The wedding gift tradition – something old, something new, something borrowed, something blue – has no meaning to this list of celebrities. There are a number of reasons these men and women decided to delay or completely avoid heading to the altar. As they say, to each his (or her) own. Brains, beauty, talent, and riches are just some of the possible reasons these 20 celebrities avoid commitment like a bad script. Whatever the reasons, marriage is not on the horizon for them. Some people on the list are older, some younger. You will find that there are some names that are ready to come off of the list! Enjoy your journey through people who are familiar, generally famous, and almost always financially secure.
1. Winona Ryder
The Stranger Things actress was once engaged to Johnny Depp in 1990 and had a dating thing going with Matt Damon that ended in 2000. It’s not that she doesn’t want to get married, but she sees herself as a serial monogamist. One guy at a time for Winona. It seems to definitely hampered her dating life, as Hollywood men prefer their freedom in their younger days. But there’s no playing the field for Ryder, and she has been dating fashion designer Scott Mackinlay Hahn for the last 6 years. Look for her to come off this list in the near future. At 45 years old her possibilities for hearing wedding bells are fading, and after 6 years of dating she hesitates or he bolts, how long will it take for her to recover?
2. John Cusack
Known for keeping a low profile romantically, Cusack has been rumored to have been married to Amanda Peet in the past, but those rumors are false. He has a history of dating starlets such as Minnie Driver and Lili Taylor, but has thus far not taken the next step to the altar. Part of his mystique is likely due to his devotion to TM, or Transcendental Meditation, a meditation system that has grown to a reported 5 million followers. Current interest Lili Taylor and Cusack share similar Midwestern roots, Cusack being from Evanston, Illinois and Taylor from Glencoe, Illinois. They are only one year apart in age, so there is a strong foundation there for a budding romance. If he drops off of the list, you can add it to the list of romances that are star struck.
3. Oprah Winfrey
Oprah makes the list every year because she has the best situation going for her personally. She is wealthy, has had her partner Stedman Graham by her side for the last 25 years, and has no financially good reason to get married. Did you know she once dated John Tesh? But that was ages ago, and Winfrey, now 63, has basically sworn off marriage. But her romantic life has been hit by rumors, everything from her relationship with Graham being a front to cover up her lesbianism, to her and Graham getting secretly married. One unique aspect of Oprah’s life is that she still is pursuing new avenues on cable entertainment, so keeping her reputation consistent in the public’s eyes is essential. At this point in her life, marriage makes less sense than ever in her mind – personally and financially.
4. Matt Dillon
The current situation with Matt Dillon is fluid. The rumors persist that he has found the woman to settle down with in the person of Italian actress Roberta Mastromichele. At 53, he may be looking to settle down given that he has been seen with Roberta over the past 4 years. The most recent sighting has been in Rome where engagement rumors mounted after she was seen in public with a rather large sapphire and diamond ring, standing beside her beau. But Like Cusack, he remains generally quiet and private about his ongoing relationship, making it hard to get to the heart of the matter. But the fact that it can go either way gives those of you who are romantics at heart a reason to be optimistic.
5. Marisa Tomei
At 53, it seems neither dating nor marriage are in her current lifestyle plans. Tomei has repeatedly said she sees no reason for marriage because she believes she can be a complete person without the need to impose marriage on her life. Her last public engagement was to Logan Marshall-Green in 2012, but he moved on and married Diane Gurich, perhaps because of Tomei’s lack of interest in marriage. For men interested in getting married, Tomei does not appear to be a serious candidate for dating. She has not been completely absent from the dating scene, but her public admission for singleness we believe will have her near the top of the never married list for another generation. George Costanza – you never had a chance.
6. Owen Wilson
Owen Wilson’s life can be summed up with simple numbers: 48 years old, more than 50 movies, 11 known romantic relationships, 2 children, and 0 marriages. He has dated the famous and beautiful including Sheryl Crow and Kate Hudson, both who went on to marry other men. He has kept himself busy both working and dating. But as he is on the upside of 48, he may be in the process of discovering that, like George Clooney, he’s not getting any younger and his star is beginning to fade. With two boys who he finds himself being increasingly attached to, finding the right woman is getting more complicated. Tabloids found him walking with one of his sons, Robert Ford, in Santa Monica, California. His current love interest is actress Scarlett Benchley, which he has been with for about a year now. Like many women who are single, he is finding that being committed to raising them on your own is both a challenge to your time and energy resources.
