Link's first hint that a woman might have romantic feelings for him came from the most unexpected of sources: Illia, his childhood friend and fellow caretaker of his mare Epona.
It also came to his attention rather suddenly and at the worst possible time. As the farmhand prepared to recover Epona from a previously irate Illia so he might make Rusl's delivery for him, the mayor's daughter, pale skin reflecting off of the springwater in the rising sun, paused in handing him the reigns, holding her delicate, thinner fingers over his rougher digits.
"But, Link...Can you at least promise me this? Just come home safely..."
Link's mouth went dry as he beheld the pink in Illia's bright cheeks and felt her fragile hands attempting to caress his palms in a decidedly un-friendly manner. Her overt statement of concern rose above the worry of a friend and stepped into the demand of a lover, with her obvious expectation that he would answer in the affirmative.
He tried to smile disarmingly, but could only manage a lame sort of grin as he realized the thought process behind her words. He would be away from Ordon, and consequently his friend, for the first time in many years. Illia, by the slightly demanding tone of her words and her clumsy attempts to hold his hand and make eye contact when he was in a desperate rush meant that she obviously expected some kind of declaration of mutual love before he departed.
As difficult as it might be for Illia to eventually admit, Link simply didn't see her in a sexual or romantic light. Certainly, he loved her, but did so in the same manner he loved Epona or Colin: as one of his best friends. Nothing more, nothing less. Her attempt to strike a pose alongside Epona, against the spring, were admirable if not forced and did little to attract him to the idea of confessing nonexistent attraction for a mutual friend in front of a mutual friend.
Unfortunately, no such statement was forthcoming as Link continued to smile idiotically, making the situation unbearably more difficult than it needed to be. Colin looked on, head tilted to the side in curiosity as his eyebrows furrowed in confusion at Illia's unexpected antics.
The conversation might have remained frozen in that awkward period of time if not for a totally unexpected intrusion by a Bulbin raiding party...
No further thoughts on the topic of women entered Link's head for a great while yet-not even after he encountered Princess Zelda for the first time. Taking on the shape and mentality of a wolf, however intelligent, dampened his ability to view Hylian women in a sexual light. Even when he watched the spirit of Illia, much later in in the Twilight-shrouded Lanayru province, tend to the Zora prince, he was unable to feel any stirring of lust that he knew he would've felt in small amounts as a human, even considering how he never could contemplate treating her as anything but a friend.
Once Link had freed the entirety of Hyrule from Twilight, however, and encountered her once again at the bar, he was both hurt by her memory loss-how her mind had thrown away nearly two decades of friendship-and relieved, in an incredibly guilt-inducing manner. If she didn't recall him, she couldn't go back to awkwardly coming onto him in an unwelcome manner...right?
Very wrong, apparently. Even without memory of their past together, she still exhibited most of the signs of obvious attraction, and while the barrier of their history had been removed, Link still felt...wrong reciprocating her advances with his knowledge of who she really was. So he quietly rejected her, ignoring the pained look that flashed across features before her concern returned to Prince Ralis's health.
Even Telma assumed that he knew her in a romantic light when she beheld him, what with her demanding that he 'Lend her his strength', which implied the existence of an assumed relationship. As much as it might hurt Illia to hear it when it would eventually come to a head after her memory's restoration, the two of them had no chemistry, whether romantic or not: a platonic friendship with plenty of secret sharing was all that Link possessed with Illia...or managed to possess at once point.
Fortunately, Link's other encounters with admittedly attractive members of the fairer sex went significantly better: soon after he'd dressed himself in Zora armor, Link stumbled across "Iza and Hena's Playground for Grown-Ups" and the namesake owners.
He had to admit, the older of the two, Iza, while frightening (and apparently cheap and rather overbearing, according to the Zora part-timer), had a wild, commanding beauty with her frizzy balled hair, two-piece clothing, and window of heart-shaped cleavage that seemed to want to burst out of her shirt...
Iza's rough and ready manner dissolved in the face of true danger, however, and she became similarly red-faced and tongue-tied upon getting a good look at him. Fortunately, her superbly eloquent statement that he was "Uh...Wow...You...Wow, what a champ you are!" was significantly less awkward and not entirely unwelcome given the beating he'd taken in the interest of protecting her from some Shadow Beasts.
Her invitation into her home and shop so soon after she became so obviously smitten could have easily ended in sex if he hadn't ripped his arm open and she wasn't obviously looking for a way to exploit him. After having patched up his wounds and spending a decent amount of time obviously ogling his biceps, by how she bit her lip and rubbed her hands over the lean muscle as she wrapped a bandage around the cut in his arm, Iza was reunited with some of the gruffness that he sensed lay within her. She nearly demanded Link's assistance with unblocking the river, though she did throw in some statements about 'needing a guy around', the implications of which (combined with her cleavage and breasts straining to escape her shirt) brought a blush to his cheeks and a tightness to his pants. Compared especially to Illia, Iza's infatuation was mutual in the slightest, most welcome way.
