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After graduation, and a return to her small hometown, Kelsey joins Jessica and Ryan to study for the bar. Kelsey expects that her summer in the big city won’t be the same without Tyler Olsen around. But as Kelsey prepares to join the real world, she discovers that Seattle is smaller than she ever thought.
Kelsey is surrounded by secrets, not only from the clients at her new law firm, but from seemingly everyone else around her. From Jessica to Ryan to her new boss, Bill Simon, everyone seems to be keeping a secret or two. Even Tyler is guarding secrets of his own, but it turns out that there are a few that he’s willing to share.
As her second year of law school begins, Kelsey spends most of her waking hours at the side of billionaire Tyler Olsen’s side. But despite her complete immersion in the Billionaire Boys Club, Tyler’s still resisting asking her out on a date. When a surprise visitor from Kelsey’s past arrives to make amends, will it be the push that Tyler needs? Or will he decide to move on?
Tyler and Kelsey cut their Italian honeymoon short to race back to New York City to be with Tyler’s father, who has been injured in an accident. When they arrive, they quickly discover that their new responsibilities are overwhelming, and the couple tries to make the most of the time they have together. But as family secrets are uncovered and feelings are expressed, Kelsey finds herself allied with the one person she never thought she would be able to understand.
A whirlwind December behind them, Kelsey and Tyler return to their final few months at Darrow Law School. As the couple works to break down the final barriers between them, Kelsey discovers that a surprise storm is brewing, which threatens to destroy everything they've fought for.
It's spring and romance is in the air. Tyler is as attentive as ever, Jeffrey is working hard on Kelsey and Tyler's wedding, and even Lisa Olsen seems to have a new love. But a surprise visit from an old friend turns Kelsey's life upside down and makes her question everything that she thought she knew to be true.
As their final year of law school begins, Kelsey and Tyler go away for a vacation that leads to much more than they expected. When they return to their regular lives, they decide to make some important decisions for their future together. Kelsey learns more than she ever knew about Tyler after they accept a surprise invitation. But an impromptu dinner right before Thanksgiving leads to a confession by Tyler, and a shocking outcome. Will Kelsey be able to make things right?
Finally engaged to Tyler, Kelsey discovers that there is a lot of work in being the fiancee of a billionaire. Between supporting Tyler with his project to change Tactec’s board, and planning a wedding, Kelsey is busier than ever. However, if Kelsey wants to marry Tyler, she’ll need to make time for one more person. Her mother-in-law to be, Lisa Olsen. But dealing with Lisa may be more than Kelsey can handle.
As she heads into her final semester at Darrow Law School, Kelsey runs into a string of bad luck, which Tyler brushes off as accidental. He joins her for a romantic Spring Break, but before it’s time to head back to school, the two of them realize that sometimes bad luck isn’t random at all.
Spending spring break together seems like the perfect milestone in Kelsey and Tyler’s new romance. What could be better than a week in the country followed by another in Kelsey’s former college town? With what seems to be lightning speed, Kelsey and Tyler’s relationship moves from casual dates to talk of marriage. But will Tyler’s insecurities and Kelsey’s hesitation break the two of them apart?