Obviously that message was written for males only. When it mentions "If you're lucky, she might even invite you along", the "you" is the male recipient of the message who convinced the lady involved to enter the contest.
The entire thing is a poor implementation of what was probably an excellent idea in the beginning. As noted already in this thread, as it is currently worded it is just as likely to alienate women as it is to encourage them. You would think marketing folks would have learned by now to stay away from even intimating that a women needed a man to get her into riding, or to teach her anything about it. Oh well, it just reinforces my beliefs about the "rocket scientists" running the MoCo (into the ground).
Never met Karen Davidson or had any dealings with her, so I wouldn't know if traveling with her would be considered a desirable thing or not. Maybe the ladies would rather have a choice, Karen Davidson or George Clooney for instance?
Jerry