[Quiz] The Art of Flirting: How to Bring More Playfulness & Connection into Your Dating Life

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What is flirting, and how do I get better at it? As a mindful dating coach, this is a common question I get asked. Flirting is an essential skill that fosters attraction, curiosity, and emotional connection. It’s a dance between authenticity and playfulness, a way to engage from a place of genuine interest rather than performance. If dating feels transactional, forced, or uncertain, refining your flirting skills can help bring more ease and fun into your interactions.

Many clients I’ve worked with initially thought that flirting meant being smooth, knowing the perfect witty line, or exuding effortless confidence. What we at Lovewell help them see is that effective flirting is about openness, attunement, and a willingness to take small social risks. We help clients let go of the pressure to impress and instead focus on being present and engaged so that attraction flow naturally.

While flirting may come naturally to some people, it is an art form and does not come naturally to everyone. However, with awareness, courage, and practice, anyone can learn to signal interest and magnetize more people to them.

What Gets in the Way of Flirting?

As you may have guessed, the fear of rejection is a big factor. In overcoming the fear of rejection, it's helpful to learn about a fun little bias known as the "Signal Amplification Bias."

Research shows that when we’re afraid of rejection, we tend to under-signal our romantic interest while imagining that we are over-signaling. A study by Vorauer, Cameron, Holmes, & Pearce (2003) found that people often believe they’re expressing attraction more clearly than they actually are. This means that even if you feel you’re being obvious, the other person might not realize it!

Practical Tip: Next time you’re flirting, push yourself to be just 10% more direct than feels natural. What feels bold to you may just register as normal, friendly interest to someone else.

Okay, How do I Figure out my Flirting Blind Spots?

If you scored low on flirting in our previous quiz, the following quiz will support you, just like mindful dating coaching can, to help you understand and begin to improve your flirting skills.

Below is a self-assessment to help you reflect on your flirting style. Take a moment to evaluate each category honestly. If you’re unsure, ask a trusted friend or coach (like an online relationship therapist in San Francisco—wink!) for feedback.

Flirting Self-Assessment

Green Lighting: Do You Signal Your Interest Clearly?

Do you initiate by smiling directly?
Do you make sustained eye contact?
Do you position yourself near someone you’re interested in—without being intrusive?
Do you engage by asking thoughtful, open-ended questions and responding with genuine curiosity?

Vulnerable Body Language: Does Your Presence Invite Connection?

Are your arms uncrossed, posture open, and is your body oriented toward the other person?
Do you maintain good eye contact without staring?
Does your energy feel relaxed, engaged, and playful?
Do you express enthusiasm through facial expressions and tone of voice?

Deep Listening: Do You Make Others Feel Heard & Understood?

Do you listen actively, reflecting back what someone shares rather than shifting the conversation to your own experiences?
Do you notice and remember details about the other person?
Do you ask follow-up questions to show you’re engaged in the conversation?

Playful, Confident Flirtation: Do You Show Up with Lightheartedness?

Do you allow humor and playfulness to emerge naturally?
Are you comfortable making lighthearted, teasing comments (in a kind and attuned way)?
Do you feel at ease initiating small, appropriate gestures of touch (like a playful tap on the arm)?
Do you use "feeling responses" like: “That’s such a sweet story” or “I love how you light up when you talk about that”?

Assertiveness: Do You Make Your Intentions Clear?

Do you express interest directly rather than hoping the other person will figure it out?
Do you use "I" statements to communicate desires, like "I'd love to see you again" or "I'd like to get to know you."?
Do you take small risks in signaling your attraction, i.e., lightly touching their arm during a laugh, sending a flirty text, or making eye contact just a little longer than usual?

No scoring necessary, just take time to look at the questions and notice your strengths and challenges. Make a plan to break down the roadblocks that prevent you from demonstrating some of these behaviors. Talk to a friend or coach, and do the following journal exercise.

Flirting Meditation & Journaling Exercise

Take a few moments to sit quietly, close your eyes, and bring to mind a memory where you felt truly excited about possibility—where you were bubbling with enthusiasm and couldn’t wait to express yourself. Let yourself absorb the feeling of that moment. Afterward, journal for a few minutes about how you can bring this energy into your dating interactions.

Bonus challenge: Make a list of activities that spark this feeling—whether it’s hiking, dancing, baking, or playing an instrument. Schedule a self-date this week to engage in something that lights you up. The more you nurture your own aliveness, the more magnetic you’ll be in dating.

Continue Your Dating Growth:

If you’d like deeper support in refining your dating approach, consider working with an online relationship therapist in San Francisco through Lovewell. We specialize in helping high-achieving professionals and sensitive seekers cultivate meaningful connections. Learn more at www.lovewellsf.com.

Happy flirting! ✨

Frequently Asked Questions (FAQs)

Q.1 What if I feel awkward or forced when I try to flirt?

A: Flirting isn’t about putting on an act—it’s about heightening the qualities of curiosity, playfulness, and interest that already exist in you. Start with simple things: making eye contact, smiling, and asking engaging questions.

Q.2 How do I know if someone is interested in me?

A: Look for reciprocity. If someone leans in, maintains eye contact, mirrors your body language, and engages in the conversation enthusiastically, they’re likely interested. If they seem distracted, give short responses, or avoid proximity, they might not be feeling the connection.

Q.3 I’m afraid of being too forward—how do I strike the right balance?

A: The key is attunement. Express interest, then pause to see how the other person responds. If they seem receptive, continue. If they don’t reciprocate, simply shift gears and engage in the conversation with warmth but without pressure.