How does Feste’s song in act 2, scene 3 foreshadow events and act as matchmaking in scene 4?

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In act 2, scene 3, Sir Andrew and Sir Toby are drunkenly amusing themselves until Feste arrives and they ask him to play a love song for them. The song Feste sings foreshadows the happy romantic ending of the play, when Viola reveals herself and her love to Duke Orsino and Olivia weds Viola's twin, Sebastian.

O mistress mine, where are you roaming?
O stay and hear, your true love's coming,
That can sing both high and low.
Trip no further pretty sweeting;
Journeys end in lover's meeting,
Every wise man's son doth know.

What is love? 'Tis not hereafter;
Present mirth hath present laughter,
What's to come is still unsure.
In delay there lies no plenty,
Then come kiss me sweet and twenty.
Youth's a stuff will not endure.

Although the "journey" of the play indeed ends "in lover's meeting," I believe the second stanza of the song has more immediate connections to the thematic link between love, deception, and time in the play. Feste warns that love "tis not hereafter", meaning it will not be around forever, just as "youth's a stuff will not endure." Similarly, he counsels that delaying love provides no benefits and therefore may be foreshadowing how Viola, who has previously claimed that "time . . . must untangle this not I," must come forward as a woman and embrace her love of Orsino wholeheartedly before she can begin to reap its benefits. In this way, Feste's maxim that "present mirth hath present laughter" beseeches the characters to make merry in the present moment rather than squander precious time on useless intrigue.

It isn't made clear whether Feste's song in Scene IV is a form of conscious match-making, but it is certainly the counterpoint to his song in Scene III as it tells the tragic tale of a lover who hid his love and died of it. In this way, it does urge Orsino and Viola to express their love rather than live in the misery of hidden love. Deliberate or not, Feste's song also sparks a debate between Orsino and Viola about whether women can feel love as deeply as their male counterparts and this debate almost leads Viola to unwittingly reveal her true, feminine, identity.

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“O mistress mine, where are you roaming? / O, stay and hear; your true love's coming, 

 That can sing both high and low: / Trip no further, pretty sweeting; 

 Journeys end in lovers meeting, / Every wise man's son doth know.”

I think the lines that you are asking about are the above lines.  At this point in the play, all sorts of mix ups have happened.  They will continue to get more convoluted as the play continues.  A love triangle between Viola, Orsino, and Olivia is just the beginning of all of the mix-ups in the play.  Viola believes her brother to be dead, Malvolio is just a ball of negativity, etc.  Then Feste sings the above lyrics to Sir Toby and Sir Andrew.  It speaks of lovers finding each other, and a love journey coming to a happy ending—which is exactly what happens at the play's conclusion when Viola and her brother are reunited and the love triangle is resolved as the couples wed.

In scene 4, Feste's song is about unrequited love, which Orsino, Viola, and Olivia are all experiencing.  The song is about how that man dies of sorrow.  It's a form of matchmaking, because it's inadvertently encouraging the listeners to not worry about unrequited love.  Forget about it.  Go find someone else, or you will die sad and lonely.  It's very much in line with what Benvolio tells Romeo in Act 1 Scene 1 of Romeo and Juliet: forget Rosaline; there are plenty of other women. Feste's song is pushing his listeners to do likewise. 

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