7. Lauren Graham
She turned the big 5-0 this year, and what is not talked about much is her 7 year relationship with Peter Krause. Graham is publicly very happy with the situation. They have not broached the issue of marriage publicly, but as far back as 2010 Graham said she wouldn’t mind being part of a family. As they say about relationships, it takes two, and she seems willing to be patient and enjoy her current relationship status. She sees Krause as someone who simply is easy to be with, so if this situation doesn’t end up in marriage we may find her permanently populating the list of never married celebrities. There is also the possibility of her own reality show, Waiting on Krause, which may be on your local cable station soon.
8. Hugh Grant
After an unlucky 13 year relationship with Elizabeth Hurley that ended in 2000, Hugh Grant has now been seen with his recent younger girlfriend of 4 years, Anna Eberstein, 35. Grant, now 56, seems content to frolic in the streets of London with Anna, being seen together at the Wimbledon tennis tournament and the Golden Globes. Though he has 2 children, his idea of a successful marriage is one that includes affairs with other people. He was once caught having sex with a prostitute. Though Eberstein had been mum about the idea, Grant is likely to be a regular member on this list. Why get married when playing the field is your lifelong commitment?
9. Seth MacFarlane
The question to ask about how a successful and talented MacFarlane can be on this list is why? There have been rumors about him being gay, but his dating history shows an addiction to short term relationships followed by a break up. Being able to make a woman laugh is a great way to break down relationship barriers, but it seems that act gets old sooner than later. Or maybe it was his 2013 Oscar’s joke that is coming back to haunt him: “Congratulations, you five ladies no longer have to pretend to be attracted to Harvey Weinstein.” Bad timing or is this an open revealing of his character? When you have to explain a joke, it always means trouble. Then again, maybe MacFarlane’s comedy routine always is in the “on” position, making it impossible to move to a more serious relationship.
10. Sheryl Crow
Sheryl Crow may be soon dropping off the list of never married celebrities. Some may be thinking, “It’s about time!” but she has her own view of her renewed interest in marriage at 55. People magazine quoted her as saying, “I think I would skip the engagement part [next] time, having been engaged a couple times,” she says. “If I was that close to getting married, I would just go do it.” She has two adopted children and they have played a significant role in her attitude change. Raising 2 children on your own can wear you down pretty quickly, especially after crossing the 50 age boundary. Marriage and children. Who would have thunk?
11. Al Pacino
What does a 77 year old man and a 38 year old woman have in common? Not much, unless you are Al Pacino and the woman has been dating you for more than a decade. They were last seen being playfully romantic on the beaches in Mexico. Stranger things have happened, but after being single 77 years, is there really anything that will change your mind? Besides, he has 3 children from former romances with Jan Tarrant and Beverly D’Angelo. Love may be found in a number of strange places with even stranger people, but marriage is a completely different ball game. To be fair, if you have ever watched an interview with Pacino, you will find he is a much different person than his on screen roles. (He does not yell as nearly as much.)
12. Condoleezza Rice
One of the non-Hollywood celebrities who made the list, the former Secretary of State had one known relationship about 30 years ago with NFL player Rick Upchurch, but hasn’t felt the need for marriage since that failed attempt. But new rumors have sprouted up that she may be getting engaged. Those rumors began as she was seen with her boyfriend shopping for jewelry. She will be 63 in November, and seems to be realizing that she can’t bury herself in her work forever. But having been on your own for a long time, as other celebrities on this list say, it makes changing more difficult, especially when it involves letting another person completely into your life.
13. Drew Carey
Drew Carey may be one of the more unfortunate reasons to make this list – he is not someone who can be trusted with success. Marriage in large part is a measure of relationship success, and after dumping Nicole Jaracz for marriage and family therapist Dr. Amie Nicole Harwick, it seems he is the one who needs therapy. Though the story is they met “by chance” in 2017 at a party, something doesn’t fit quite right. The year he broke off the engagement, 2012, was the same year that marked 5 years as host of The Price is Right. He has a long term contract with the show, and at 59 it is a safe space to be at. Whether or not he wants to share that safe space emotionally and financially remains to be seen, but his past history is a definite red flag.
