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Avoid At All Cost: 15 Of The Most Awful Ways To Flirt With Someone

The art of flirting is a delicate endeavor where interest and respectful interactions are essential to success. However, there are unfortunate instances where individuals have employed misguided or inappropriate approaches that have only yielded awkward, uncomfortable, and even offensive outcomes. 

Invasive Compliments 

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Offering overly personal or objectifying compliments can make the person uncomfortable, demonstrate insincerity, and make it seem like you’re only after one thing.

Insensitive Jokes 

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Attempting humor that relies on offensive or inappropriate topics can quickly backfire, causing offense rather than laughter. When first meeting someone, you do not know their experiences and background. It’s best to leave the offensive stuff at home.

Aggressive Persistence 

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Continually pursuing someone after they’ve expressed disinterest can be seen as invasive and disrespectful of their boundaries. Stalkerish behavior will not give you a second or third shot with someone, so don’t do it.


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Playful banter that calls back to primary school flirting can be fun once you get to know someone. However, teasing or using derogatory nicknames will come across as disrespectful and lead to negative first impressions.

Flirting with Others

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Trying to make someone jealous by openly flirting with others can signal a lack of genuine interest and lead to hurt feelings. It actually looks like you are not interested enough in them, and many times, they will no longer be interested in you.

Excessive Touching 

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Invading personal space or touching without consent can make someone uncomfortable and create an unsafe environment. There’s nothing wrong with a physical embrace, provided it’s mutual and consensual.


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Fabricating stories or achievements to impress someone can lead to mistrust once the truth comes out. Lying is never the best way to impress someone.

Ignoring Boundaries 

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Disregarding personal boundaries can create discomfort and tension. If someone is giving off cues that the conversation has become too personal or they’re no longer engaged in the conversation, it’s best to end it.


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Making backhanded compliments or criticizing someone in an attempt to lower their self-esteem is manipulative and harmful and will not ultimately win over the person you’re trying to impress.

Playing Mind Games 

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Trying to manipulate someone’s emotions or create drama can undermine trust and authenticity. This can lead to toxic relationships and gaslighting that no one wants to be part of.

Ignoring Cues 

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Failing to notice or respect signals that the other person is uninterested can lead to awkward interactions. If they’re not responding or giving one-word answers, it’s best to move on.

Overusing Pickup Lines 

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Relying on clichéd pickup lines can come across as insincere and lack originality. Cheesy pickup lines will be laughed at behind your back; always be sincere in your approach.

One-Sided Conversations

Dominating the conversation without allowing the other person to share can feel dismissive and disinterested. Let the other person share their responses, listen to them, and engage after they’ve spoken. No one likes a know-it-all or someone who constantly butts into the conversation.

Arrogance & Overconfidence 

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Adopting a persona of exaggerated confidence online might not translate well in person and can appear inauthentic. Don’t lie about who you are. The person you meet will expect you to be the same way in person as you are online.

Ignoring Context 

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Flirting or hitting on someone in an inappropriate or serious situation can show a lack of social awareness and emotional intelligence. A funeral is not the place to find your next boyfriend or girlfriend.

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