Hey guys, here’s a fun one I’m stuck on. It wouldn’t be an understatement to say that bratty girls are my weak point. She came into this interaction already with quite a bit of attitude. I went with a playful misinterpretation of her hope in my abilities by saying she already has her hopes up about me. She took the literal interpretation and shut it down. My roommate came up with the last line which I thought was funny af so I sent it for the self amusement but it doesn’t leave much room to keep the interaction going in a positive way.

Couple of questions:

Would my messages have come off as more obvious jokes if I added a smirking emoji?

Should I have said something differently?

Is there a way to keep this going while also making her ego take a step down so this can actually go somewhere? Maybe with “am I wrong?” Or something of the sort?