In theory, everything went perfectly.
He already knew that she adored Mawile - that much was evident from how much she doted over the newest addition to her team - and, once he’d tracked down the Mawilite, it was fairly easy to set it into a ring. When he stopped by Petalburg in search of Norman’s approval, the gym leader had taken one look at his nervous face and said “Well, it’s about time.” After finding him searching through Sootopolis for a proper site, Wallace had winked and informed him of an upcoming meteor shower right over the Cave of Origin, and there wasn’t supposed to be a cloud in the sky.
Everything was planned out. He would pick May up from her apartment complex in Mossdeep, and they would ride to Sootopolis on Latias’ back. They had the best seats in the house at the best diner in Hoenn, and the view of the sunset would be superb. Afterwards, he would suggest they go on a walk and just so happen to notice meteors streaking across the night sky. They would stop to watch and he would say something flattering and then he’d get out on one knee and produce the ring from his pocket and -
Well, you get the idea.
And, at first, everything went according to plan. When May answered the door, her hair was braided and she was wearing a simple red-and-black dress with a flared skirt. It was the most formal thing he’d ever seen her wear, yet it suited her perfectly. Needless to say, he didn’t exactly have to force any compliments.
That was when things started to mess up.
Clouds brewed on the fly there, and it was raining by the time they arrived. When they hurried inside, holding their bags over their heads, they were informed that their reservation had been canceled since it had been a seat on the roof. He was dismayed, but May just laughed and said she’d be fine with fast food. Unfortunately, though, that wasn’t the end to his bad luck. Although the rain cleared, the clouds did not, and, instead of waltzing through the starlight and watching the meteors fall, they found themselves shuffling around in near pitch-black darkness.
It was practically inevitable that he should trip over his own two feet and bowl straight into her.
And, naturally, May being May, she caught him like he weighed nothing, wrapping her arms around him with a casual “Whoa, whoa, whoa!” Gritting his teeth, he looked up at her and found that her braid was tumbling over her shoulders, the faint light from the far-off town illuminating one side of her face. “Are you okay?” she fretted.
And, without any control over himself, Brendan reached into his pocket, tore out the ring, and stuttered, “M-marry me?”
(A few months later, as she walked down the isle, beaming at him with enough enthusiasm to make even Norman smile, all he could think was ‘Arceus, I’m lucky.’)