What obstacles does Romeo face during the course of Shakespeare's Romeo and Juliet?  

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Romeo has a varying degree of success in overcoming the obstacles he faces in Shakespeare's Romeo and Juliet. The ultimate obstacle is to be with Juliet despite the bitter feud. Unless you believe the two are together in heaven, Romeo fails in clearing this hurdle.

The first obstacle is his unrequited love for Rosaline. He becomes depressed because Rosaline avoids his affections and decides to stay celibate. Romeo says, in Act I, Scene 1:

She’ll not be hit
With Cupid’s arrow. She hath Dian’s wit,
And, in strong proof of chastity well armed,
From love’s weak childish bow she lives uncharmed.
She will not stay the siege of loving terms,
Nor bide th’ encounter of assailing eyes,
Nor ope her lap to saint-seducing gold.
O, she is rich in beauty, only poor
That, when she dies, with beauty dies her store.
Romeo is much more successful in his love for Juliet. The girl is swept off her feet and they kiss within a few minutes of meeting each other. They part ways at the end of Capulet's party but...

(The entire section contains 685 words.)

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