The high level of ambiguity in the third quatrain is thought to be deliberate and intended to derail a simple reading of a conventional sonnet with questions of who is being referred to. Beguiles is used here to mean tricks or deceives. The poet, motivated to stop the torture and conjure the image of the young man, beguiles (guil’st) the evening. In a similar way, the poet flatters the dark (swart) complexioned night. The third quatrain begins (line 9) with the poet telling the young man that he (the poet) flatters the day by telling him he is bright, and that he graces the young man even when the clouds hide the sun. The Day and the Night are disturbed that the young man, or at least his image, will not appear to the poet, so they attempt to torture it out of him. If toil is interpreted as the work of a poet, then the torture is a metaphor for the poet's anguish that his efforts to find poetic expressions and metaphors to describe the young man are not getting closer to the young man, but are moving away. Day tortures the poet with toil, Night tortures him by causing him to lament how far off the poet is from the young man.
In the second quatrain, Day and Night are personified as a pair of tyrants who were enemies to each other, but who have now shaken hands to join forces to torture the poet. So, the word toil appears to be referring to the poet's work: the search for words and metaphors to describe his fair young friend. The toil is the toil of travel, and the description of travel in the previous sonnet (Sonnet 27) is the journey that takes place in a poet's imagination. The concern is that at night he is prevented from resting, and by day he is oppressed by toil. Sonnet 28's first quatrain begins questioning how the poet can return to the young man in a happy plight.
All four describe the nightly disquiet that keeps him awake, and the imaginative journey that occurs in the mind of a poet. Themes in Sonnet 28 begin in Sonnet 27, and continue into sonnets 43 and 61: All four sonnets find the poet alone in bed at night in the dark trying unsuccessfully to conjure with his mind's eye the image of the young man.
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