3 attempts.
First, mischievous, tease, optimist
Second, adventurous, witty, confident
Third, clumsy, flirty, innocent
All three did things from outright mean "or are you being boring as usual?" In the second line of dialogue. To just antagonistic "finally admitting you're a nerd" when I said I played a video game earlier.
The LLM seems to be built on a VERY antagonistic conversational model.