and charged with assault after a physical altercation with a fan in New York City.
• In 2016, he was sued by a model who claimed he had breached a contract with her.
• In 2017, sources reported that A$AP Rocky had been cheating on Kendall Jenner with several other women, including a reality TV star.

The Relationship Downfall: Breakups and Reconciliations

Despite their efforts to make the relationship work, A$AP Rocky and Kendall Jenner ultimately decided to part ways. Here are some of the key events that led to the breakdown of their relationship:

• In April 2018, sources reported that the two had broken up, citing their busy schedules and differing priorities as the reason for the separation.
• However, just a few months later, the two were spotted together at a Los Angeles nightclub, sparking rumors of a reconciliation.
• In May 2018, Kendall Jenner was seen accompanying A$AP Rocky to a Met Gala after-party, further fueling speculation of a reunion.
• In June 2018, the two were spotted on several dates, including a romantic dinner at a Los Angeles restaurant and a night out at a trendy nightclub.

Kendall Jenner's Breakup with A$AP Rocky: The Fallout

When A$AP Rocky and Kendall Jenner finally broke up in April 2018, the two parties faced intense media scrutiny and public backlash. Here are some of the key fallout moments:

• In April 2018, sources reported that A$AP Rocky had proposed to Kendall Jenner, with the two planning a private wedding ceremony.
• However, just a week later, the proposal was called off, with sources citing the couple's busy schedules and differing priorities as the reason for the cancellation.
• In May 2018, Kendall Jenner was seen accompanying A$AP Rocky to a Met Gala after-party, sparking rumors of a reconciliation.
• In June 2018, the two were spotted on several dates, including a romantic dinner at a Los Angeles restaurant and a night out at a trendy nightclub.

A$AP Rocky's Next Moves: A Break from the Spotlight?

Following his breakup with Kendall Jenner, A$AP Rocky took a break from the spotlight, focusing on his music and personal well-being. Here are some of the key developments in his post-breakup life:

• In May 2018, A$AP Rocky released his debut studio album, "Testing," which received widespread critical acclaim.
• In June 2018, he was spotted taking a solo trip to the Hamptons, sparking rumors of a break from the dating world.
• In July 2018, A$AP Rocky collaborated with fashion designer Dapper Dan on a limited-edition clothing line, further solidifying his status as a fashion icon.

A$AP Rocky's 2020 Comeback: The Comeback Kid

After taking a break from the spotlight, A$AP Rocky made a stunning comeback in 2020, re-emerging with a newfound sense of purpose and direction. Here are some of the key developments in his 2020 comeback:

• In January 2020, A$AP Rocky released a new single, "LA Vacation," which featured a laid-back, West Coast vibe.
• In February 2020, he collaborated with fashion brand Versace on a limited-edition clothing line, further solidifying his status as a fashion icon.
• In March 2020, A$AP Rocky was spotted taking a solo trip to the