‘Saturday Night Live’ Alum Cecily Strong and Fiance Jack’s Relationship Timeline

Cecily Strong and Jack: A Love Story That Blossomed in Unexpected Ways

Cecily Strong, the beloved alumna of Saturday Night Live, has found her happily ever after with her fiancé, Jack. Their love story is a beautiful weave of serendipity, resilience, and joy. The two met at a Christmas party in December 2019, a moment that would kickstart a journey of love and growth. Strong’s agent had encouraged her to approach Jack, a man with a mustache who caught her eye. “I talk to the man with the mustache. He’s very cute,” she wrote in a Vulture essay in April 2020. Despite her social anxiety and the exhaustion of the night, she was drawn to him. After the party, they exchanged numbers and started dating. Three years later, in December 2023, Jack proposed to her in a private and intimate moment. The engagement was revealed in March 2024 during her appearance on Late Night with Seth Meyers. Strong humorously shared how she discovered the news when Jack showed her a text from a friend asking, “How did it go?! Ring emoji.” With that, she knew the answer.

Falling in Love Amid Grief and Growth

The early days of Cecily and Jack’s relationship were not without their challenges. At the time they met, Strong was grieving the loss of her younger cousin, Owen, a death that deeply affected her. In her Vulture essay, she reflected on the emotional landscape of those days. “At first, I thought it was so difficult to meet someone right as I was losing someone I loved so much,” she wrote. Yet, she found solace in Jack’s patience and understanding. She even came to see their relationship as a gift from Owen, a way to continue the love she felt for her cousin even in the midst of sadness. The couple’s bond grew stronger as they navigated these complex emotions together. Jack’s presence became a source of comfort and strength for Strong, and she began to see him as a reminder that love could coexist with loss.

A Private Engagement and the Road to Parenthood

In December 2023, Cecily and Jack took the next step in their relationship when he proposed. True to their low-key nature, the engagement was private, with Strong later sharing the heartwarming story of how she found out. In a humorous twist, she revealed that her engagement ring initially only fit her index finger. “I don’t know my ring size—I wear, like, every size ring,” she shared on Late Night with Seth Meyers. “So, he took one of those, and it was five sizes too big.” Despite the ring’s initial mishap, the couple was overjoyed. A year later, in November 2024, they announced another milestone: Cecily was pregnant with their first child. In an Instagram post, she shared the news with a mix of humor and gratitude. Referencing her past SNL sketch as Goober the Clown, who had an abortion in a storyline, she wrote, “I’m happy to report that same clown is now very happily pregnant from IVF at 40.”

Celebrating Life and Love

As Cecily and Jack prepared for the arrival of their baby, they celebrated in true style. In February 2025, Strong hosted a baby shower, surrounded by friends and family. She took to Instagram to express her gratitude, writing, “Best birthday of my life. Everyone should have a baby shower with the greatest group of friends and family on Earth for their 41st.” She also acknowledged the significance of her journey, noting that she felt “incredibly lucky and grateful” to have the opportunity to become a mother at 41, especially with a supportive partner by her side. The caption ended on a celebratory note: “I think that’s worthy of a proper f—ing celebration!” Shortly after, Strong showcased her baby bump on the red carpet at SNL’s 50th-anniversary special, exuding confidence and joy.

Reflections on Love, Loss, and Motherhood

Cecily Strong’s relationship with Jack has been a journey of growth, marked by moments of grief, love, and new beginnings. From meeting at a Christmas party to navigating the challenges of IVF, their story is a testament to resilience and the power of love. Strong has been open about her experiences, using her platform to share her struggles and triumphs. Her journey into motherhood, in particular, has been a source of pride and reflection. “While it may seem odd at first to have a giant baby shower,” she wrote, “I know how incredibly lucky and grateful I feel to have existed in a time and place where I could make the choice and actually get to safely (knock on wood) become a mom at 41. With a fantastic partner.” Her words highlight the importance of choice, love, and support in her life.

A Legacy of Love and Laughter

Cecily Strong and Jack’s relationship is a reminder that love can bloom in the most unexpected ways. From a chance encounter at a Christmas party to building a life together, their story is one of hope and joy. Strong’s ability to find laughter and light, even in difficult times, has endeared her to fans and made her journey all the more inspiring. As she prepares for motherhood and continues to navigate life’s ups and downs, Cecily Strong remains a beacon of resilience and humor. Her story, shared with grace and vulnerability, is a testament to the power of love to transform and uplift.