How to Flirt: Turn Everyday Moments into Opportunities for Connection

Flirting. It’s a word that can evoke a mix of excitement and anxiety. For some, it comes naturally, a playful dance of words and glances. For others, it feels like navigating a minefield, fraught with the fear of missteps and misinterpretations. But what if flirting wasn’t about being a smooth operator or mastering cheesy pick-up lines? What if it was simply about connecting with others, expressing interest, and having fun?

In an insightful conversation on the “Modern Love” podcast, comedian Amelia Dimoldenberg, known for her viral YouTube series “Chicken Shop Date,” delves into the often-anxious world of modern dating. While her show is framed around celebrity interviews disguised as dates, the underlying element is always flirtation. Amelia’s confident yet playful approach offers a fresh perspective on how we can approach interactions, not just in dating, but in everyday life, with a little more flirtatious energy. This isn’t about manipulation or insincerity, but about opening doors to connection and injecting a bit of lightheartedness into our interactions.

This guide will explore the art of flirting, drawing inspiration from Amelia’s perspectives and offering practical tips to help you become more comfortable and confident in expressing interest and creating engaging connections. We’ll move beyond the clichés and focus on genuine interaction, helping you understand How To Flirt in a way that feels authentic and fun for both you and the other person.

Understanding the Essence of Flirting

Before diving into techniques, it’s crucial to understand what flirting truly is. It’s not about being someone you’re not, or putting on an act. At its core, flirting is about:

Expressing Interest: Showing someone you find them interesting or attractive, whether romantically or simply as a person.
Creating Connection: Building a lighthearted and engaging interaction that goes beyond surface-level conversation.
Having Fun: Flirting should be enjoyable for both parties involved. It’s about playfulness and positive energy.
Building Confidence: Engaging in flirtatious behavior can actually boost your own confidence and make you feel more socially adept.

Amelia Dimoldenberg’s “Chicken Shop Date” embodies this essence perfectly. She creates a playful, slightly absurd scenario that allows for genuine personality to shine through. It’s not aggressive or overly serious; it’s light, humorous, and focused on creating a memorable interaction. This approach highlights that flirting doesn’t have to be high-pressure. It can be woven into everyday interactions, making them more engaging and enjoyable.

The Confidence Factor: Embracing Your Inner Flirt

One of the key takeaways from Amelia’s approach is the importance of confidence. As she mentions, “the confidence is key.” This doesn’t mean being arrogant or overbearing, but rather feeling comfortable in your own skin and projecting a positive self-image.

How to Cultivate Flirting Confidence:

Self-Acceptance: Recognize and appreciate your own positive qualities. As Amelia touches upon, “you know deep down that you’re hot, you’re great, you’re funny, you have great belief in yourself.” Tap into this inner belief.
Focus on Fun, Not Outcome: Shift your mindset from needing a specific result (like a date or relationship) to simply enjoying the interaction. Think of each flirtatious encounter as “a fun story for the group chat,” as Amelia suggests. This removes pressure and allows you to be more relaxed and natural.
Start Small and Practice: You don’t have to jump into intense flirting right away. Begin with small gestures like making eye contact, smiling, and initiating light conversation. Practice in low-stakes situations, like with baristas or shop assistants.
Body Language of Confidence: Stand tall, make eye contact, smile genuinely, and use open body language (uncrossed arms, relaxed posture). These non-verbal cues project confidence and approachability.
Positive Self-Talk: Challenge negative thoughts and replace them with positive affirmations. Remind yourself of your strengths and your worthiness of connection. Don’t let that “person on your shoulder that sometimes comes in and they tell you otherwise” win.

Just like Amelia, who acknowledges her past insecurities and the ongoing work of self-confidence, remember that building confidence is a journey. Be patient with yourself, celebrate small victories, and keep practicing.

Mastering the Art of Verbal Flirting

Words are powerful tools in the flirting arsenal. Verbal flirting is about engaging conversation, showing interest, and injecting playful banter.

Effective Verbal Flirting Techniques:

Initiate Conversation: Don’t wait for the other person to start. Ask open-ended questions that encourage more than just a yes/no answer. Relate your questions to the situation or environment.
- Instead of: “Do you come here often?”
- Try: “What brings you to this [coffee shop/event/place] today?” or “This place is great, have you tried the [specific item]?”
Active Listening and Engagement: Pay attention to what the other person is saying. Ask follow-up questions, show genuine interest in their responses, and remember details for later in the conversation.
- Example: If they mention they love hiking, you could say later, “You mentioned you enjoy hiking, I recently went on a great trail at [location], have you been there?”
Compliments (Done Right): Genuine compliments can be very effective, but they should be sincere and focused on personality or effort rather than just physical appearance (especially initially).
- Instead of: “You’re hot.” (Too direct and potentially objectifying)
- Try: “That’s a great perspective,” “You have a really infectious laugh,” or “I love your [item of clothing/accessory], it really suits you.”
Playful Banter and Teasing (Lightly): Lighthearted teasing, when done appropriately, can be a fun way to flirt. It shows confidence and playfulness. However, be mindful of boundaries and avoid anything that could be genuinely hurtful or offensive.
- Example: If they spill a little coffee, you could playfully say, “Careful there, you almost made a mess! Are you always this clumsy, or is it just my charming company?” (Delivered with a smile and light tone).
Humor and Wit: Sharing a laugh is a great way to connect. Use humor appropriately to lighten the mood and show your personality. Amelia’s “Chicken Shop Date” thrives on humor and witty banter.
- Share a funny anecdote, make an observational joke about the situation, or use self-deprecating humor (in moderation).
Subtle Innuendo (Use Sparingly and Read the Room): As Rachel Fields did in “The Five Stages of Ghosting Grief” essay with her “bench time” text, a touch of subtle innuendo can be flirtatious, but it’s crucial to gauge the other person’s comfort level and the context. Overdoing it can be off-putting.

