Jill Wagner made her mark in Hollywood when she became a regular sketch performer in Ashton Kutcher’s comedy series “Punk’d.” In 2017, “Teen Wolf” alum Wagner married former pro hockey player David Lemanowicz. Just two years later, the couple stated that they were expecting their first child. Their daughter was born in April of 2020 when Wagner was 41 years old.
Motherhood seems to have altered Wagner’s perspective on life. After she welcomed her daughter to the world, she said that she no longer felt her twenties were the best years of her experience. Wagner is confident that her best years are still to come.
Molly Ringwald - 41
80s child star, Molly Ringwald, who got her claim to fame in the movie “The Breakfast Club,” married her second husband, Greek-American writer, and book editor Panio Gianopoulos, in 2007. Together they have three children. The couple’s daughter Mathilda was born in 2003 when Ringwald was still in her thirties.
Getting pregnant again proved to be difficult for Ringwald as she experienced some health issues that needed to be addressed. After having surgery to remove several fibroids, Ringwald was able to get pregnant again. This time she wound up giving birth to twins, Adele and Roman, in 2009 at the age of 41.
Mary Stuart Masterson - 43 & 45
Actress and director Mary Stuart Masterson met her husband actor Jeremy Davidson when they starred together in Cat’s 2004 stage production on a Hot Tin Roof. They were married in 2006 and continued to work together both in front and behind the cameras.
This was her fourth marriage, but we’re guessing the one that brought the most joy since the couple has three kids together. Their son Phineas Bee was born in 2009 when Masterson was 43-years-old. They learned that they were expecting again and announced the pregnancy just 17 months later, to the couple’s surprise-twins Wilder and Clio in 2011 when the actress was 45.
Milla Jovovich - 44
Model-turned-actress Milla Jovovich met her current husband, film writer Paul W. S. Anderson, on "Resident Evil’s" set in 2002. He proposed the following year, but their relationship was on and off for several years after that. Ultimately they reconnected and had their first child in 2007, a daughter named Ever Gabo.
The couple’s second daughter, Dashiel Edan, was born in 2015 while Jovovich was still in her thirties. After experiencing an unfortunate miscarriage, the actress was nervous when she learned that she was pregnant at 43. Even though she spent a lot of time in doctor’s offices waiting on test results, the baby was born happy and healthy. The couple’s third daughter, Osian Lark Elliot, was born in 2020 when Jovovich was 44 years old.
Alanis Morissette - 42 & 45
Singer Alanis Morissette has been known to find inspiration for her music in her dating life. After a failed engagement to Ryan Reynolds, she went on to marry rapper Mario "Souleye" Treadway in 2010. They welcomed a son that same year and named him Ever Imre.
Morissette gave birth to her second child in 2016. Onyx Solace was born just weeks after the singer’s 42 birthday. Their little family wasn’t complete just yet, though. The couple welcomed a third child in 2019. Morissette gave birth to a son, Winter Mercy, at the age of 45! All three of her pregnancies forced her to overcome postpartum depression, which she has been incredibly open about with the public.