14. Dana Delany
Maybe all that needs to be said about Delany earning her spot on this list is what she said in an interview: “I do (like relationships), but I have to admit, the older I get, the more I love my solitude, and I don’t wanna give that up.” She added, “A job is often a better bet than many men, and more fulfilling.” She admits that many of her views on men and marriage have their beginnings with her childhood and her parents. The majority of those experiences have had a negative long term effect on her decisions to get married. Though she has dated in the past, at 61 years old it seems she will make a perennial appearance on the list.
15. Jake Gyllenhaal
Of all the relationships Gyllenhaal has been in, the one most often asked about is the one with former girlfriend Taylor Swift. More than 5 years later, he bristles at questions about his former romantic interest. Rumor has it that he is quietly aware of her movements, but the current evidence shows he is happily entangled with Rachel McAdams. McAdams is smart, beautiful, and Canadian, all which are positives for him. Rumors are that he is waiting for Swift’s new album to be released – for reasons unknown. The question is, given Gyllenhaal’s sensitivity to questions about Swift, is it possible we may be seeing one of those once-in-a-lifetime loves, and he will never be able to get over her? If McAdams heads for the door soon, it may speak volumes about the Gyllenhaal-Swift connection.
16. Jane Austen
Connected to Hollywood only through her books being turned into popular romantic movies, Austen is best known for writing Pride and Prejudice. She made the list because it would be her 200th birthday if she were alive, and given the popularity of her books and books that became movies, an honorable mention is in order. She influenced the ideas of love, romance and marriage for almost 200 years, and her books and movies remain a high priority for women of all ages. The irony of her life and writing is that she never got married, yet her most famous works involved marriage relationships. She obviously knew something about marriage that should come naturally to most women.
17. Jamie Foxx
Foxx and ex-wife of Tom Cruise, Katie Holmes, have been heating up the tabloids of late. One item worth noting is that Foxx and Cruise are friends. Another is that Holmes and Foxx have been dating for some time. The two were seen in Paris, May 12, where they were sharing a hotel room together. Last month Foxx publicly admitted the two are now an item – after 4 years! Katie Holmes, even according to Cruise, is very much marriage material. Foxx is 47, and given the length of time it took to come clean about the relationship, we may have to remove him from the list in 2018.
18. Sarah Silverman
Though currently dating actor Michael Sheen, Silverman has long been known for her opposition to traditional marriage. She once tweeted, “I will never get married …Why would I want the govt involved in my love life? Ew. It’s barbaric.” Silverman and Sheen both work to be politically active, and Sheen’s move back to England doesn’t faze Silverman one bit. She told ex-boyfriend Jimmy Kimmel that, “You know me, I’m a loner, so it’s okay.” Being a loner is one sure way to stay unmarried for life. There will always be a spot for you here Sarah.
19. Bill Maher
Maher, who has passed the 60 year mark, has publicly stated he has no interest in marriage – now or ever. His position is part political, part anti-religion. He often speaks about the freedom he has as a single person, though he does admit it is sometimes hard to find a male friend just to go out and do things with. Marriage, in his mind, is more of a restriction to a free life than it is to seeing life through a different lens. While he admits he could have gotten married – and still can – he swears he has no interest in it. Another comedian who has made the list, which makes one wonder if comedy is a committed path to singleness for life.
20. Mary Louise Parker
If you are puzzled that Parker made this list, you shouldn’t be. Though she has two children who she is very committed to, she has never been married. Even an interview with The New York Times had to be corrected to clear up any perception its readers might have had about her having ever been married. For many women, their close, positive relationship with their father is something that cannot be replaced. In one of her books, Dear Mr. You, she reflects on the many men who have passed through her life. Her father will be irreplaceable, and no man can expect to measure up. So that is our list. A few things worth mentioning. If you have seen these same names appear again and again, it is because the number of celebrities, both men and women, who are not willing to at least try marriage seems to be shrinking. Many of the names on this list are celebrities who are close to or have passed 50 years of age. George Clooney, a man you would have expected to be on this list for the next 20 years, got married. So the list may actually have even more repeated names in future years. It may be ironical, but the explosion of social media may be the reason people are willing to give marriage a chance. Talking to virtual images and digital voices every day can get you to rethink what is so great about living alone.