Thursday, January 2, 2014

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.


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!!


  1. That is just so strange!!! The only one I have is where I was sitting at the bar area at Chili's with my date. It was probably our 4th date maybe? And the people sitting across from us at the bar yelled over "so how long have you two been married because you definitely act like newlyweds?" I was mortified, but of course just laughed it off. They bought us drinks so it wasn't too bad. Just awkward.

  2. Why would anyone do that to someone who they can clearly see is on a date?! SO awkward!!! I don't think I've experienced that first hand but I've had my fair share of weird servers.

  3. All I can say is, 'wow!'. I wouldn't really know how to respond either maybe with an, 'umm...'. Very weird on the waitresses part.

    Happy to be a new follower :)

  4. What in the world??? That's SO bizarre.

  5. Oh man!! Way too awkward, she should not have stayed and kept talking!

  6. On my husband's and I's first date a group of guys asked me (when he was in the bathroom) if it was a first date or not. I said yes, and they yelled "I knew it! It looks like it is going well!" I guess they also talked to him while i was gone. At least they did it when we were separated. It would have been super awkward if we had been together. I can't believe that waitress! Is there a 3rd date planned?

  7. SO awkward! Congratulations've won the most intrusive comment of the week award! Glad you blogged about it ;)

  8. what? what was she thinking!? she should have done a little less talky and a little more shut the hell up.

    Vodka and Soda


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