The first time Aelwynn met Sylvanas' gaze was as a young, frightened child. The Ranger General of Silvermoon had saved her when her family was killed and raised by the Scourge. She found comfort in the woman who saved her very young life, a woman who had come and gone.
The second time Aelwynn met Sylvanas' gaze was in the throne room of the Undercity, a young hunter bringing a family heirloom to the Banshee Queen that she had found in the former Ranger General's old home.
The third time Aelwynn met Sylvanas' gaze was after Hellscream was put in as the Warchief. She came offering her services as a spy, wanting to make sure that the Dark Lady knew she had supporters. That may has well have been the first time their eyes met.
By the fourth time, Aelwynn had fallen for the Dark Lady. They corresponded through letters while the young Hunter was stationed all over Azeroth. When she was called to Outland, she could sense Sylvanas' concern. Her older sister had disappeared through that portal and was never heard from again. She may not have been in love with the blood elf, but the thought of losing her the same way she had lost Alleria scared her.
The fifth notable time they locked gazes was in Northrend. Aelwynn and her fellow raiders had killed Arthas. She had sensed the fury and hopelessness in the Banshee Queen, knowing that the sense of confusion was eclipsed by the relief in knowing that the monster that haunted their dreams was dead.
The sixth time had been electrifying to say the least. Deathwing was terrorizing Azeroth, and Aelwynn had just returned from working with the Aspect of Time, Nozdormu. The End Time had been heart wrenching. Seeing Sylvanas a broken shade of the woman standing before her, nothing but the rage, pain and hatred that lived on after her soul was completely broken. The others were disturbing to her, seeing Jaina, Tyrande Whisperwind and Baine Bloodhoof tormented in the same ways was horrible, but seeing the beautiful undead High Elf in that constant state of torment hurt. Killing her was even more awful. She had come to Sylvanas, worrying the Banshee Queen with the lack of reaction to anything happening around her. The Dark Lady had touched her, cupped her cheek with a bare hand, and she had broken. They had lain together before, but none of it compared to that moment.
The seventh time had been right after Sylvanas had returned to the Undercity, the plan to rid the world of the disgusting beast known as Garrosh Hellscream failing when Sylvanas' sister Vereesa turned her back on Sylvanas. The worry that Sylvanas had experienced when Aelwynn came back from the End Time was mirrored in the Blood Elf's gaze as she saw her lover covered in the blood of the wild animals around Tirisfal. That had been the last time their eyes met.
Now was the eighth time. Aelwynn met the gaze of her Warchief, the haunting red eyes set in the beautiful face she missed. Her heart had broken when Sylvanas had shouted at her, telling her to leave and never return. She hadn't understood why their lives were spiraling so out of control until this moment. They were never destined to be together. Life and death were always opposites, Sylvanas had once said that though opposites attract there was little hope for such a futile union.
In the future, Aelwynn's gaze will meet Sylvanas' one last time. Followed by one last breath, and a Banshee wail will ring through the air.