Zak: This situation is definitely ripe for awkwardness. I would think that your stepmom would want to avoid creating any kind of situation like this simply because it will likely take a lot of the attention away from her wedding if people are finding out that you are trans* right then (and likely gossiping about it, trying to figure things out, and potentially even causing a scene). If you’ve already tried to reason with her about this without any luck, the next thing you should do is to go to your dad. Depending on your relationship with your father, he might be a good go-between to help you settle things with your stepmom. He might very well want to stay out of it, but it’s his kid and his wedding too. If neither of them are willing to work with you and you really feel like you can’t deal with her family, you might want to consider telling them that you’ll be unable to attend under these circumstances. That has the potential to cause a huge rift in your family, so be careful if you do decide to go that route. However, what your stepmom is asking you to do is to go into a situation in which you are trapped outing and explaining yourself to completely unprepared and likely unaccepting people (and you’re right, with warning they are more likely to avoid you if they have a problem with it than say anything to your face or cause a scene). This is extremely unfair to you and, as you mention, definitely awkward and also degrading.