Why Does Flirting Feel So Awkward?


Why Does Flirting Feel So Awkward?

Flirting can feel awkward for many reasons, but you can make it more comfortable by addressing common causes of discomfort and helpful strategies.
Why does flirting feel so awkward?

Flirting can often be a socially awkward experience for many people, leaving them feeling uncomfortable, unsure of themselves, and ultimately wondering “Why is it like this?

Why do I feel awkward when it comes to flirting?

The discomfort associated with flirting might stem from a fear of rejection, depending on specific outcomes, a desire for approval, or insecurities.

If any of these reasons speak to you, know that you can address these feelings head on and learn strategies to flirt more comfortably.

1. Fear of Rejection

One of the main reasons people feel awkward when flirting is the fear of rejection. Comparing yourself to others and questioning your attractiveness or worthiness can exacerbate this fear. Remember that everyone experiences rejection at some point, and it’s a natural part of the dating process.

How To Overcome Fear of Rejection

  • Focus on building self-confidence and self-esteem
  • Remember that rejection is a normal part of life and not a reflection of your worth
  • Practice self-compassion and self-love

2. Confronting Desire

Flirting often involves confronting your desire to be wanted by someone while acknowledging that the other person may not feel the same way. This can create an uncomfortable dynamic, making it difficult to engage in flirtatious behavior.

How To Address Confronting Desire

  • Be honest with yourself about your feelings and intentions
  • Accept that not everyone will share your feelings, and that’s okay
  • Focus on building genuine connections rather than seeking validation

3. Insincere Motives

People may feel uncomfortable when they don’t actually want to date or be romantically involved with the person they are flirting with, but do it out of a need for attention, approval, or boredom. If you find yourself doing this, you may want to explore why you do this and whether it’s part of a pattern that includes other toxic traits.

How To Manage Motivations

  • Be aware of your motivations and reasons for flirting with someone
  • Focus on building authentic connections with people you genuinely like
  • Practice self-awareness and mindfulness to better understand your emotions

4. Eye Contact

Maintaining eye contact with someone you don’t know well, especially someone you have a crush on, can be uncomfortable. However, eye contact is an essential part of nonverbal communication and can help establish a connection with the other person. It just might take some practice.

How To Improve Eye Contact

  • Practice making eye contact in everyday situations
  • Focus on one eye at a time to make it feel more natural
  • Remember to blink and look away occasionally to avoid staring

5. Vulnerability

Early in a relationship people may feel nervous about expressing their feelings and may feel too vulnerable to let the other person know they are interested. Embracing these feelings of vulnerability can lead to deeper connections and much more meaningful relationships.

How To Embrace Vulnerability

  • Remember that in relationships, vulnerability is a strength and not a weakness
  • Be open and honest about yourself, your feelings, and intentions
  • Practice self-compassion and self-acceptance

6. Insecurities

People may project their own insecurities onto others who try to flirt with them, making the interaction feel awkward. Recognizing and addressing personal insecurities can help improve flirting experiences and overall self-confidence.

How To Overcome Insecurities

  • Identify and challenge negative self-beliefs
  • Don’t rely on self deprecation or negative humor
  • Focus on personal growth and self-improvement

7. Misreading Social Cues

Another reason flirting can feel awkward is misreading social cues or not understanding the other person’s intentions. This can lead to confusion and discomfort during the interaction.

How To Improve Reading Social Cues

  • Pay attention to body language, facial expressions, and tone of voice
  • Practice active listening and asking clarifying questions with a trusted friend
  • Enroll in a social skills class to improve your ability to interpret cues correctly

Tips for Flirting Without Feeling Awkward

Flirting doesn’t have to be an awkward experience!

Use HumorLearning how to use humor early in conversation can help break the ice and make the interaction enjoyable.
Be AttentiveListen carefully to what the other person is saying, show interest by maintaining eye contact and nodding, and respond thoughtfully. Practice active listening by summarizing or reflecting on what they said.
Give Genuine ComplimentsCompliment the other person on something specific and genuine, such as their sense of humor or their outfit.
Be ConfidentConfidence is attractive, so stand tall, maintain eye contact, and speak clearly. If you’re feeling nervous, take a deep breath and remind yourself of your positive qualities.
Be OriginalAvoid using cliché pick-up lines and instead, try to engage in a genuine conversation that reflects your personality and interests. Being a good storyteller can also help in this regard.
Use Body LanguageNon-verbal cues can be powerful when flirting. Smile, maintain eye contact, and use open body language to show that you’re interested. Mirroring their behavior subtly can also create a sense of connection.
Keep the Tone Light and PGKeep the conversation light-hearted and avoid making inappropriate or offensive comments. Engaging in playful teasing can be an effective way to flirt if done appropriately.
Think Before You SpeakTake a moment to consider your words before speaking to avoid saying something that might be awkward or embarrassing.
Focus on Posture and ArmsStand up straight and avoid crossing your arms, as this can make you appear closed off or unapproachable.
Slow DownGive yourself time to process the conversation and respond thoughtfully, rather than rushing through your words.
Highlight Shared InterestsEngage in conversation about topics you both enjoy to establish a connection. Talking about mutual experiences can create a sense of intimacy and understanding.
Practice Mindful CommunicationPay attention to your words, breathing pattern, and body language to ensure they align with your genuine intentions.


Eric Waisman

Eric Waisman

Founding Instructor

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