How many times have you felt that a conversation with a guy you really liked didn’t go well. Maybe he seemed bored with what you were talking about? As soon you ran out of commonalities, an awkward silence set in? His eyes scanned the room like he was looking for someone else to talk to? Or after his friends interrupted he never asked you to continue your story?

He didn’t ask for you phone number and you were more than a little disappointed when he walked away. Most likely you concocted rejection excuses. He probably had a girlfriend. Maybe he was gay? Maybe his goldfish just died and he’s having a really hard time coming to terms with its passing?

But let’s be honest with ourselves. He didn’t feel any chemistry with you.

And let me share with you something else. You could have easily spurred attraction and had the guy begging for your phone number. Your future with a guy hinges on your first impression. Flirting makes or breaks your conversation with a guy. There’s a good chance that the guy was attracted to you, you just needed to know how to boost his curiosity and keep him interested.

The good news is I wrote an entire book called Real Men In on the subject of meeting and attracting the men you want using what I call the 3 L Method. In the book I take you on a wild ride through the 3 steps for attracting men: Lure, Lust and Love. Flirting is the essential ingredient to every step along the way. Unfortunately so many women don’t know when and how to turn up the heat. They miss out on opportunities with great guys, because they didn’t correctly light the ‘spark.’

When researching for the book, I set out to find out why some guys felt chemistry with certain girls and why those same guys didn’t feel chemistry with other girls. I hoped to discover how a woman could create a more positive interaction. How she could ignite attraction.

I started out by asking a variety of guys why they weren’t interested in a girl when first meeting her and here were some of their answers:

            “I don’t know? I guess she was nice. Just nothing there.”

            “I met this chick that was really hot and I thought, cool, I think I could dig this girl. But then she started talking. All she did was complain about her apartment and her job and then her parents. I thought, my god: isn’t this what therapists are for?”

            “Man this girl was boring. All she talked about was her job. On and on. I get it. You work in digital strategy.”

            “It’s cool that she snowboarded. But it was like she was my buddy. We could probably hang as friends, you know?”

What all these guys have in common is that they met girls they were initially attracted to, yet, within a few minutes they were disappointed because there was no spark. Bored, they ended the conversation.

Attraction is caused by short, memorable moments. Not by long, drawn out conversations.

In the process of meeting someone new, we save time by screening them. We make small snap judgments, assumptions of who we think they are. During these first moments is when attraction is formed. It’s at this point we determine whether the conversation continues or someone takes a hike. If you bore a guy to tears in the first few minutes, he may imagine your first date together – you jabbering on and on while he pinches his arm to prevent himself from falling into a narcoleptic stupor. No one wants to waste their time.

Attraction is caused by short, memorable moments. Not by long, drawn out conversations. Boosting your desirability in a guy’s eyes only takes a few words and expressions. To hook a guy, keep things brief and direct, but fun.


So how can you do this?

Start by alternating serious questions with good mannered teasing. Teasing means reprimanding him, daring him, poking him, touching him, calling him nicknames and talking back. Basically, the same rules from middle school apply. If you like someone: you make fun of them. Go in with the attitude, “I’m watching you, Mister. I’m not letting you get away with anything.” Toss in some subtle body language. Flip the conversation from boring to sarcastic with the tone of your voice. Now you’re not just talking with a guy, you’re flirting.

So what’s flirting?

“Flirting is a behavior leading another to believe that sexual intimacy is possible, while preventing that possibility from becoming a certainty.” – Milan Kundera

A Czech author named Milan Kundera has a great definition from his book The Unbearable Lightness of Being. “Flirting is a behavior leading another to believe that sexual intimacy is possible, while preventing that possibility from becoming a certainty.” In other words, flirting is a promise of sexual intercourse without a guarantee.

So how do you allude to Milan Kundera’s promise of sexual intercourse? How do you make a conversation fun? Here’s a preview of a few tips on how to use flirting to keep a conversation rolling from my course Real Men In.


Answer Standard Questions with a Playful Answer

If you live in LA, inevitably, you bring up the traffic. In Wisconsin, conversation revolves around the snow. In Massachusetts, they rely on the asshole drivers. New York, apartment rent. Small talk is a snooze. But we all fall into the trap when we first meet someone. So how do you balance the small talk and interview questions with humor successfully?           

Think of famous comedians like Louis C.K., Aziz Ansari or Larry David. Their material might be based on everyday activities but they make mundane things funny by doing or saying something unexpected. Use their technique. When the conversation stalls, inject a dose of playfulness, humor, or sarcasm.

