The Bachelor’s Vanessa Grimaldi Gives Rare Details on Son Winston
Vanessa Grimaldi's kid deserves a rose for his toddler era.
The Bachelor Nation star provided rare insight into her family life, sharing that her and husband Joshua Wolfe's 2-year-old son Winston hasn't become a troublemaker—yet.
“No terrible two situation yet,” Vanessa told Us Weekly in an interview published April 23. “He’s two and a half, he’s going on three. So, maybe we just completely skipped the stage.”
In fact, the 37-year-old—who welcomed Winston in 2022, one year after tying the knot with Joshua, 40—has enjoyed every part of becoming a mom.
"I love my husband, so in love with him. He’s the greatest human being in the world, but the second I had my son in my arms I was like, ‘I’ve never experienced a love like this in my life,'" Vanessa quipped. "And even now he’s two and a half, he’s able to express himself. He’s able to engage in conversations and reason. He’s witty and he’s a very sweet boy and he gets that from his father.”
That's why The Bachelor alum had trouble separating from her little one in order to attend a string of work events in New York, confessing that she "cried all day" before parting ways.
“It’s a very big deal, but it feels good,” Vanessa continued. “This is my initiation to doing a little bit more Vanessa time away from home.”
As for what makes motherhood so rewarding? Vanessa—who previously got engaged to Nick Viall in 2017, during season 21 of The Bachelor, but called it quits less than a year later—revealed that having a kid has changed her whole perspective on life.
"When the new year hits, you have to take a word," Vanessa said. "Being present was always my word before I had Winston, and now he’s taught me how to be more present in life. It’s such a gift.”
And Winston isn't the only member of her family who holds a special place in her heart. Vanessa is also grateful for her deep connection to Joshua—despite parenthood taking up most of their time these days.
“Luckily, my husband and I really worked on our relationship before having Winston, so we had such a solid foundation,” she explained. “Of course our relationship changed after having a kid. It’s 99 percent of the time focused on the child. But we try to do cute things for each other."
Noting that Joshua recently sent her "flowers, a card and a video," she added, "We try to do date nights whenever we have a babysitter at home and we really try to spend as much time as a family and as a couple to keep that love alive.”
To check in on more Bachelor Nation babies, keep reading.
The Bachelorette, Bachelor in Paradise and The Bachelor alum received his best rose yet when his fianceé gave birth to their daughter River Rose Viall Feb. 2.
Sharing a series of sweet images of their baby girl, the couple wrote, "The best part of life starts now."
The Bachelor season 20 alum, who won season three of Bachelor in Paradise and also competed on the following season of the spinoff in 2017, welcomed her first baby, Rosie, with her husband Jan. 24, 2024. This is her third daughter, as she is also a mom to Kinsley and Charlie from a previous marriage.
The Bachelor in Paradise alums welcomed son Nash Lochland Wendt just before Thanksgiving in Canada. The little one joins brother August.
"Happy Thanksgiving from our now family of 4," Kevin wrote on Instagram Oct. 8. "Everyone meet our son Nash Lochland Wendt 10.7.23. Astrid and baby boy are doing great and ready to come home today. Our new favourite moment in life was watching August meet Nash, smiling the whole time and kissing his new baby brother."
The Bachelor in Paradise couple found paradise in parenthood when they welcomed son Benson Lee Jacobs Kufrin on Sept. 21, 2023.
Nearly eight months after getting engaged at The Bachelor Live On Stage show, the couple welcomed their first child together, a baby boy named Tatum Booth Mock, on Dec. 6, 2022 at 6:13 a.m.
What a gift! The former Bachelor contestant gave birth to son Winston on her 35th birthday on Sept. 29, 2022.
We're not calling it the most dramatic birth story ever, but "in a wild turn of events," shared the finalist from Nick Viall's season, after 90 minutes of pushing, she and her husband of nine months welcomed their honeymoon baby in an emergency C-section Jan. 18, 2022. "What was life before him???" the Arkansas native pondered of 8-pound, 6-ounce Gates Zev Gottschalk. "I can't recall."
But she is certain she and her Bachelor in Paradise love match aren't done building their family. "We'd like two or three," she told Us Weekly. "But Adam has said, you know, we'll see how I do with two and then go from there."
Is this winning? Seventeen months after the Bachelor season 16 victor gave birth to her first child, son Joaquin, in June 2020, she and her husband set an extra seat at their Thanksgiving table for the early arrival of daughter Paloma.
A "small, but mighty" 4 pounds, 15 ounces, their newest addition "is the sweetest girl in the whole-wide-world," she raved on Instagram at the time. "Her smile lights up our days & warms my little mama heart."
Consider Nov. 20, 2021 arrival August the couple's final rose at the end of a long journey. Referencing their cycles of intrauterine insemination and IVF—one of which resulted in an ectopic pregnancy—the Canadian-bred firefighter raved of his bride-to-be, "She is my absolute hero for everything she went through the last 2 days in the hospital, and the last 2 years doing everything it took to get this perfect munchkin."
Their plans for a family actually dated back to some early conversations on 2018's Bachelor in Paradise, she shared on Instagram, and yet "even in my wildest dreams I couldn't have imagined how amazing this would all feel."
Having raced into the world of parenting—welcoming daughter Alessi four months after their January 2019 vows and her little brother and sister in June 2021—the retired driver is ready to pump the brakes.
"I think we're so happy because we have our boy, we have the two girls," the season 22 lead said in 2022 of twins Senna and Lux completing their family. "And I'm already 40, guys. I can't be having kids any later than this in life. I want to be like an active dad. So, I think three is OK."
"Big, Big Plans", they said? On June 8, 2021, Bachelor season 20 final rose recipient and her country singer husband invited all nine pounds of Dutton Walker Lane onto the ranch.
The couple had another run around the rodeo on Oct. 16, 2022, when they welcomed son Baker Weston Lane.
Years after failing to collect a rose in week six of Arie Luyendyk Jr.'s Bachelor season, the health coach grew her own little flower, giving birth to daughter Andara Rose Bowles Mar. 31, 2021 less than a year into her new romance with the San Diego-based entrepreneur.
Though she admitted on pal Scheana Shay's podcast it was "scary" to learn she was pregnant "so soon in a relationship" and while still wed to Bachelor in Paradise love match Chris Randone, she "just knew this was an incredible lesson for me to grow, to lean into love, to have faith in myself and Miles and my future and know that God gives us only what we can handle."
The cutest little stowaway you ever did see. On Feb. 12, 2021, The Road Les Traveled creator and her fiancé invited daughter Nora Blanche Kavanagh along for the ride and she's already proven herself to be a natural adventurer.
"Someone told me not too long ago that traveling with a baby isn't a vacation," The Bachelor and The Bachelor Winter Games alum admitted. "It's a trip. A change of scenery. A relocation of parenting. I feel this in my bones." And yet following jaunts to Hawaii, Miami, New York and Kavanagh's native Australia, "I wouldn't trade a thing if it means I get to show this girl the world."
Three's a crowd? Hardly. Since youngest Reed joined the mix in November 2020, the Bachelor in Paradise OG sweethearts have strongly considered rounding out their family with a fourth.
Tolbert told People he's "10 percent open to the idea," but his bride's baby fever burns much stronger.
Agreed the mom of Emmy and Brooks, "Four would be a great number. They'd have the buddy system! There's just something special about the mother-child bond and I just love it."
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