I won’t rehash the list of lessons that you can or can’t draw from this experience – you already figured them out. I do agree that it makes sense to apologize to her for putting her in an uncomfortable spot. Of course you should do so in a way that does not tip her off to the fact that you KNOW that to be the case – she’ll wonder where/how you learned that, which could lead to even more awkwardness.

Sadly, we know that there is a not-huge-but-not-tiny-either portion of the population that is simply not ready to accept any forms of trans expression. I find it discouraging and upsetting when anyone would allow a prejudice to trump a real friendship (even the friendship between a server and a patron). We cannot change that fact. What we can do is continue to be friendly, outgoing, positive…and unapologetically trans. We do far more good than harm in enabling the community to learn who we are – even at the cost of occasionally painful episodes like this.

I do understand the distinction you are making between apologizing for who you are (which you won’t do) and apologizing for the way in which the situation unfolded. It is very hard sometimes to distinguish between acceptance and mere politeness, especially on the part of those we don’t know well. Which brings up an interesting issue in my mind…..

I think that the code of conduct for people in the service professions essentially requires them to feign acceptance of everyone and treat them with the appearance of respect, regardless of their personal feelings. I know that when I worked in retail years ago, I served every type of customer politely and graciously and never let on if I thought something was “off” about them. Only after they’d left would I turn to my co-workers and say “Phew! That guy’s B.O. nearly made me pass out” or whatever. Understanding this, I have to cringe a little when I hear CDs brag about how well they “passed” to store employees and how the sales help thought they were cute and so on. Yes, sometimes (a lot of times, maybe) this is the case, but you can’t always judge the true acceptance level of salesclerks, waiters, and other service staff by how well they treat you.

Don’t get me wrong, I am VERY glad that the rules of politeness exist and are observed by most people in public situations. I am just pointing out that it makes it very difficult for any of us to judge how we are really perceived.

So in closing I’ll just say again that I am very sorry this happened, but glad you shared it here. Definitely food for thought.