Dated Khloé Kardashian briefly in 2008, but later regretted making their relationship public, which affected his NBA career.
Married Khloé Kardashian in 2009, but their relationship ended in 2016 due to personal issues and substance abuse struggles.
Married Kim Kardashian in 2011, but their marriage lasted only 72 days.
Dated Khloé in 2015, describing it as one of the most stressful periods due to media attention.
Briefly linked with Khloé Kardashian, but they split before fully disclosing their relationship.
Linked with Kendall Jenner during his time with the Lakers; the relationship faced disapproval from her family.
Dated Kendall Jenner in 2017, drawing significant media attention before they parted ways.
Also dated Kendall Jenner, with their relationship spotlighted heavily in 2018-2019.
Had a tumultuous relationship with Khloé Kardashian, marked by public infidelity and reconciliation.
Dated Kendall Jenner from 2020-2022, with both maintaining a relatively low profile.