Self-deprecating jokes can be good – they show that you have a sense of humor about yourself and can take some good-natured ribbing.At the same time, there’s a difference between self-deprecating humor and having no self-esteem.and that is going to work against your desire to connect with the person you’re flirting with.
Some laughs, after all, aren’t because we find something funny.
Similarly, jokes that denigrate who a person is at their core – or who they want to be – are a bad idea.
You also don’t need to balance out every compliment with a tease.
Not every pull needs a push, especially after things are starting to heat up.
This helps mitigate the implications about the subject and makes it more acceptable.
You can also make jokes about people in ways that are actually compliments.
To go back to the “bad at their career” example, if someone their job, then those jokes are more likely to be well-received.
This is an area where practice and social calibration are going to be key.
There are always going to be things that we’re sensitive about, deep-seated insecurities that sit almost like raw wounds.
A joke, no matter how lovingly intended, at one of these areas, can end up causing pain, even if it gets a laugh at first.
In a more banter-y, antagonistic style of flirting, it’s the joking insult that covers the compliment without it.