As of the current chapters of the Spy x Family manga, Loid (Twilight) and Yor have not shared a real, romantic kiss. While there have been teasing moments and near-kisses, including comedic or awkward setups (like in the fake dating scenario or during missions), the story has not yet developed their relationship into a full romantic one with an actual kiss.
The manga tends to focus more on comedy, action, and family dynamics, rather than rushing the romance. However, there is slow development in their emotional connection, and fans continue to anticipate a meaningful romantic moment between them in future chapters.