From a window, Maggie sees Mr. Wakem approach and notices that Philip is with him. Philip tips his cap to her, and Maggie runs upstairs, unwilling to spoil a reunion with Philip by the presence of their fathers.
Several days later, Maggie goes out for her usual walk in the rocky area near her house, called the Red Deeps. Maggie's chosen life of deprivation has suited her—she looks stately and older now, though there still remains "a sense of opposing elements, of which a fierce collision is imminent." Philip Wakem emerges from the woods and admits to Maggie that he has followed her there, wanting to see her again. Maggie is frank—she is happy to see him and thanks him for the kindness shown to her and her brother in their youth and explains how she is sad that they cannot restart their friendship. Philip protests, asking Maggie to meet him in the woods now and then. He first suggests that it is their duty to repair the enmity between their families, that their meeting would affect no one, and finally that meetings with her would provide the only happiness of his days. Maggie cannot agree to meet him as it would thwart her purpose of putting other people's happiness in front of her own and her desire to give up her discontent with her narrow life. Philip rejects this as damaging asceticism and speaks of the need to hunger after "certain things we feel to be beautiful and good," like qrt. Maggie finally agrees not to make her decision today but to come again to the Red Deeps and tell him her decision then. Philip is happy but still slightly sad at his perception that she has never considered the possibility that they will become lovers.
Maggie returns home with a conflict within her. Philip returns home feeling that Maggie is the only woman in the world with enough love to love him in his deformity. He vows to be Maggie's "guardian angel," and to "do anything, bear anything for her sake."
Tom has been getting on in the world slowly but has become a credit to his uncles, especially his uncle Deane who acquired the warehouse position for him. Tom is frustrated by the slow accumulation of money and, about a year ago, took an opportunity to venture some capital with Bob Jakin. First, Tom needed capital to venture, and Mr. Tulliver proved too uneasy about losing money. Instead, Tom decided to visit his uncle Glegg with Bob to ask for Glegg to advance him some money to venture.
Bob and Tom meet Mr. Glegg in his garden. Glegg is wary of Bob, dressed in his packman gear, at first, but is won over by Bob's innocent talkativeness. Bob explains the plan to buy goods cheaply at Laceham and sell them for a profit. Mrs. Glegg calls the men in from the garden but is dismissive of Bob the packman. Bob senses that Mrs. Glegg would be a good target to whom he can sell his goods and begins buttering her up, speaking of her high-class status and of his knowledge of the Dodsons. Bob plays coy with the contents of his pack, insisting that they're beneath her tastes and prices.
The men explain the moneymaking scheme to Mrs. Glegg, who is first skeptical, then hurt—feeling as if she's been left out of a profitable plan. Bob returns to the subject of his goods and, after much more coyness, shows Mrs. Glegg his goods. Mrs. Glegg, entranced with stories of lesser women getting good deals, buys some muslin and net. Bob also gets Mrs. Glegg to lend twenty pounds of her own money toward the venture.
That gathering of the initial capital was a year ago, and by the time Philip and Maggie meet in the Red Deeps, Tom has a hundred and fifty pounds return, unbeknownst to his father.
Maggie continues to struggle with the question of whether to continue meeting Philip. She decides to tell him she can't, because it would have to be secret, though she feels that the friendship between herself and Philip is blameless and naturally good. Maggie meets Philip in the Red Deeps and tells him they cannot meet again, and Philip acquiesces but insists they spend a half-hour together before they part.
Maggie poses for Philip to continue a picture of her. They continue to have the argument in which Maggie sticks by her pious self-effacement, and Philip insists that she is unnaturally stupefying herself, instead of reaching for a full life. Maggie hears some truth in what he says but also senses that he is not completely correct. Philip argues against her self-denial in part because he knows it to be unnatural but also selfishly, because he knows it will cause her not to see him. Maggie asks Philip to sing her a song, which he does, but the indulgence of the music causes Maggie to insist that she leave. Philip offers a loop-hole to Maggie: he will continue to walk in Red Deeps and if they meet by chance, there will be no secrecy involved. Maggie's eyes consent and they leave it at that.
In Book Fifth, Maggie's internal struggle between self-effacing tranquility and the desire for a full, sensual life reaches a crisis point as a result of the figure of Philip. Philip's deformity is intrinsic to his role in encouraging Maggie against self-deprivation—Philip has suffered too much self-denial and lack of love in his life to romanticize that position, and his intellectual curiosity is equal to Maggie's, so he knows what she is denying herself. Throughout the personal and philosophical arguments between Philip and Maggie, the narrative encourages us to understand that, from a big picture viewpoint, Philip's understanding of Maggie's actions as self-denying is correct. Thus when Maggie continues to meet Philip in the woods, we see through the rest of Book Fifth that the effect on her is positive and affects others positively, such as Tom, who has "been better pleased with Maggie since she had been less odd and ascetic; he was even getting rather proud of her." Yet, the narrative also encourages us to be suspicious of the immediate motives behind Philip and Maggie's continued meetings. Both Philip and Maggie are portrayed as fallible. Maggie's natural need for admiration and love is egotistically gratified by Philip's presence, as when Philip prepares for a portrait of her in Chapter III, and Maggie's face "looked down like that of a divinity well pleased to be worshiped." Philip is portrayed as fallible through his own self-pity, which is illustrated in moments such as his commentary on his singing voice in Chapter III: "But my voice is only middling—like everything else in me." This self-pity (along with a genuine suffering at the lack of love he has experienced) leads Philip to be somewhat selfish in his motives for convincing Maggie to see him.
The second plot line of Book Fifth involves Tom's attempts to gain money more quickly by risking money in a venture with Bob Jakin. These two plot-lines, Maggie's secret meetings with Philip's and Tom's attempts to get the Tullivers out of debt more quickly, are alluded to in the title of Book Fifth, "Wheat and Tares." The phrase comes from the Bible (Matthew 13: 24–30), specifically a parable about a man who plants wheat in his fields only to have his enemy come during the night and plant tares, or weeds. The man sees the damage but wishes to wait until both the wheat and tares have come to harvest so that he can separate them out cleanly and save his wheat. In this metaphor, Tom is sowing the fruitful wheat that will get his family out of debt, while Maggie sows only weeds by going against her father's wishes. Yet, the parable also alludes to the sense that the narrative must continue further—to see Maggie's and Tom's respective actions played out—before judgements and classifications can be made.
The scene between Bob Jakin and Mrs. Glegg provides some needed comic relief in this serious and weighty Book Fifth. Bob continues to be a character that upends Tom's strict code of "fairness." Tom displays his generosity toward Tom, but continues to haggle, cheat, and misrepresent, though only to characters who seem to have it coming to them, such as Mrs. Glegg with her disproportional miserliness.