LMsA said:
"He's deliberately muddling the issue by playing semantics (dating, seeing, engaging with) but evidently they all mean the same thing."
It's when people use these words games that court interpreters have to "stop interpreting" and ask the judge to allow them to clarify with the person giving the testimony. Court cases can be won or lost depending on an accurate interpretation. Also, interpreters can be sued for misinterpretations.