Dan Covey's Proposal to Trina Rothschild
Always and Forever, Lara JeanDan Covey’s proposal to Trina Rothschild is both a declaration of renewed love and a turning point in the Covey family: a choice made between two adults becomes a shared occasion that brings Dan’s daughters into the making of their new family. Planned around Margot’s return and staged beside a waterfall, the proposal culminates in Trina’s joyful acceptance and the family emerging from its hiding places to celebrate.
Causes and Family Context
By the time Dan raises marriage, he and Trina have been a couple since the previous September. Their relationship has grown through proximity and ordinary shared life: they are neighbors, spend time together, and have settled into a rhythm of dinners, outings, hiking, and watching the sunrise. Trina joins the family at the kitchen table several times a week; her laugh and glass of white wine beside Dan’s beer have become familiar enough that her absence feels conspicuous. Lara Jean sees the relationship’s effect on her father: he goes out more and seems energized, and she recognizes that he had been lonely during the eight years since her mother died.
The proposal also follows an explicit effort to include Dan’s daughters in a change that will affect their household. On a rainy evening, while the family eats pizza in the living room, Dan clears his throat and tells them he would like to ask Trina to marry him. Kitty responds with exuberance, but Dan watches Margot with particular hope and nervousness. Her initially blank expression makes her approval uncertain; when she says she thinks the idea is fantastic, Dan checks that she means it. Her response matters not as a formality but as evidence that he wants his daughters’ feelings acknowledged before he makes the commitment.
Dan says he has no ring yet because he wanted to talk with the girls first. He also wants all three daughters present for the proposal, so he plans to wait until Margot returns for the summer. Kitty thinks that is too long to wait, and Margot agrees. The decision to move the proposal earlier preserves the family’s central condition—being together for the moment—while making room for the daughters’ impatience and excitement.
Planning the Proposal
The family settles on a Saturday hike, with Dan intending to propose beside one of his and Trina’s favorite waterfalls. Lara Jean, Kitty, and Peter are to hide among the trees, film the proposal, and then appear with a romantic picnic basket. The plan gives the daughters a role in the occasion without making them the ones who ask the question. Kitty repeatedly argues for recording it in Margot’s name, though Lara Jean suspects that Kitty is also eager to witness the scene herself. Dan, meanwhile, worries about having the video running if Trina says no, and asks them to stop filming if the answer does not look likely to be yes.
The arrangements reveal the difference between Dan’s nervousness and the daughters’ confidence. Before he picks Trina up, he checks again that the camera will be stopped if necessary. Lara Jean answers that Trina will say yes. The family is not simply preparing a surprise: it is preparing to preserve a moment whose outcome Dan cannot control, while the daughters’ certainty makes his risk feel shared.
They arrive early, at Kitty’s insistence, and choose places from which they can see the waterfall without being spotted. Peter holds the phone because Lara Jean judges that he is less emotionally invested in the moment and will have a steadier hand than Kitty. This small practical decision puts Peter in the role of witness and recorder, while the sisters remain close enough to share the proposal directly.
The Proposal at the Waterfall
Dan and Trina reach the waterfall just after noon. Trina laughs as they walk, while Dan laughs in a conspicuously nervous way. She admires the view, unaware that the daughters and Peter are watching from the trees. The waterfall is loud enough that Kitty whispers she can barely hear anything; Lara Jean tells her to be quiet. The scene’s family audience is physically present but temporarily hidden, turning the ordinary hike into a private declaration watched by the people who will share its consequences.
Dan appears to be taking a long time to find what he needs, and Lara Jean briefly fears that he has lost either the ring or his nerve. Then he kneels. She grabs Kitty’s hand; Kitty’s eyes shine, and Lara Jean feels overwhelmed by the moment. Dan tells Trina he had not expected to fall in love again. He thought he had already had his chance and was content because he had his girls, without realizing anything was missing until Trina came into his life. His proposal therefore acknowledges both his love for his daughters and the new love that has changed his understanding of what his life could hold.
Trina’s first response is interrupted by a coughing fit. When it subsides, she asks whether Dan was asking her to marry him. He says he was trying to, and checks whether she is all right. Her answer is an emphatic yes to marriage; Dan reaches for her and they kiss. The brief interruption makes the exchange less like a perfectly controlled romantic performance than a real, slightly unruly family memory. Lara Jean whispers that the moment feels private, while Kitty answers that it is all part of the show.
The Family’s Response and Significance
Trina eventually looks toward the trees. The watchers duck out of sight, but Dan calls them out once she has said yes. They run to the couple: Kitty launches herself into Trina’s arms, and the two tumble onto the grass laughing; Lara Jean hugs Dan, while Peter continues filming. Asked whether he is happy, Dan nods with tears in his eyes and hugs his daughter more tightly. The children’s arrival does not replace the couple’s moment; it completes the planned transition from an intimate proposal to a family celebration.
The proposal’s decisive consequence is captured in Lara Jean’s recognition that their family has grown. Earlier, Trina’s regular place at dinner had already begun to feel like part of home; the engagement gives that evolving closeness a public promise and a shared memory. The waterfall, the hidden audience, Peter’s recording, and Kitty’s joyful leap all belong to the same change: Dan and Trina choose one another, and the daughters are present not merely to observe that choice but to welcome its place in their family.

