Jumping on the headcanon bandwagon that Wind Rider is Lightning Dust and Wind Sprint father, tho i don't believe that Clear Sky is the mother of Lightning, so here is my interpretation!.
1) "Make sure to capture my good side when i cross the finish line" "You know i always do, pretty boy"
Here we a have a much younger Wind Rider along with Lightning's bio mom, Dazzleflash, a photographer. They met when the Wonderbolts had a photoshoot, and flirted the whole session. They weren't an official couple, more like (best)friends with benefits, since the two of them had other flings. Wind's career was at its greatest when Dazzle disappeared for a while, Wind was worried but couldn't find her. It was many months later that he was visited by Ray Stinger, Dazzle's brother, who carried a little filly in his arms. He told him that Dazzle died during childbirth, that the filly was his and that he couldn't take care of it, since Ray already had a pretty big family.
2) "Ladies and Gentlecolts, i present to you my biggest fan, my little Lightning Dust!"
After he grabbed little Lightning in his arms, Wind panicked, not only was his best friend gone, but he also had a daughter now, and the Mustang Marathon was nearby. He didn't wanted to expose Lightning so soon, but foals are always good publicity. So as he won, he introduced the whole Couldsdale press to his daughter. From that moment, his fame skyrocketed and he seemed like a great father in camera, but in reality little Lightning was raised by nannies and didn't saw her father so often, only in her training sessions to become "the greatest Wonderbolt after his father"
Wind was a party animal, and he often made parties in his penthouse. In one of those parties he met his (ex) wife, Clear Sky.
3) "C'mon sis, he LITERALLY was looking at you" "Nah Lils, you are way prettier than me"
The twins Lily Lace and Clear Sky are the daughters of a canterlot socialite and a cloudsdale philanthropist who gave LOTS of money to the Wonderbolt's Academy, because of that, they were often invited to parties and events. As we know Lily is a designer, and Clear was her model.
"Um, excuse me miss" "Uh? Oh hi little one, what's wrong?" "I-i can't find my daddy, could you please help me find him?" "Sure darling, wait for me Lils"
They found Wind Rider half-drunk with his peers, and Clear Sky was about to go on him that he shouldn't leave a dilly so young in these kind of parties…but there was something charming in him, how he tried to calm Lightning, and he was also handsome too. Wind also realized how pretty the unicorn was, and after putting Lightning to bed, the two of them spent the whole night together.
Not long after they where the hottest couple in Cloudsdale, and married very soon. But old habits die hard, and Wind was still seeking mares under Clear's nose. They had many problems in their relationship, and Clear only stayed for little Lightning, she had grew very attached to her, and Lightning felt the same with her step-mom. After many years of couple therapy, they decided to give a try at having a baby, maybe that would strengthen their marriage…it didn't. The months that Clear was pregnant Wind cheated on her.
They stayed together some years after Wind Sprint's birth, but they didn't loved each other anymore, and Lightning was a grown mare, so Clear didn't felt so guilty when she divorced Wind Rider.