I squirmed in my chair at a hip coffee shop on the Upper East Side. As chat we over barely consumed lattes it becomes evident that we have absolutely nothing in common. Not only that, he was interrogating me on my untraditional career choice. With each question, I felt smaller and smaller like he was sizing up my IQ based only upon the premise of my choice to pursue acting professional and my fuschia heels. Suddenly not only did I feel awkward but I felt angry. Forget this guy! I didn't owe him anything and I certainly didn't need to be looked down upon for something he didn't even entirely understand. "I've gotta go," I blurted. He seemed surprised. Maybe he thought it was going well? I don't know. I clumsily stumbled out of my seat and repeated myself. "I've gotta go. Bye." I don't really remember what happened after that because I made a beeline for the door and the five train. I wondered how this could be such a poor match after pouring over his Bumble and Facebook profiles, and having a number of good conversations with him over text. Alas, there I was on 68th and Lexington thinking "I need to get smarter about this." As I became seasoned in online dating, I developed some tactics to making these awkward first dates go as smoothly as they can.