Regulus had never been one to back down from things.
Whether it was a challenge, a project he merely did not want to do, or just something as simple as a game of chess that he almost rolled his eyes at, he never backed down from anything. He supposed it was in his blood, since The Noble House of Black always seemed to be too prideful in what they did and what they favored, but, even then, that just fueled his pride even further. To think he was doing something that his mother might be proud of later.
Yeah, that seemed to float his boat quite a lot.
The one thing he prided himself on never backing down from was bets. Regulus’ intuition was scarily accurate. Not that he would brag about it, but, he knew loads of things before they tended to happen. Or he just bribed some poor fellow to tell him everything he needed, but, hey, either way works like a charm, does it not? So when Barty came up with a bet to see who could woo a girl with their natural talent within 2 months and bring back proof of it between him, Regulus, and Evan, oh, Regulus knew he had to win.
He almost didn’t realize that included Barty choosing who they had to woo, and of course, Barty chose you for Regulus. He didn’t mind. You seemed like an easy target. Plus, he had two months to get you webbed around his long finger, and he knew it was possible. He just had to ignore the dreadful feeling that constantly lurked around in his gut.