Haha it's nuts the way some people on this forum interpret Tess's behavior. There was another guy who thought Tess's character sucked because she "wasn't too good with the boys" or something along those lines.
First of all, OP, you are missing a key piece of dialogue in the conversation you talk about. He clearly says, "I heard you've got some merchandise", referring to the fact that Tess is a well-known smuggler in the Boston QZ. This was made abundantly clear to me the very first time I played. The "pretty lady" remark is really nothing out of the ordinary - prob just a sleazy, underlaid dude, hitting on an attractive (in that post-apocalyptic way, you know ) woman. And because she *might* have had an intimate relationship with Malick at some point suggests she was a prostitute?
It's too bad that after creating such a masterpiece in terms of storyline and dialogue so much stuff seems to go right over people's heads: "What's up with that chick, a woman is telling me what to do? i have to follow a woman around??! Grrr!!! Wait, they are talking to her in a sleazy way, must mean she is a prostitute! I have to follow this stank prostitute around for the first hour what the **** Naughty Dog!" Not to mention it kinda sucks some people still think of women in this somewhat old-fashioned way, even though undoubtably they meant no harm and don't even realize what they imply.
People are crazy haha
I think you're just extremely horny, and are most likely just hitting puberty. They could mean a number of things, but I'm guessing it all meant that she, oh I dunno, brought ration cards to them? Brought supplies to them? Helped them through the QZ to find more supplies, helped them OUT of the QZ? lel