Mature Single Women: How Celebs Like Trinny, Jane, and Sharon Thrive Alone

For generations, single women were squeezed into labels like ‘spinster’ or ‘old maid’.

But thanks to the likes of Trinny Woodall, Jane Fonda, Sharon Stone and Linda Evangelista, the script is finally being rewritten.

Today, more women are choosing happiness on their own terms without the need for romance or rings.

While society still loves to ask about settling down or biological clocks, modern single women are too busy thriving to worry about outdated timelines.

In fact, there’s a whole wave of confident women 50 and up who are embracing singlehood as a lifestyle worth celebrating.

The Daily Mail takes a closer look at the mature celebs who choose to stay single.

Trinny Woodall 

Trinny Woodall has long been open about how finding a man is not a priority. 

At 61, she’s single and couldn’t be happier, and wants all women to know, ‘we’re still sexy in our fifties and sixties.’

The Trinny London founder was once married to the late drummer Johnny Elichaoff, with the pair sharing daughter, Lyla. 

She later entered into a relationship with businessman Charles Saatchi, with them parting ways in 2023.

The makeup and skincare mogul has now discovered the ‘joy of not being in a relationship.’

Speaking about being in her single era with Hello!, Trinny explained: ‘I don’t need anyone to complete me.’

She added: ‘Do I want to go to the theatre and not do it on a dating app, but do it through the people I know and their friends? Yes, I do.’

However, she’s fully aware there’s the power of female friendships, admitting that although she can spend time with both sexes.

Despite revealing that she still goes on the occasional date, the beauty said she’d rather spend time with her daughter and people who ‘fascinate’ her.

She told Women’s Health UK’s December issue: ‘The most important thing in life is feeling good, waking up to people I want to see – not sitting through a three-hour dinner thinking, ‘They’re so f****** boring’.

‘If, along the way, I meet someone, great, but my priority isn’t, “I have to date”.’

She continued: ‘When friends ask, “Have you met someone yet?” I go, “No, and I really don’t give a s**t”.’

Tracee Ellis Ross

Tracee Ellis Ross is the internet’s favourite rich, single aunty.

She is now 53, and has never married or had kids – something she has discussed at length over the years.

In 2020, the American actress discussed feeling happily single with NET-A-PORTER’s digital title, PORTER.

She said: ‘I’ve been raised by society to dream of my wedding, but I wish I had been dreaming of my life.’ 

‘There are so many ways to curate happiness, find love and create a family and we don’t talk about them. 

‘It creates so much shame and judgement.’ 

In 2023, she further elaborated on having no children, saying she has had to reexamine what womanhood means now that she is going through perimenopause.

The actress, who is the daughter of singing legend Diana Ross, discussed the changes to her body during her appearance on Glennon Doyle’s ‘We Can Do Hard Things’ podcast, which she co-hosts with her wife, former soccer star Abby Wambach, and sister, Amanda Doyle.

‘I have, for my entire life, been tethered to a very routine cycle. And I’m very connected to my body, so I would know I’m ovulating. I would have all the feelings of knowing that,’ said Ross, who celebrated her milestone birthday on October 29.

‘And all of that is out the window. And I turn 50. And here I am in this open space now, sort of allowing the bubbling up of whatever might be here.’

Perimenopause is the lead-up to the body’s transition to menopause, which is characterised by 12 months without a period. It often begins between the ages of 45 and 55, though can happen much earlier.

Some people may not have any notable symptoms, while others may experience changes in their monthly cycles, hot flashes, trouble sleeping, moodiness and irritability, or depression, according to the National Institute of Health (NIH).

Drew Barrymore

Earlier this year, Drew Barrymore revealed that she is fully embracing her single era after turning 50 in February.

She admitted that she used to chase love, adventure, and excitement, but eventually realised the best relationship she’d ever have was with herself.

The actress wrote in her US Weekly column: ‘I started doing things for me in a way I never had before.’

‘I took myself out on little solo dates. I cooked for myself like I was hosting some fabulous dinner party—candles, music, the whole thing.’

Drew’s dating life has had its ups and downs, and her experience with Raya was no exception.

Back in 2020, she shared on Watch What Happens Live With Andy Cohen that she had high hopes for the app, expecting it to fulfill her dream of a blind date.

Instead, she called it a ‘car wreck’ and revealed she was even stood up by a restaurant owner.

‘Swiping through Raya was like looking through an Us Weekly,’ she joked.

Over the years, Drew has been in several high-profile relationships and has walked down the aisle three times.

She was briefly married to Welsh bartender Jeremy Thomas in 1994 and later to comedian Tom Green from 2001 to 2002.

Her longest marriage was to art consultant Will Kopelman, with whom she tied the knot in 2012.

Though they divorced in 2016, the two have maintained a strong co-parenting relationship for their daughters, Olive and Frankie.

