Brett and Herbert begin dating

Brett and Herbert begin dating through a setup arranged by Shelley and Jay, turning Brett’s resistance to another blind date into a new romantic possibility. Their first encounter leads to a second date, a run of calls and dinners, and a growing intimacy that feels notably different from Brett’s long relationship with Andrew: Herbert speaks openly about marriage, while Brett discovers that she can enjoy his awkwardness rather than treating it as a reason to withdraw.

Background and Introduction

By the time Shelley and Jay propose introducing Brett to Herbert Moyer, Brett’s life has been reshaped by her mother’s list of goals. She has a year from September 13 to complete the list, and by the approach of March she is nearly halfway to the deadline with only five of ten goals done. Falling in love, having a baby, buying a horse, and finding a beautiful house remain unfinished; Brett regards most of them as matters she cannot simply control. Her uncertainty about love is sharpened by her age and fear of being alone, which had made leaving Andrew seem like a gamble with the life she had built.

The suggestion comes while Brett is visiting Shelley and Jay. Shelley explains that Herbert is a new colleague in Jay’s department, a professor recruited from Penn and an expert on the Byzantine conquest of Bulgaria. He has not made many friends in Chicago, so they propose having him and Brett over for dinner. Brett initially refuses, comparing the prospect of a blind date with a Byzantine specialist to the social life Shelley dislikes. When Shelley asks whether she is already dating someone, Brett considers her recent romantic history: one false alarm with Brad and no actual dates since her breakup with Andrew. The introduction is therefore not the continuation of another courtship; it is the first concrete opening after a stretch of romantic inactivity.

The First Meeting and First Date

Brett arrives at the dinner dressed in a black skirt and tights, a fitted sweater, and black pumps. She jokes to Jay that she has made all this effort for a man named Herbert and hopes the dinner will be good. Her mock reluctance ends when Herbert appears in the foyer: Brett is immediately struck by him, and thoughts of the Burberry-clad man she had noticed elsewhere disappear. The change is abrupt. The evening she had approached as an obligation becomes a meeting that catches her attention.

After dinner, Herbert walks Brett to her car. He says he would like to see her again and asks if she is free the following week. Brett waits for the dramatic rush she had expected, but her heart keeps its ordinary rhythm; she nevertheless agrees to Wednesday night. That measured response matters to the beginning of the relationship: attraction is present, but it does not arrive as a sudden certainty or erase Brett’s caution. She accepts the next date without pretending to feel more than she does.

Courtship and Compatibility

The next three weeks turn that first invitation into a sustained courtship. Brett and Herbert have their planned Wednesday dinner, followed by dozens of phone calls and six further dates. Each meeting is more interesting to Brett than the last. She notices affectionate habits rather than only grand romantic gestures: when she tells a funny story, the corners of Herbert’s mouth lift before she reaches the punch line, and he makes her his final telephone call so she is the last person he speaks to before sleep.

Her interest is not uncritical. Herbert repeatedly introduces himself by his academic title, even to people who do not need to know it, and lets others mistake his history doctorate for a medical degree without correcting them. These small mannerisms nearly derail Brett, who remembers having told Shelley and Megan that life is imperfect and that people must compromise. She recognizes that Herbert is not a compromise in the sense of an inadequate choice, even though his quirks test her patience; in her assessment, he is an exceptionally good prospect.

Their exchange about dating makes the difference between Herbert and Andrew especially clear. When Herbert says he is growing fond of Brett, she laughs at the old-fashioned phrasing. He takes her teasing in good humor, calls himself unhip, and presents nerds as smart, successful, faithful, and good marriage material. Brett recalls that Andrew would not say the word marriage during their four years together, whereas Herbert is already raising the possibility after only six dates. She moves closer to him and says she thinks she will like nerd dating, meaning it. The moment joins humor to a serious contrast: Herbert’s directness offers the prospect of commitment that Brett had not received from Andrew.

Development and Later Consequences

The early relationship continues alongside Brett’s other obligations. As she prepares to travel to Seattle, Herbert says he will miss her and that he is growing fond of her. Their affection has become reciprocal enough for him to express attachment plainly, while Brett answers with teasing rather than retreat. The exchange reinforces the courtship’s characteristic balance: Herbert is earnest and somewhat formal; Brett is amused by that formality but increasingly comfortable with it.

Later, when Austin comes home from the hospital, Herbert is closely involved in the moment, taking photographs down the hospital hallway and into the car as he and Brett struggle to secure the premature baby in her car seat. He had argued fiercely for Brett and the baby to move back to Astor Street, but Brett refuses: Pilsen is their home for now, and the women there have already welcomed Austin by buying her tiny sneakers and stuffed animals. This later disagreement shows the relationship developing into shared practical decisions without displacing Brett’s own judgment about where she and the baby belong. Herbert’s presence in the return home marks how far the connection begun at Shelley and Jay’s dinner has extended, while Brett’s insistence on staying in Pilsen preserves her independence within it.