Remember, authenticity is key in verbal flirting. Be yourself, let your personality shine through, and focus on creating a genuine connection through conversation.

Non-Verbal Flirting: Actions Speak Louder

While words are important, non-verbal cues often convey more than we realize. Body language, eye contact, and touch (when appropriate) are powerful tools in flirting.

Key Non-Verbal Flirting Cues:

Eye Contact: Making and holding eye contact is crucial. It signals interest and confidence. Don’t stare intensely, but maintain comfortable eye contact during conversation. “Prolonged eye contact” that is still natural is a strong flirtatious signal.
Smiling: A genuine smile is inviting and approachable. It signals warmth and positivity. Smile when you make eye contact and throughout your conversation.
Body Posture: Maintain open body language. Uncross your arms and legs, face the person you’re flirting with directly, and lean in slightly to show engagement.
Mirroring: Subtly mirroring the other person’s body language or gestures can create a sense of rapport and connection. However, avoid being too obvious or mimicking.
Touch (Use Cautiously and Respectfully): Appropriate and light touch can be a flirtatious signal, but it’s crucial to be mindful of boundaries and context. Start with non-invasive touches like a light touch on the arm or shoulder during conversation, and gauge the other person’s reaction. Avoid any touch that could be perceived as unwanted or inappropriate.
Proximity: Standing or sitting closer to someone can indicate interest. However, respect personal space and don’t invade their space too quickly.

Non-verbal cues are often subconscious, but being aware of them can significantly enhance your flirting skills. Projecting confidence, warmth, and interest through your body language can make you more approachable and attractive.

Flirting in Different Contexts: Online and In-Person

Flirting isn’t confined to just face-to-face interactions. In today’s world, online flirting is equally relevant. While the principles remain the same, the execution differs slightly.

Online Flirting:

Engaging Profiles: Your online dating profile or social media presence is your first impression. Use high-quality photos that show your personality, and write a bio that is interesting and engaging.
Thoughtful Opening Messages: Avoid generic “hey” messages. Personalize your opening message by referencing something specific from their profile.
- Example: “I saw you’re also a fan of [band/book/hobby]! What’s your favorite [song/chapter/aspect]?”
Use Emojis and GIFs (Sparingly): Emojis and GIFs can add playfulness and tone to your messages, but don’t overuse them.
Maintain Momentum: Keep the conversation flowing by asking questions, sharing your own experiences, and responding in a timely manner (without being overly eager).
Transition to In-Person (Eventually): The goal of online flirting is often to meet in person. Suggest a date or video call when the time feels right.

In-Person Flirting:

Context Matters: Be mindful of the situation. Flirting at a bar will be different from flirting at a library. Adjust your approach accordingly.
Use Your Surroundings: Comment on the environment, ask for recommendations, or use shared experiences to spark conversation.
Pay Attention to Cues: Observe the other person’s body language and verbal responses to gauge their interest level and adjust your flirting accordingly.
Don’t Be Afraid to Be Direct (but Respectful): In person, you can be slightly more direct in expressing interest, but always be respectful and avoid being pushy.

Regardless of the context, remember that genuine connection is the foundation of successful flirting.

Dealing with Rejection and Moving Forward

Not every flirtatious attempt will be successful, and that’s perfectly normal. Rejection is a part of life, and it’s crucial to develop resilience, as Amelia emphasizes.

Handling Rejection in Flirting:

Don’t Take it Personally: As Amelia wisely points out, “often it’s actually not about you.” There could be countless reasons why someone might not reciprocate your flirtation, and it rarely reflects on your worth.
Respect Their Decision: If someone isn’t interested, respect their decision and gracefully move on. Avoid being pushy or argumentative.
Learn from the Experience: Reflect on the interaction. Was there anything you could have done differently? But avoid overanalyzing or blaming yourself.
Maintain Your Confidence: Rejection can sting, but don’t let it crush your confidence. Remind yourself of your positive qualities and your worthiness of connection.
Focus on the Positive: Remember that you put yourself out there and took a chance. That’s a success in itself. Focus on the interactions that do go well and the connections you do make.
“Text Someone Else”: Taking Amelia’s practical advice, if you’re dwelling on a rejection, shift your focus to other connections. Engage with other people, whether romantically or platonically. “Having multiple options” can indeed ease the sting of rejection.

Resilience is key in dating and flirting. Just as Amelia describes her own journey, dating can be a “roller coaster of confidence.” Embrace the ups and downs, learn from each experience, and keep putting yourself out there.

Flirting for Connection and Joy

Ultimately, flirting should be a positive and enjoyable experience. It’s about connecting with others, expressing yourself, and adding a spark of fun to your interactions. Don’t get bogged down by anxieties or expectations. Embrace the playful nature of flirting and focus on creating genuine connections.

As Amelia encourages, “think of it as fun and more fun will happen.” Approach flirting with a sense of lightness, humor, and genuine interest in others, and you’ll find it becomes a natural and rewarding part of your social interactions. So go ahead, embrace your inner flirt, and turn everyday moments into opportunities for connection and joy!