Complex sentence: After stealing his lacrosse coach's Viagra, he relied on Blair and her alumnus father's connections to get accepted to Yale, although he eventually left to sail around the world with his father's Navy mentor because he is unable to choose between Blair and Serena.
Split into simpler sentences: After stealing his lacrosse coach's Viagra, he relied on Blair and her alumnus father's connections to get accepted into Yale. Nate eventually left to sail around the world with his father's Navy mentor because he is unable to choose between Blair and Serena.