The Wedding Date Books in Order

At the heart of The Wedding Date series is a loose circle of friends, siblings, and colleagues who keep crossing paths in modern California, and sometimes far beyond. Each novel follows a new couple, but the books are connected through cameos, shared weddings and holidays, and an ongoing sense of community. You can dip in anywhere, yet reading in order lets you watch relationships and careers evolve across the whole cast.

It all starts in The Wedding Date, when Alexa Monroe and Drew Nichols get stuck in a hotel elevator and agree to fake date their way through his ex's wedding. A weekend of pretending turns into a long-distance relationship between a Berkeley political staffer and a Los Angeles pediatric surgeon. The book sets the tone for the series, mixing sharp banter, food-filled dates, and thoughtful conversations about race, privilege, and what it means to show up for someone.

The Proposal shifts the focus to freelance writer Nikole Paterson, who very publicly turns down a surprise scoreboard proposal at a Dodgers game. When handsome doctor Carlos Ibarra helps her escape the cameras and the viral fallout, their rebound fling slowly becomes something neither expected. It is a story about social media pressure, boundaries, and learning to trust that a partner really sees you.

In The Wedding Party and Royal Holiday, the world widens around Alexa. Stylist Maddie and policy advisor Theo, who initially cannot stand one another, find themselves thrown together in Alexa and Drew's wedding plans and discover that their supposed dislike hides real chemistry. Later, Maddie's mother, social worker Vivian Forest, travels with her to England for a Christmas styling job and falls for Malcolm Hudson, a royal private secretary, in a cozy, mature holiday romance that proves love stories do not have an age limit.

Party of Two follows Olivia Monroe, a driven lawyer opening her own firm in Los Angeles, and Max Powell, the junior senator she accidentally flirts with at a hotel bar. Their secret relationship collides with public scrutiny, forcing them to balance ambition, interracial romance, and the cost of life in the spotlight. While We Were Dating returns to the Stephens family as ad man Ben works with rising movie star Anna Gardiner; a late-night road trip for a family emergency leads to real intimacy, a fake relationship for the cameras, and an honest look at anxiety and mental health.

Across the series, Jasmine Guillory writes about Black professionals who love their work, lean on their friends, and negotiate boundaries and consent as carefully as they trade flirtatious texts. The result feels like spending time with a lively, ever-expanding friend group in which anyone might stumble into a meet-cute. Whether you start with the elevator, the ballpark, or the royal holiday, these connected standalones reward both first-time readers and long-time fans.