Book Influencer Kayla Kleinman & Jeremy’s Bookstore Engagement

Content creator Kayla Kleinman and New York City public school teacher Jeremy Rodriguez are sharing their unique journey to the altar! This beloved couple, recently engaged after a bookstore scavenger hunt proposal that captivated Instagram, shared their story on The Wedding Reporter Podcast. From childhood coincidences to a seriously playful long-term relationship, Kayla and Jeremy offer a refreshing perspective on modern romance and wedding planning.

While Kayla and Jeremy grew up in the same small town north of NYC, attended the same schools, and even shared many teachers, their paths never truly crossed until college. Kayla, a musical theater enthusiast, and Jeremy, a musician, were involved in different aspects of the arts. They even discovered later that they both attended the same ska concert in 2009!

Their real connection sparked at a summer day camp where they both worked as counselors. Kayla, the dance counselor, and Jeremy, supervising fifth-grade boys, found themselves drawn to each other. “There probably wouldn’t have been an avenue for us to like, I wouldn’t even say reconnect, would be like connecting for the first time,” Kayla reflects, “camp absolutely was like the vibe.” Their shared love for fun and a series of opportune early arrivals at movie nights allowed their friendship to blossom into something more. Fast forward 14 years to the summer of 2011, and their long-term relationship officially began.

Jeremy’s proposal to Kayla was a masterclass in personalized romance, meticulously planned to delight his book-loving fiancée. He designed an elaborate bookstore scavenger hunt across New York City, enlisting friends and family as “breadcrumb clues” along the way. Knowing Kayla dislikes big surprises but appreciates a thoughtful lead-up, Jeremy ensured she had an inkling of what was coming.

Kayla, with her keen eye for detail, picked up on subtle clues: Jeremy’s unusually casual demeanor about band practice, her best friend’s persistent invitations, and even her friend suggesting a pre-proposal manicure (unbeknownst to the friend!). The grand finale took place at The Strand Bookstore, a place deeply significant to their relationship. Kayla recounts, “It was very surreal… I just totally blacked out in that moment.” The proposal, captured on video by friends and family, was filled with giddy laughter and overwhelming joy. Jeremy spent over a year planning, navigating countless Google Docs and Excel sheets, and even holding off on inviting out-of-town guests until the ring was in hand.

Now engaged, Kayla and Jeremy are taking a relaxed approach to wedding planning, aiming for Summer 2026. Kayla, a self-proclaimed “summer girly,” envisions getting married while tan and relaxed. As a teacher, Jeremy’s summer availability also makes it the ideal time.

Kayla has already made some non-negotiable declarations, famously shared in a viral video:

The couple is currently venue hunting in the New York area, balancing proximity to both NYC and their hometown. With a large and boisterous family and many friends, they anticipate a guest list of around 250 people, prioritizing a space with ample room for dancing.

Kayla and Jeremy’s advice for other engaged couples? Keep the course and be chill. Jeremy emphasizes mutual understanding and going with the flow. “One person might care more than the other, then that’s just what it is. Like you just go with the flow of all of it,” he advises. Their focus remains on the joy of being surrounded by loved ones, regardless of the venue.

With wedding planning in full swing, Kayla continues to expand her online presence. She recently launched her highly anticipated Summer Reading Guide and is growing her presence on her YouTube channel, in addition to her main platform on Instagram and Substack. Jeremy, enjoying his summer break from teaching, is ready to support Kayla in their exciting next chapter.