Hugh Hefner’s former girlfriend, Kendra Wilkinson, reveals that her relationship with him, which had a 60-year age gap, has caused her issues with intimacy. Celebrity News News Viral Hugh Hefner’s former girlfriend, Kendra Wilkinson, reveals that her relationship with him, which had a 60-year age gap, has caused her issues with intimacy. Author March 23, 2025 Kendra Wilkinson admitted her 60-year age-gap relationship with Hugh Hefner still causes her 'problems' with intimacy. Credit:... Read More Read more about Hugh Hefner’s former girlfriend, Kendra Wilkinson, reveals that her relationship with him, which had a 60-year age gap, has caused her issues with intimacy.