Hugh Hefner girlfriends are beautiful, stylish, and personable. Playboy founder Hugh Hefner is known for having multiple live-in girlfriends at one time. There was even a reality show created about his girlfriends, which gave audiences an inside look at life inside the Playboy mansion. All of Hugh Hefner’s girlfriends on this list were with him long-term, and have been featured in “Playboy” magazine.
- Holly Madison. Born in Astoria, Oregon on December 23, 1979, Holly Madison was Hugh Hefner's number one girlfriend for many years. She attended Portland State University for two years before moving to Los Angeles to attend Loyola Marymount University. She was featured on the television show "The Girls Next Door," which was about the lives of Hugh Hefner's girlfriends. While Holly was his girlfriend, she appeared on the cover of "Playboy," and became a photo editor for the magazine. After her and Hugh Hefner broke up she moved to Las Vegas and headlined Peepshow at the Planet Hollywood Hotel and Casino.
- Crystal Harris. Hugh Hefner's current, and only girlfriend is Crystal Harris. The youngest of two sisters, Crystal Harris grew up in San Diego, CA. She attended San Diego State University and majored in Psychology. She met Hugh Hefner in 2008 at the Playboy's annual Halloween party, and shortly after moved into the mansion. In 2009 she starred on the reality show "The Girls Next Door," and became a Playboy Playmate. Her status as Hugh Hefner's girlfriend switched to fiancee when he proposed in 2010.
- Kendra Wilkinson. Born in 1985, she was one of Hugh Hefner's girlfriends that was featured on the reality show "The Girls Next Door." She grew up without her father, and was raised by her mother and grandmother. She met Hugh Hefner at his 78th birthday party, where she was hired to be one of the "painted ladies." Shortly after that encounter she moved into the Playboy Mansion and became Hugh Hefner's girlfriend. She broke up with Hef to began a relationship with pro-football player Hank Baskett. She married and had a son with Baskett, which was documented in her own reality television show, “Kendra.”
- Bridget Marquardt. Born Bridget Sandmeier in 1973, she grew up in California. She has an Associate Degree, a B.A. in communications, and a Master's Degree in Communications. Around 2001 she became a regular guest at the Playboy Mansion, and in 2002 she moved in and became one of Hugh Hefner's girlfriends. She was a part of the reality show "The Girls Next Door" along with Hef's other girlfriends at the time, Holly Madison and Kendra Wilkinson. She graced the cover of "Playboy" magazine three times, which is something she strived to do prior to becoming Hef’s girlfriend. Bridget and Hef broke up in 2008, and she began dating and moved in with director Nicholas Carpenter.
- Barbi Benton. Another well known former girlfriend of Hugh Hefner is Barbi Benton. She was born Barbara Klein on January 28, 1959 in Sacramento, California. She grew up in Sacramento, and at the age of 16 moved to Los Angeles to try and break into the entertainment industry. She became Hugh Hefner's girlfriend in 1968, and moved into the Playboy Mansion. She appeared in and on the cover of "Playboy" magazine. Benton left Hef because she wanted a family, and he did not. She married George Gradow and 1979, and together they have a son and daughter. She has appeared in a number of "The Girls Next Door" episodes, one of which Hef, Holly, Kendra, and Bridget visit Barbi and her family.