Her sister, Hena, on the other hand, was more like Illia. Illia was conventionally beautiful in an immature way, pale, soft, and delicate, and Hena was...well, cute.
It didn't exactly hurt that her flirting didn't feel forced or awkward, likely due to a lack of history. In fact, when he found himself reeling in a rare heart gem when she had offered to help him fish, her next words felt genuine and blush-inducing.
"Oh, whose heart did you catch?"
Much too soon afterwards, when the younger Hena had challenged him to choose between her overbearing roughly beautiful sister and Hena's own immature looks, Link had awkwardly and automatically responded in favor of Hena, much to her delight. He would've felt guilty for being a little dishonest if Hena hadn't been so happy. He honestly found neither of them terribly appealing, though they were decently attractive.
The next woman to make her feelings known to him was, oddly enough, Midna herself. After relaying the history of her people in a manner that approached a confession, Midna floated over the night-cooled sands of the Gerudo desert. Link was too busy absorbing the painful details of her story to notice her place a tiny hand on his cheek, her fingers vibrating slightly with the power keeping her afloat, until she had already done so.
Eyes widening, he looked forward, straight into her red pupils, and was shocked by the dull, depressed gleam of her eyes and her begging tone.
"You'll come with me, won't you?"
Link's throat stuck at the complete resignation in her voice, and he caught the underlying meaning behind her words: a request not only for him to help her find the Mirror of Twilight, but a personal plea for his companionship.
The Hero couldn't help but smile. Now this was something reasonable. Not only was her presence welcome, considering how she had evolved from outright maliciousness to respect, and then understanding, but he would do what he must to help her and keep her close.
It might've not been romantic at the time, but it was the most genuine bond he'd felt since the instant connection with Zelda and his early days of friendship with Illia, before the latter had mucked it up.
"She's a beautiful young lady named Ashei. If you have a chance to meet her, you should definitely take the time to talk to her, OK, honey?"
Link couldn't help but sense that Telma had made a point of stating the first half of that sentence when it could have gone unsaid. It was just a feeling, but a strong one.
Probably aided by her knowing, 'I'm-doing-you-a-favor' wink. And her history for attempting to pair him off, or at least tease him for his handsomeness.
Of course, she'd certainly made a factual statement: Ashei was conventionally gorgeous, if very rough-mannered, and Link shuffled awkwardly as he beheld her blush, though she would likely have blamed it on the cold of Snowpeak mountain if he had pressed the subject.
He was wondering when he'd get an interaction with an attractive woman where she didn't display her interest so overtly. It obstructed other objects of interest, such as advancing further in his quest and keeping him from becoming distracted.
Fortunately, he knew that she was attracted to Shad, the well-educated scholar whom he had met at Telma's bar. His wolf senses had, during his desperate search for Princess Zelda, picked up the musk of a woman aroused, and she certainly didn't find Auru, the old warrior who was the only other person besides Shad nearby, sexually attractive.
Unfortunately, Midna had caught onto how women tended to react around him and was ceaselessly teasing him for it when they found a spare moment.
"Link, it's getting kind of awkward living in your shadow yet being able to know how your dreams of Zelda are making you react. Can you at least try and suppress your stiffness until the times I'm not right under you?"
The fact that it was well-intended teasing didn't exactly comfort Link, though he managed a rare smile when she found a particularly clever thing to say about either his masculine reactions or how girls might be picturing him without his shirt. Key word being 'rare'.
As heartless as it might sound, Link couldn't help but feel a little under pressure as Illia gazed at him knowingly, expecting the same confession now as she did before her amnesia, before this entire ordeal. Even with her gift of a horse whistle and the pointed vacancy of Gor Coron and Renado, Link had gone through too much, evolved to such an extent since her last awkward proposal for him to consider it again. Not with the knowledge that he could never reciprocate her romantic love.
Still, he couldn't break her heart, and genuinely hoped that she would remain safe. And so, Link smiled back at Illia, the gesture radiating love of a different kind than Illia hoped to see.
Link was, frankly, having a little trouble keeping focused on what the Great Fairy was saying. It may or may not have anything to do with the fact that the surprisingly flirtatious immortal seemed to be entirely nude, and that her hair seemed to be doing a poor job of disguising her nipples from his gaze.
...Not that he was looking at her chest, of course.
Her eyes glinted mischievously, and Link gulped, his pupils flicking back up to her own eyes as the Great Fairy took a step forward, her hand meeting his cheek. Instantly, his mental confusion dissipated, the agony of dozens of chambers full of foes forgotten as her soothing touch soaked through her fingers into his skin. His distinct blue eyes became hidden by his heavy eyelids, and the Hero of Twilight let out a monumental sigh of exhaustion and relief.
