Adam Sandler, the American comedy hero, is gaining all the light because of his latest offering, Happy Gilmore 2. His family has been in the limelight for the same reason. Adam is best known for his roles in The Wedding Singer, Happy Gilmore, and Uncut Gems and has been a beloved comedy superstar in the Hollywood industry. On one hand, his professional life talks about his larger-than-life comedy roles, his personal life is rooted in privacy, loyalty and also stability. Most of his fans know him to be a dedicated husband to Jacqueline, a.k.a Jackie Sandler.
Although before Adam settled down with Jackie, he was rumoured to be in relationships with many women whose histories have been less known. There have been a few lucky women who reportedly dated Adam. It was in the early 1990s that Adam gained fame as a cast member of Saturday Night Live. Despite being one of the most well-known comedy stars during his time, he did not lead a highly prolific dating life during his initial days of success. Reportedly, he was seen bouncing from one relationship to another, and due to the same, his dating life has always been speculative.
Alicia Silverstone’s private relationship with Adam Sandler
It was in the 1990s that there were many Hollywood tabloids and columns that claimed that Adam and Alicia were in a rumoured relationship. Alicia, back then, was one of the actresses who was highly in demand because of her role in Clueless (1995), where she played Cher Horowitz. She reportedly had also worn a Happy Gilmore t-shirt during the 1996 premiere of the movie. Adam and Alicia were seen at a few social events, and fans of the duo started speculating that them being in a relationship.
Neither Adam nor Alicia ever confirmed being in a relationship. However, there was once a discussion on Reddit that Adam and Alicia had a pretty short romance. Alicia reportedly had said that her PR team was adamant in keeping her relationship a secret as they were of the thought that it was not correct for her image. The chapter on the relationship of the duo mostly remains unverified.
Adam Sandler’s short romance with Heather Graham
Back in the 1990s, another name linked with Adam was that of Heather. She has been known for her work in Boogie Nights and Austin Powers: The Spy Who Shagged Me. They never confirmed their relationship, but reportedly, had a brief fling. They were not even seen together at parties. However, Heather’s name has been one of the most well-known ones in Adam’s pre-marriage dating life. Their relationship has been a part of Hollywood’s gossip mill without much substance.

Adam Sandler was loosely linked with Lauren Holly
It was during the late 90s when Adam was linked to Lauren, who is known for her work in Dumb and Dumber. The actress was earlier married to Jim Carrey. There has not been any confirmation about Adam and Lauren being in a steady relationship, but there have been rumours in the mills that both of them may have had a brief romantic relationship.
Was Adam Sandler engaged to Margaret Ruden before he met Jackie Sandler?
Before Adam got married to Jacqueline a.k.a Jackie Sandler, according to a report by Nickswift.com, he was engaged to Margaret, who was his cosmetics company manager. After his relationship with her ended, Adam was then linked to Alicia. When Adam got to know Jackie, she was not a known actress. Adam, in the past, has worked with leading ladies on the big screen, such as Bridgette Wilson, Happy Gilmore fame, Julie Bowen, to name a few. Adam, once before his marriage, had told the Daily Mail about what he thought of the institution. He said:
“The problem with me, as far as getting married and having a family, is that my comedy is so important to me.”
What are your views on Adam Sandler’s past relationships?
Also Read: Meet ‘Resident Alien 4’ Star, Alan Tudyk’s Wife Charissa Barton: Dancer, Helped Him Direct The Show