The (second) time a waitress made a date awkward

Apparently there is one constant in my dating life (besides lots of failure, that is) -- there will always be an uncomfortable moment on the second date.

OK, so it's only happened to me twice.  But I can't help feeling like this might be a pattern.

Remember this story?  I nearly forgot about it until I experienced a bit of deja vu last week.

I met my date at a restaurant for our second date.  The conversation was good, the food was excellent, and we were having a good evening.  When it was time for the check, the waitress accidentally slid it next to me.  My date promptly reached for it and the waitress apologized.

If she had left then, the evening would have been only slightly awkward. But she wasn't done yet.

"I don't know why I did that. I can tell you two haven't been together long, but clearly she's the one in charge here," she said.

Nervous laughter.  Mostly from me.  He didn't seem to know how to respond.

"Just be sure to come back here for your engagement party," she said.

Blank stares.

Uh.

[source]

I decided there was no good way to navigate the waitress' comments, so I just dodged them altogether. I changed the subject back to what we'd been discussing previously.  The awkwardness didn't seem to linger, thank goodness, but those few moments were really touch and go.

Why does this keep happening to me? Have the dating gods not tortured me enough yet?

Has anyone else experienced awkwardness on a date thanks to a third party?  Please share!!