First dates are filled with many opportunities to connect, but they’re also filled with just as many opportunities to misstep.

What one young dater thought was an admiring observation left her date running out in tears instead.

Read on for this tale of a nightmare first date.

AITA for listing out a woman’s insecurities?

A few days ago, I (18F) went on a date with “Elsie” (19F).

I had only met her briefly while volunteering and so most of it for me was just getting an idea of who I was talking to.

The two quickly dove into deeper topics.

She asked me what my experience in secondary school was like, and I mentioned that I used to get bullied.

Elsie said she used to get bullied for her appearance at school, particularly for her red hair.

So here’s where the foot starting going in mouth.

I said she was a perfect example of medieval western-European beauty standards.

She asked how, so I listed some – she’s very pale, has wavy fair/red hair, a high forehead, a long nose, etc.

It was clear this “compliment” didn’t resonate.

She stood up, almost in tears, and said I’d just pointed out all her insecurities.

She left before I could apologise properly (all I managed to say was “Oh, I’m sorry” with no further explanation).

She hasn’t contacted me since then, though I have tried to reach out.

She’s left wondering where she went wrong. She meant well, after all.

I’m definitely missing something, as I’ve been trying to work out why her reaction was so extreme when I thought I was complimenting her, but I can’t really piece it together (being autistic certainly has at least something to do with it).

AITA?

Your date leaving in tears is never a good sign.

What did Reddit think?

This redditor thinks the compliment definitely could have been phrased a bit more tactfully.

It’s clear this author needs some guidance, so this commenter tries to gently walk her through what she did wrong.

She could have said way fewer words and left the date on much better terms.

In her defense, she couldn’t perfectly anticipate her date’s insecurities.

She hoped her words would draw them closer, but instead, they tore them apart.

If you thought that was an interesting story, check this one out about a man who created a points system for his inheritance, and a family friend ends up getting almost all of it.