"If ever you need my assistance again, visit any spring..."
His eyelids flew open as he started at the sound of her voice, having temporarily blotted her words out of his head. The distinct smile, blush, and undertone Link was getting to know well were very visible on the Great Fairy's features. He was mildly startled that an immortal was displaying such obvious attraction for a mere Hylian, even one as skilled and important as himself, but he supposed her judgement was superior to his own.
...And as he found himself falling unconscious, knowing that he was being transported out of this challenging gauntlet, Link swore the Great Fairy's hair had swayed just enough to the side that he could behold her chest in all its glory.
Link hadn't had the chance to meet Zelda in his humanoid form before now, and even if it was under quite possibly the worst circumstances possible, while they were still in combat with a fellow Triforce bearer, seeing her sky-blue eyes and her beautiful body brim with life of her own, not the perversion Ganondorf forced on her, was refreshing the void of attraction he'd felt since leaving the Great Fairy.
Of course, the gravity of the situation tempered his reaction, even as Zelda turned away from Midna to behold him, the now-familiar rose on her cheeks and quickening of her breath alluded to her attraction. Still, the bearer of the Triforce of Wisdom knew that this was not the time, and before she could so much as address him, Ganondorf had recovered...and Link, to his unmitigated horror, found himself dissolving into black, formless shapes, a sign that he was teleporting away, against his will, as Midna invoked the Fused Shadows to battle the champion of Din.
The crushing hurt he felt in his heart could only be matched by that which the Princess felt for her similarly titled friend, but they had no time to grieve. Ganondorf was upon them, but found the Blade of the Sages piercing empty air instead of the flesh of a Hero.
Zelda's head remained bowed as she deferred to Link, begging him for a granting of power he wasn't sure he had. Looking over her bent form, Link couldn't help but feel as if she was asking more for comfort and contact after the death of their friend and in preparation for Ganondorf's final stand than any kind of actual gift.
Without thinking, Link held out a blood-caked, worn, gloved hand for Zelda to take, his lips slightly upturned as her similarly blue eyes greeted his, a sad smile ghosting across her face as her immaculately clean white gloves sullied themselves in the act of joining hands. Their fingers interlocked as light overtook them, and Link would've felt as utterly at peace as he had with the Great Fairy if not for the situation.
That shape on the hill...it couldn't be...
Link's mind raced as the Light Spirits faded. They had that kind of power? The kind usually reserved for Gan-
The Hero of Twilight noticed his legs carrying him up the incline of their own accord, and he threw speculation to the winds as he gave what little strength he had to his strides, the choking grip of hope welling up in his chest, smothering his breath yet bringing relief in its wake.
He could see the shape in front of him, and confusion blanketed him for the briefest of moments as it stood up...taller than the Midna he had known, taller than himself, taller than Zelda, nearly as tall as Ganondorf...and turned to face him.
The instant he beheld blue skin and red eyes, the latter glinting in happiness and anticipation, he knew that his suspicions had been proven correct. He blinked, started and gasped at the epiphany.
The gorgeous woman standing before him was Midna, the sarcastic, slightly adorable imp he had known for many months. The similarities were too close for her to be anything else.
...Seeing her now, he had difficulty remembering what she used to look like, without her long, very visibly delicious legs, stunning, well-sculpted features, and a bust that seemed naked to his eyes.
"What? Say something!"
Her voice, too, seemed to have shifted: now she sounded like the best possible cross between Zelda's calm, regal tones and her old foreign mischievousness. He continued to remain silent, out of shock and appreciation for the moment and Midna herself.
"Am I so beautiful that you've no words left?"
The supple ripple of visible laughter shuddering through her body and the sensual teasing in her eyes would've gone straight to his manhood if he wasn't bleeding out. Seconds before he fell forward, happily unconscious, into her arms, the Hero of Twilight allowed himself a smile, the first of many that would cross his features after his travels had come to an end.
Link had been robbed of speech, and Midna truly was beautiful.
The Mirror of Twilight wasn't the only thing that shattered when Midna left.
His lower lip trembled, throat catching as he willed the tears that thoughtlessly sprung to his eyes to vanish. But in the end, Link was powerless to hold back a monumental sob, the outburst of all the pent-up sorrow, trials, and love his journey had bestowed upon him. Nor could he ignore the equally devastated silence of Princess Zelda, even if he had wanted to.
Link reflected on his Twilight Princess, and pain that no doctor could formulate a medicine to treat burned his heart.
His memories of Midna would torture Link for the rest of his days, forever marring the rest of his life. No matter how many times Link found himself on the brink of despair, Zelda mended his heart each time Midna's memory shattered it to pieces. But it would never be enough to make him, or Zelda, forget Midna, never dishonoring her memory by erasing it from their minds.