Gallery
Sasha and Jackson met in law school, when Sasha was invited to a party at Jackson's house and she immediately noticed that his wine collection rivaled her own. That night, Jackson lit up the dance floor and Sasha immediately knew they would be friends. It wasn't long before Jackson asked her to check out a wine bar with him, apparently intending it to be a date. But he was vague about his intentions and Sasha doesn't like vague so she invited their other friends to join. Jackson dodged the friend zone expertly, going with the flow for the evening but being very clear that he knew what was up. The two have been challenging each other ever since.