Being from Boston (the city of sarcasm), I’ve always been a teaser at heart. Fortunately, it’s a critical aspect of flirting with women. When done well, it can create immense attraction and bring your conversation to the next level. It’s fun and shows her that you’re able to enjoy yourself so she can do the same.

To understand teasing you must first understand rapport…

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Rapport is when two people relate and connect with each other. As you talk about commonalities, share stories, and learn more about one another, you are building that rapport. These are typically safe conversations.

Flirting is the essence of creating tension and “breaking” rapport. You’re saying something a little edgy. She could tell you to go screw yourself and it’s potentially unsafe (but all great endeavors are risky to begin with!).

By nature, teasing is jokingly offensive. You’ve got to bust her balls, sarcastically criticize her, and make her feel vulnerable in a lighthearted way. Just keep in mind these five points:

• Make fun of her, not yourself. Self-deprecating, cynical, and negative humor might get a laugh but it won’t get you a date.
• Be expressive. Smile, use your hands to gesture, and vary your vocal tonality. At the end of playful phrases, inflect your voice upward. Get passionate and physical. Exaggerate and be absurd at times. Also…laugh with her, damn it!
• Ramp it up. Start with something less intense and get more personal as the interaction progresses. You couldsay something sexual very early on but if she’s not invested in you, it’s probably going to backfire.
• Have real conversation, too. Don’t tease her constantly, mix it up with more substantial or meaningful talk. Listen and avoid making fun of her when she’s telling you something serious. As you get to know her, tease less but never stop completely – the spirited attitude keeps her attracted.
• Flirt with everyone. Get in the habit of joking with women you meet daily. It’s innocent, harmless, and good practice. Plus, you’ll get a lot of numbers in the process. 

The following 10 examples aren’t only for girls at the bar. They can and should be used on dates, at parties, and occasionally over text.

Note: These teases are meant for bars and clubs when you have a good dynamic going with the girl. I wouldn’t get too forward when first meeting a woman during the day. Keep it to a couple light and non-sexual teases unless you take her on an instant date right then and there.

1. Give her a silly nickname. “You’re such a little brat/punk!” (smiling) “Don’t worry sweetie/babe/pumpkin/cupcake, everything will be just fine.” (jokingly comforting her) “I like that you’re always laughing, I’m officially calling you giggles.”
2. Point out something embarrassing or nerdy about her. “OMG, your dimples are so adorable.” “You have the cutest freckles on your nose.” If she does something clumsy, “This is why we can’t have nice things Mary!” “You’re such a nerd, where’s your pocket protector?”
3. Mimic or mock her. If she gets jokingly mad, huff at her and make an upset face. Playfully exaggerate her accent. Repeat her words back to her with your hands on your hips.
4. Challenge her. Thumb wrestle her. If you’re at a bar or club, have a silly dance off. “Please girl, I would so whoop your ass in X.” “First one to get served at the bar pays for the other’s drink.”
5. Treat her like a child. “Oh god, you’re so fired.” “I think somebody needs a timeout.” “Go sit over there and I’ll get you some crayons to draw with.” “Don’t make me spank you missy!” “I think you’re too young to be drinking that young lady.”
6. Roleplay with her. “You like Dr. Who? We’re officially best friends now.” (put your arm around her) “That’s it, we’re breaking up — I want my letterman jacket back!” “Where are we running away to for our honeymoon? I was thinking Fiji.” “I can’t believe we’ve been dating for three years now. Do you remember our first date?”
7. Stereotype her in a humorous way. “A Brooklyn girl, you packing heat?” “Uh oh, a lawyer…I got to be careful what I say around you.” “You’re from Tennessee? You must listen to songs about whiskey and tractors.” “Oooh a musician, can you write a love song about me?”
8. Tell her you wouldn’t get along. “I can’t believe you like Twilight, we can’t be friends anymore.” “We could never be friends, we’re both too stubborn.” “You are such bad news, I don’t know if we can hang out.” “You’re too nice, I would corrupt you.”
9. Disagree with something she said. Playfully turn your back to her. After she says she dislikes something say that you do like it or vice versa. Call her out for being rude or shallow. “No way, lame!” “Pssh, I disagree, there’s definitely good rap out there.”
10. Accuse her of hitting on you or being sexually aggressive. “Are you hitting on me?” “Get your mind out of the gutter!” “I see what you’re doing, your feminine wiles won’t work on me.” “No I will not hook up with you right here!” “Can you please stop checking out my ass?” “Don’t look at me like that, I’m not a piece of meat!” “Stop trying to seduce me, I know what you’re up to.” “Hey, stop thinking those dirty thoughts — we just met.”

Remember, teasing comes down to enjoying yourself and creating a playful dynamic. Use the examples as a guideline but start trying out your own ideas based on your personality.

You’ve got to take some chances — the guys who always play it safe usually go home alone.

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If you’re struggling to figure out how to get the teasing right, I don’t want you to feel like you have to do this alone. If you’d like a step-by-step, tailored approach to become more playful in your conversations, and more magnetically attractive to women, let’s have a free, 100% confidential consultation call (up to 30 minutes) to discuss how we can work together. Schedule your free strategy session here.