For months, the couple's mutual friends Brooke and Jacob Schmitt had been trying to set Claire and Sawyer up. Claire was not interested; Sawyer was, but had been told Claire wasn't. Fast forward to what was supposed to be a girls night between Claire and Brooke, but plans changed last minute when Sawyer cancelled on Jacob (Sawyer refutes this and says he never had plans in the first place.) Jacob ends up tagging along for girls night (also our DD) and as the girls talk for hours -- Claire felt bad for Jacob, the third wheel. So, she said Jacob could invite a friend if he wanted. Brooke took the chance to immediately call Sawyer and invite him out. At the chance of finally getting to meet Claire, he cancelled his plans again to trek through the Country Club Plaza on one of the coldest nights of the year. Sawyer immediately grabbed Claire's attention, but the two would only share a few exchanges before going their separate ways. A few days later, frustrated that Sawyer hadn't reached out yet to ask her on a date and hearing that he wanted to pay her back for a drink he thought she paid for, Claire messaged Sawyer on Instagram to say, "Hey! Just want to confirm I did not pay for your drink Saturday... so great meeting you!" Sawyer then responded with ,"Well that's a shame. Would've meant I'd owe you a drink sometime." You know the saying that you can lead a horse to water but you can't make it drink? Turns out, you can buy it a drink instead.