5. Kylie Jenner & Tyga

When you are dating a Kardashian, you better be prepared to be extravagant! Thankfully, Tyga knew this to be the case when he dropped a massive $50,000 on a luxury designer watch for his boo, Kylie Jenner. That same Valentine’s, the couple also spent the day flying around New York City in their own private helicopter. Not bad, huh!?