6. Alana De la Garza
When Trump met this beautiful Latina at a red carpet event, he reportedly asked her, ‘Are you Mexican or just look like you’re from Mexico, because I can’t tell under all that awful makeup.’ Maybe not the best way to woo a pretty lady, but his brashness worked and Trump and De la Garza soon flew down to Puerto Vallarta to enjoy some time alone. But after De la Garza accused him of being racist against Mexicans, Trump proved his loyalty and bought her an island. It wasn’t enough to keep her interest, however, and De la Garza broke things off. She kept the island, though and named it ‘Isla De la Chump Trump,’ which has become the number one tourist destination for Mexicans.