we all know when gabby met xena she was a virgin in every sense of the word.Do you think that she ever crossed into the dark side with some of the things she did when she was with xena..?

I don't think she did but I think she felt like she had in Season 4 when she went thru that peace phase with the Eli storyline.

I think she found the darkness in her more or less. Season 4 was a huge turning point for her character like WXF said and Season 5 & 6 was more of a mature, wiser Gabby.

Season 3 Ep 17 "Forget Me Not"
Ooof.

Good question.

I think one time Gabrielle crossed into the darkside was when she betrayed Xena to Ming Tien.

That's what came to haunt her in Forget Me Not.

Another time was when she failed to kill baby Hope. This was probably a bigger journey into darkness because it lead to the evil adult Hope and later to the Destroyer.

In both those situations Gabrielle deceived Xena, the person she loved the most in the whole world. As a result she put Xena's life in jeapordy, and cost Xena her son.

You can't get much darker than that.