Roughly three weeks ago she goes in and he seems really sad and bummed out. Apparently, he just broke up with his girlfriend. Vanessa jokingly says, "I will fuck the sad out of you." It was that day he started texting her back.
He told Vanessa how he has been wanting to take her up on her offer (fucking the sad out of him), but he was worried about me finding out. She explained to him that it's ok if she fucks and from that point they seemed to be on the same page.
He asked her a picture which Vanessa happily sent.