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That's not even subtle. Why would anyone say someone was wearing an ugly dress to their first date?
Maybe if he said, "mint with chocolate? What's next, lemon tart flavoured marshmallow?" That's a nice insult about someone's taste, but it's a cute joke too. It also shows his range of imagination.
lol was only good when it meant lots of love
actually I take that back, “you did wear an ugly dress to our first date, [lots of love]” is worse than lol
The key difference between teasing and negging is this: one makes the subject feel good, while the other is a mild insult. You might tease your one friend who loves cooking about her elaborate preparations, but chances are that she loves that! That’s because it’s a compliment in disguise – you’re really saying “You put in effort to make delicious snacks for everybody, and that’s great.”
When it comes to flirting, you should follow the same guideline. Ask yourself this: is there any possible bad interpretation of what I’m about to say? Could it make her feel bad about herself?
Negging is calculated to make her feel slightly insecure, while teasing never has that effect. Joke about how she feels cold in all kinds of weather, don’t neg her about her ugly hoodie– or at least don’t be surprised when the conversation goes to a bad place after you do.
You: What’s your fave ice-cream flavor?
Her: Hmm, I’d have to think but- mint chocolate chip. Almost always.
You: Mint with chocolate? Oh God, I can’t trust your taste. But then again, you did wear an ugly dress to our first date, so I should’ve known lol.
This is a classic neg. You might think that adding a “lol” to the text takes the sting out of what you’re saying, but that’s not how it works! (Golden rule: a ‘lol’ can never negate an insult.)
Good luck, and remember to make sure both of you are having fun when you flirt!