A good time to start is when a guy asks the first standard get-to-know-you question. He’s lobbing the question your way, expecting a standard, ho-hum response. Let’s use my friend Chelsea. Here’s her standard answers:


Him: What’s your name?                                

Chelsea: Chelsea


Him: Where do you live?                                

Chelsea: Seattle, Washington


Him: What do you do?                                    

Chelsea: I’m a human resources manager


Yep. I’d make a quick break for it too. With answers like these there’s not much to elaborate on. There’s a small shot they might delve into some fascinating material about his 401k. Maybe transition into a riveting weather discussion. Of course, he isn’t going to feel any chemistry. Chelsea has given him nothing to play off of.

Back-and-forth playful banter creates attraction. To create that zing, we need to offer up something he can hit back into play. What if Chelsea answered creatively and with a little humor? We’re going to create what I call a conversational hook.


Him: What’s your name?                               

Chelsea: My real name or my alter ego?


Him: Where do you live?                              

Chelsea: You know, they usually let me cozy up on the pool table. I’ll use napkins as a blanket. I’ll make a great little breakfast off those little cocktail olives and cherries. I’m really lucky – I mean I have a jukebox and dart board and soda that comes out of a gun. All. Right. Here. I mean, do you have that?


Him: What do you do?                                  

Chelsea: I fall down a lot at very inopportune times.

Chelsea: I take in all the unwanted Beanie Babies. It’s not fair that they don’t have homes after the craze ended.

Chelsea: I’m currently in my fourth year studying to be a zombie.


Alright, now we have something to work with.

More, your playful answers need a real anecdote behind them. For example, if Chelsea used one of her endearing flaws, like the fact that her bed is entirely hidden under a mound of stuffed animals, she could transition into an embarrassing story. Even with a short anecdote, she’s already in far more interesting conversation territory.

This strategy might sound fake or manufactured. But you’re not lying. You’re joking around and spinning true stories from your life to make them more interesting. For example, Chelsea is a regular at the bar, she’s clumsy, collects Beanie Babies and is obsessed with The Walking Dead.

I helped my friend Cindy with this exercise. Cindy works as a digital project manager. All day she’s hounding clients for assets, nagging web developers, assuring deadlines are met, and basically being the Xanax for a boss who refuses to take any. 

Cindy’s a successful gal but a digital project manager doesn’t exactly prompt a series of titillating questions and spark rapt desire. After analyzing her hobbies and interests, I suggested she approach things at a different angle.

Recently, Cindy took up flying lessons. Now, flying takes guts. I associate flying with movies starring Tom Cruise. It comes down to the fact that flying isn’t basket weaving. On her last lesson, her instructor cut the power, stalled the plane, and as they free fell to their ultimate demise, explained with the calmness of a monk how to regain control the plane. As one of those people who hold their breath at takeoff and only relish flying for the free Bischoff crackers on Delta flights, this does not sound like how I’d choose to spend my Tuesday and Thursday mornings.

So when a hypothetical hot guy asks Cindy, “What do you do?”, I coached Cindy. “I’m a semi professional pilot, well, that is if I don’t kill myself.”

When you deliver a conversational hook, such as this one, with a hint of sarcasm, it gives the guy something to work with. To begin with, Cindy’s introducing an interesting topic to lead off the conversation. Again, flying isn’t coin collecting. A guy is bound to have a few inquiries. Secondly, she’s transformed herself from boring office drone to Amelia Earhart flying a frickin’ propeller plane. Cindy can cover her daily grind later, once she and the hottie have established something between them. Third, she’s made a joke and promoted a further explanation. When she says, “If I don’t kill myself,” she’s admitting she’s not very good yet at flying. You can bet your bootie a guy will want to know why. Intrigue a guy and he’s going to want to know more. By throwing him for a loop with a conversational hook, she’s gone from average to interesting and attractive.

Now imagine what it would be like if you used this flirting technique on the hottie at the party that most women don’t think they have a chance with and he was begging for your phone number?


Mix Serious With Fun. Stir Until Combined.

When you meet a guy you like, you want to get to know him. There’s a good chance you’ll start asking him common questions about himself, his career, his life, his family.     

I call this trap the Comfort Zone. Sure, you might be getting to know a guy by talking about everyday stuff, but it’s a trap because you’re making yourself LESS interesting by acting predictable. Guys want to be with the girl who is laughing, having fun, and flirting. Not the one who’s conducting a job interview.

