Brett and Herbert’s courtship grows from a reluctant blind date into a relationship that offers Brett a new measure of attentiveness, warmth, and possibility. It begins at a moment when the life-list deadline has made love one of several urgent, difficult goals, and when Brett’s earlier relationship with Andrew has taught her how fear of being alone can shape her choices. Herbert’s interest does not resolve those pressures, but it gives Brett a relationship against which she can recognize what she wants—and what she had accepted before.

Background and Stakes

The life list gives the romance a practical urgency. Brett must complete at least one goal by the end of the month, and the entire list by September 13 of the following year. As March approaches, she is only halfway through the ten goals; falling in love, having a baby, buying a horse, and getting a beautiful house remain unfinished. She believes that several of these aims are largely outside her control, so romance is at once a desire and a deadline-shaped uncertainty.

That pressure sits alongside a more personal fear. Brett has recognized that she gave up dreams partly because she did not want to be alone. At thirty-four, she regards leaving Andrew as a gamble that could undo what she has worked for. Later, after the decision to pursue the life list has made a different lifestyle unavoidable, Andrew is cold toward her, and she is relieved to have the loft to herself. This context matters to the new courtship: Brett is not approaching love as a simple prize on a checklist, but from the aftermath of a relationship in which her own needs and aspirations have been difficult to defend.

The Introduction

Jay Bohlinger and Shelley bring the possibility of Herbert to Brett during a visit. Jay has recently come in from a run, and the three sit at the kitchen table, drinking tea and laughing. Shelley explains that Herbert is a new professor in Jay’s department, recruited from Penn, and that he has not made many friends in Chicago. Jay adds that Herbert is an expert on the Byzantine conquest of Bulgaria. The proposed dinner is an effort to introduce the newcomer to someone; to Brett, the prospect of a blind date with an academic initially sounds distinctly unappealing.

Brett first declines, and Shelley asks whether she is dating someone. The resistance makes her eventual willingness a choice rather than an instant surrender to her family’s matchmaking. When the dinner arrives, Brett dresses carefully in a black skirt and tights, a close-fitting sweater, and black heels. She jokes to Jay that all this effort is for a man named Herbert and that the meal had better be good. Then she turns as footsteps approach and sees Herbert in the foyer. His appearance immediately overturns her low expectations: the man Shelley and Jay had described as a pedantic scholar makes a striking first impression, and Brett’s thoughts of another attractive man she had noticed disappear.

From Dinner to Courtship

The first evening gives the attraction room to become more than appearance. Herbert’s pedantry is conspicuous: he corrects the distinction between an idiot and a moron, leaving Brett, Jay, and Shelley speechless until Jay laughs and calls him a repugnant pedant. The episode exposes a manner that could easily irritate, but the company does not turn it into a rupture. After midnight, Herbert walks Brett to her car. They agree that the evening was fun, and he asks to see her again.

The next three weeks establish a quickening pattern. Brett and Herbert have the Wednesday dinner they planned, followed by dozens of phone calls and six additional dates, each more interesting to Brett than the one before. She notices small, recurring acts of attention: when she tells a funny story, the corners of his mouth curl before she reaches the punch line; he makes sure that his call to her is the last one he makes at night. These details give the relationship its texture. The courtship advances not through a dramatic declaration but through repeated evidence that Herbert listens, enjoys her company, and wants her close in the ordinary spaces of his day.

His imperfections remain visible. Herbert introduces himself as Doctor Moyer even when a waitress or maître d’ has no need to know his title, and he does not correct people who assume he is a medical doctor rather than a historian with a doctoral degree. Brett finds this manner quirky and sometimes nearly derailing. Yet she has also told Megan and Shelley that life is imperfect and that people sometimes need to compromise. By her judgment, Herbert is not a reluctant compromise in any objective sense; he is an exceptionally desirable partner whose habits she must nevertheless learn to see in proportion.

Intimacy and Contrast

A conversation beneath the stars brings the difference between Herbert and Andrew into focus. Herbert speaks of his growing fondness for Brett and jokes that nerds make excellent marriage material. Brett teases him for his old-fashioned phrasing, and he answers with humor rather than taking offense. She presses closer and tells him she thinks she will like nerd dating, meaning it. Their exchange makes room for Herbert’s awkwardness without requiring him to conceal it, while Brett’s teasing becomes part of their growing ease.

The mention of marriage carries particular weight because Brett had spent four years unable to get Andrew to utter the word. Herbert, after only six dates, is already willing to gesture toward marriage as a real possibility. The contrast is not simply between an unpolished new suitor and a former boyfriend: it measures how different kinds of commitment sound and feel to Brett. Herbert’s directness offers a future that had been withheld in her previous relationship, although the life-list deadline and her fear of making the wrong choice continue to complicate what she hopes for.

A Relationship That Continues

The courtship is not confined to its first dates. By the time Austin comes home from the hospital on Sunday, May 6, Herbert is deeply involved in Brett’s life. He fiercely argues that Brett and the baby should move back to the Astor Street house, but Brett refuses. She says Pilsen is home for now, and that leaving would hurt Selina and Blanca, who have spent the previous month admiring Austin’s photographs and buying her small sneakers and stuffed animals. Brett’s decision establishes that Herbert’s wishes do not determine where she and the baby belong.

Herbert accompanies them home from the hospital, taking photographs through the hallway and into the car. He and Brett laugh while trying to secure Austin in her car seat, and Herbert asks whether it is the right size. The scene gives the earlier courtship a consequential continuation: the man first introduced over dinner is now present in the practical, uncertain work of bringing home a premature infant. Their developing relationship thus moves from flirtation and phone calls toward shared care, while Brett’s attachment to her own home and community remains a boundary she is prepared to defend.