While she’s not ruling out love entirely, Drew has made it clear—her happiness isn’t dependent on romance.

‘If love, in any form, comes along and adds to that? Beautiful. But I refuse to believe that life starts or stops because of anyone else.’

Jane Fonda

Over the years, the famed actress has been involved in a number of very high-profile romances and marriages with record producers, screenwriters and even politicians – but seemingly never managed to find the perfect match.

‘My current and next love are my girlfriends. I’ve had a good run. I’ve closed up shop,’ Jane candidly revealed in a 2018 interview with SiriusXM.

Jane, 87, dated her music producer beau Richard for eight years, until they chose to cut ties in January 2017 after they were reportedly planning an ‘unconventional union.’

The actress was previously married to CNN founder Ted Turner for 10 years, until 2001.

And she also wed politician Tom Hayden in 1973, one year after divorcing film director Roger Vadim, who cast her in the sci fi film Barbarella.

Her children are Vanessa Vadim (from her first marriage), Troy Garity (with her second husband) and Mary Luana Williams (who was unofficially adopted).

Despite her undeniable sex appeal, the star said she has no desire to be in another sexual relationship in 2021.

‘I don’t want to be in a relationship, a sexual relationship, again. I don’t have that desire,’ she told Harper’s Bazaar magazine.

Linda Evangelista

Linda Evangelista has revealed that she is ‘not interested’ in dating again.

The former supermodel, 60, has been a fixture in popular culture since the 1990s.

She has also had some high-profile relationships, including a tumultuous marriage to French former model Gérard Marie, an engagement with Twin Peaks star Kyle MacLachlan and a relationship with billionaire businessman François-Henri Pinault, with whom she shares son, Augie.

However, the Canadian star is currently single, and has expressed no plans to change her relationship status.

When asked about dating in a 2023 interview, Evangelista replied: ‘Not interested. 

‘I don’t want to sleep with anybody any more. I don’t want to hear somebody breathing.’

Linda then stated that her last real relationship ended ‘definitely before the Cool-Sculpting,’ which she underwent from 2015 until 2016. 

Sharon Stone

Sharon Stone is done with dating.

The 67-year-old revealed that she’s no longer seeking out a new romantic relationship and has put that part of her life behind her. 

Appearing virtually on Drew Barrymore’s chat show in 2020, the beauty opened up about how she’s wants to concentrate on other areas of her life.

‘I’m done dating. I’ve had it with dating,’ Sharon told Drew. ‘Because I just find people to be insincere and not worth my time. 

‘I enjoy my alone time and my time with my kids and friends more.

The Emmy winner was previously married to Michael Greenburg from 1984 until their split in 1987. 

She later tied the knot with Phil Bronstein in 1998 but their divorce was finalised six years later in 2004. 

The star is also mum to three adopted sons: Roan, 25, Laird, 20, and Quinn, 19.

Fran Drescher 

Fran Drescher revealed she has a ‘rotation’ of friends with benefits while opening up about her love life.

The 67-year-old actress was previously married to showrunner Peter Marc Jacobson, 67, for over a decade until they got divorced in 1999 and he came out as gay.

‘I have a little rotation,’ she told Page Six at the Cinema Society screening of The Friend in March.

After making the admission, The Nanny star confidently added: ‘I’m Fran Drescher. What do you think?’

Five years ago, she admitted she had a singular friend with benefits she would see a couple times a month.

The Nanny star previously said she will never marry again and plans to grow old with her openly gay ex-husband.

The comedienne said that she still loves her ex and they are ‘very close’ so she chooses to only have a ‘friend with benefits.’

Drescher married Jacobson in 1978 when she was 21, but they separated in 1996 and divorced in 1999.

Despite their split, they remained good friends.

Back in June 2022, she exclusively told DailyMail.com that she and Jacobson are ‘closer than when we were married’ and still love each other, while her ex called her his ‘soulmate.’

‘We are divorced, but still single because it is hard to compete with what we shared. We have been together since we were 15 and we’ve been through so much,’ she explained.

About their bond, Jacobson said: ‘When you are lucky in life and you meet your soulmate, there is nothing that can tear you apart. We vacation together. We do everything together… It is a deep, deep love.’

But he agreed with his ex and said he also wouldn’t marry again.

‘I don’t think there is any reason to get married – it is just a license,’ he said. ‘It is the heart, not a signed piece of paper.’

Teri Hatcher

After celebrating her 55th birthday, Teri Hatcher revealed she was feeling her best being single.

‘There is a difference between being lonely and being alone,’ the Desperate Housewives actress, now 60, told PEOPLE in 2019. 

‘I have been single for a very long time but there is nothing lonely about my life. I want to remove the stigma of that.’

She has been married and divorced twice, first to actor Marcus Leithold from 1988 to 1989 and then to actor Jon Tenney – Emerson’s dad – from 1994 to 2003.