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.

Analysis

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.