I realize it’s tempting to talk about these regular things because they feel safe. It’s the way you’re used to talking with your colleagues, friends, or family. But you’re not talking with your brother here. You’re creating a memorable first impression with a cute guy. Such that you don’t want to come off as normal. You want to stand out. Avoid the Comfort Zone by surprising him.

What are some ways we can surprise him?

First, don’t just accept compliments but instead say something that he can use and play back.

For example, when a guy tells me he likes my large X-shaped cocktail ring, I could reply, with a simple, “Thanks!” Accepting the compliment with a bland, one word answer, the topic dies a painful, boring death. Instead, add some spice. I could reply with, “Yeah, you better watch out, I like to brand guys with it,” and take my fist and lightly jab his arm like I am stamping the X symbol on his bicep. I’m flirting and creating sexual tension by using his compliment as a jumping off point for playful banter.

Constantly challenge men. Remember my statement from earlier, “I’m not letting you get away with anything, Mister.” When you talk with a guy, repeat this statement in your head. It will put you in a fired up mood.

Let’s look at an example. I met Kent in the beer line at a music festival.


            image_200x300_16Within the first minute of our conversation Kent says,“I work in computers. Boring stuff.”

            From the get-go Kent stated aloud that his career was boring and he didn’t want to talk about it. I could have ignored his warning and leapt right in, asking what his job title is, where he works, which route through rush hour he takes to work…blah, blah, blah.

            This kind of conversation is reserved for lunch with grandma.

            I definitely didn’t want to be in grandma turf. I didn’t even want to be the girl he met last night. I wanted to be unique, one-of-a-kind. Memorable. Attractive.

            So I challenged him. My body language was confrontational. I stood arms akimbo and jutted out my chin. My tone dared him, “Computers huh?”

            “You like computers?” His questioning intonation told me he was wondering if I’d contest.

            I joked, “No, I like typewriters. We’re past the eighties, it’s safe to say everyone likes computers.”

            It’s a good thing I didn’t answer politely with a real question like:“What do you do with computers?” That would have sent me on a one-way trip to the comfort zone.

            Then I reverted right back to flirting. “Let me guess: you either fight hackers or you are a hacker.”

            I delved into interesting territory. I declared him a hero or a naughty villain.

            “I’m definitely a hacker.” Kent replied.

            I added to the interesting fantasy role I created for him,“I hope you’re a super villain hacker. Super villains always get the cool toys, like lasers.”


By role-playing, I turned our conversation into a game. Sure, we could have talked the finer points of internet code. Rather, I transformed the boring computer geek into a super villain with lasers. And who wouldn’t want to be a super villain with lasers, I ask you? Since Kent played along, our conversation knew no bounds.

 Keep this in mind: if you ask a boring question, you’ll get a boring response. If you ask an interesting question, you’ll get an interesting response. 

To keep a man’s interest, I don’t let a conversation get too serious too soon. One way to do this is to alternate between real questions and playful ones. Keep this in mind: if you ask a boring question, you’ll get a boring response. If you ask an interesting question, you’ll get an interesting response. So here’s a preview of challenging and fun questions guaranteed to NOT put him to sleep:


1.) When you were little, what did you want to be when you grew up?

2.) If you could time travel anywhere, right now, where would you go?

3.) What’s your strategy in case of a zombie apocalypse?

4.) If you won the lottery, what’s the first thing you’d do?

5.) If you could have any type of pet, what would it be? (extra points if he says a fantasy creature like a dinosaur or wood nymph. Unicorn…boom.. you got me.)


Questions like these allow a guy to open up. They smoothly blend the fun and flirty with the personal and intellectual stuff. Shaking together a concoction like this, you’re making yourself a cocktail of irresistibility.

One word of caution: while it’s important to have fun with your questions, make sure you insert them naturally in a conversation. Pace your questions and focus on how you phrase them. You don’t want to bombard him with a series of out of the blue inquiries. It will seem awkward if you’re moving from discussing where you grew up to randomly planning for the eminent zombie take over.


Learn more ways to ratchet up attraction and keep a man in hot pursuit in my book Real Men In. In it you’ll learn more on:

  • Approaching a man with my 5 Openers Method
  • Using body language
  • Withholding rewards
  • Giving a little and pulling back, a technique called Push Pull to ratchet up attraction
  • Sexual innuendos
  • 3 key ways to stand out


And I’ll discuss what turns a man off and kills attraction so you’ll know what to avoid.

Ask yourself this: what if used my techniques and one more good catch asked you out? Would it be worth it? What are the consequences of doing nothing? If you do something today I can pretty much guarantee your dating success will get better.