The engagement of Cecily Strong to her fiancé, Jack, has captured attention as they begin on this new chapter together. Strong first mentioned Jack in a personal essay for Vulture back in 2020, where she shared her journey of discovering love during a profoundly challenging period marked by the loss of her younger cousin, Owen.
In her heartfelt reflections, Strong expressed, “I think you were a gift to me from Owen,” emphasizing the emotional depth of their relationship.
Although she has enjoyed considerable success in her career, Strong remains private about her personal life. However, during a 2024 appearance on Late Night with Seth Meyers, she offered a look into her relationship with Jack. “I got engaged,” she announced with enthusiasm.
Strong’s playful engagement announcement reveals her excitement for the future
Despite an accidental text revealing Jack’s proposal intentions, Strong playfully remarked that she encouraged him to propose “whenever you want to do it, that’ll be the surprise.” Her excitement, however, led her to claim the engagement ring earlier than planned.
“I still then took that from him,” she shared, recounting a difficult night in December when she asked, “Can I just wear the damn ring now?” This spontaneity marked the beginning of their engagement.
In October 2024, Strong shared the joyful news via Instagram that she and Jack are expecting their first child.
Jack’s journey with Strong began at a Christmas party in December 2019, where they were introduced by her new agent. Just days before their respective travels—her trip to California and his to Cuba—they connected in an unforgettable way.
Recounting their initial interaction in her Vulture essay, Strong described feeling socially anxious yet drawn to Jack, noting, “I talk to the man with the mustache. He’s very cute. I have social anxiety, and I’m drunk and tired, so I have no idea what we talk about. He comes home with me.”
The following morning brought more shyness, but Jack took the initiative to ask for her number. Strong humorously recalled giving him the pink-flamingo pen from her psychiatrist to write his contact details, sealing their connection.
Despite her grief over Owen’s passing, Strong acknowledged the complexity of finding love. In her Vulture essay, she reflected on how difficult it was to start a relationship while mourning, stating, “At first I thought it was so difficult to meet someone right as I was losing someone I loved so much.
I knew he’d have to be patient with me. He’d have to let me grieve.” This emotional journey led her to commit to honoring both her love for Owen and her new relationship.
The couple made their public debut at the 2020 SheBelieves Cup in Frisco, Texas, where Strong celebrated the occasion by sharing a video on Instagram featuring her custom U.S. Women’s National Team jersey.
She joyfully remarked, “I spent International Women’s Day watching the best team on earth @uswnt win a soccer game.” Reflecting on their time at the event, she wrote, “He’s excited to be there, to watch women’s soccer with me… Jack is loving the game.”
In December 2023, Strong revealed on Late Night with Seth Meyers that Jack had proposed, but an unfortunate mishap with a text message had spoiled the surprise. Recalling the moment, she said, “One day he was like, ‘I’m so inundated with emails and texts, look at this.’ And the first text was from a friend that said, ‘How did it go?! Ring emoji.’”
Despite the good intentions, the engagement ring presented some logistical issues, as it was much too large for her finger. “I wear like every size ring. So, he took one of those, and it was five sizes too big,” she humorously noted, explaining that she wore it on her index finger out of necessity rather than style.
Now, the couple is eagerly awaiting their first child. In a nod to her earlier SNL skit about Goober the Clown, Strong expressed joy at her pregnancy journey, stating, “I’m happy to report that same clown is now very happily pregnant from IVF at 40.” Additionally, she affectionately referred to her unborn child as “little miss,” hinting that they may be welcoming a daughter.
