Shimshon's first date

The first woman in Shimshon's life was a Philistine woman from the town of Timnah, whom he sees when he happens to be in the town. He then asks his parents to set him up with this woman, and after expressing their surprise, they agree. He goes down to Timnah with his parents. He then appears to separate from his parents, as he is alone when he single-handedly defeats a lion that he comes across.

In 14:7, it says "Vayeired Vay'dabeir el ha-isha" - And he went down, and his spoke (el) the woman".

Rashi quotes Targum Yonasan ben Uziel, who translates "el" as "regarding", explaining that Shimshon spoke to the woman's relatives.

Radak gives two possibilities - either that he spoke to her relatives asking that they give her to him as a wife, or that he spoke to the woman herself, asking if she would marry him.

Metzudas David says that he spoke to her, to determine if she was intelligent, and found that she was.

Malbim says similar to the Metzudas David, that he spoke to her to determine her intelligence, her midos, and whether she liked him.

I recall hearing that the Rambam explicitly says that the woman converted, so perhaps one can read this into the conversation that he had with her (at least according to those opinions that said that he spoke to her in person).