How does Shakespeare makes the relationships between Man and Woman heart-wrenching and complex to you? ( A MIDSUMMER NIGHT'S DREAM)Take evidence from the entire text.
Though Shakespeare does make the relationships among his characters complicated in Midsummer Night's Dream, the play is a little too light-hearted to be accused of being "heart-wrenching." He looks at love and relationships through the characters, giving each couple a different set of complications that they must deal with and resolve.
First, you have the relationships of the two high-born couples Hermia & Lysander and Helena & Demetrius, which Shakespeare examines through the lens of comedy. The couples are practically interchangeable. Both women are willful, stubborn, and smart. Both men are proud, arrogant, and quick-tempered. They are all upper-class and used to getting what they want.
The complications arise through the intervention of the fairy kingdom and the plot device of the forest, where anything can happen, and does. If not for the machinations of Oberon, assisted by Puck, the outcome of the story might have been different, but one never knows. If Hermia and Lyasander had not become lost, they would have fled Athens and perhaps Demetrius would have come to his senses and shifted his attention back to Helena. She is really too comic a character for us to feel badly for her, and it seems that she would survive, no matter what. As it it, Shakespeare makes fun of romantic love with the two couples and the juice of a little flower.
In a sense, the only relationship that could be even peripherally "heart-wrenching" in the play is Bottom's with Titania, but Bottom is such an ass even before he is turned into one, that, again, it seems that his irrepressible ego would see him through any situation. Moreoever, he sees his affair with the fairy Queen as a dream in the light of day, not sure if it even really happened.
Titania and Oberon's relationship is one of powerful equals; their quarrels are petty, and there is never any indication that they would not ultimately reconcile. They clearly have put up with each other's affairs in the past, and probably will in the future.
The other romantic relationship, that of Theseus and Hippolyta, is also between individuals of equal status, but Hippolyta is a prisoner of war. That would be considered "heart-wrenching" if she did not seem to be so willing a captive. She and Theseus are in love, and he has, in his way, actually apologized to her, admitting that he wooed her with his sword, but now wants to marry her and change her status back to royal.
So, while each set of relationships has its complicating factors, by the end of the play everything is smoothed over and order is restored, even in the fairy kingdom.