Tag Archives: Flirting

How to flirt: Use this opener to start a conversation with women

Here is one of my favorite ways to start a flirtatious conversation with a group of women. This is tons of fun, and always gets a good response from the group.

I’ve used this during the day in a park, or in Union Square, and I’ve used it at night when I am out at bars. It is simple to use, and leaves a great opening to continue the conversation.

This works best with women in groups of 2 or 3, which is pretty common to see when you are out and about.

So what is this amazingly simple line to use?

“Hey guys, you know, I’m actually not sure which of you to flirt with first.”

That’s it. You can add to it, “You’re both so cute, I’m not sure which of you to flirt with first.”

You can change it up: “I’m not sure which of you I should hit on first. This is really a dilemma for me.”

This is a fun, flirtatious way to start the conversation.

You can then ask which of them is the best flirt, if one responds really well, tell the others that you are going to flirt with her, you can accuse them of being bad at flirting, and on and on and on.

A fun attitude makes this work. This is not a very serious way to start a conversation, so there is no reason to be too serious about it. A smile and upbeat attitude goes a long way.

Last weekend I approached a two women in a bar and used this opener, and one of them responded that we should play rock, paper, scissor to see who flirts with who. I’ll be stealing that from her.

Try this out, have some fun, and flirt with some women.

How To Flirt At Work

The internet disappoints me.

I did a google search for “how to flirt at work” and the most miserable results come up. If you believe the sources that Google says are the most relevant, all you need to do to make the ladies at your job swoon is to smile, give them compliments, and offer to do their work for them.


This stuff just doesn’t work. Sure, smiling and complimenting a woman may be a part of flirting, but it doesn’t really explain how to do it.

If you want to get an idea on how to actually flirt, read my article about role-playing and banter. That is, after all, what makes women like you.

There is more to flirtation than that, including teasing, playfulness, and innuendo, but banter is a huge part of what flirting actually is.

What about flirting with the women at work?

This is a question that always gets asked at the Art of Attraction workshop. Men want to know how to hit on that hot chick at work.

The simple answer: carefully and delicately.

Sexual harassment laws in our country being what they are, know the policy. Unwanted sexual advance or comment can be prosecuted. I am in no ways an expert. If you are going to flirt with girls at work, know the regulations that apply to you and your work environment. This post is written as infotainment, and is not advice. Don’t do something stupid.

If you are looking for an article about how to date women you work with, this isn’t it. I don’t date the women I work with. I don’t hook up with them. I don’t mess around with them. It makes life easier, and I don’t care how hot she is, there are plenty more women in the world that don’t have that particular complication attached.

But I do flirt with them.

I work with many women that I flirt with all the time. It keeps things fun. There are also many women at my day job that I don’t really flirt with. Some of them are receptive, and some are not. Some are kinda receptive, and some I can be more liberal with the flirtation.

Test the water before you dive

High octane flirtation does not always go over well. Also, you do not want to be the guy at work that hits on everything that breaths. Neither of these are good for your career, and your career should come before flirtation.

The hail mary banter or flirtation that may work well in the bars or clubs isn’t gonna be appropriate in the office. Out of place it can be too aggressive, and inappropriate. I test the waters out slowly, with a little flirtatious comment here and there, and I pay attention to how they react.

Throwing some roles into your banter is a good way to do this. Start with something fairly tame. You don’t want to start off by setting up roles of you as the love pirate and her as your slave. That is way overboard.

You can accuse a woman of being the office trouble maker, or set yourself up in the role of the boss, with her being one of your minions. The important thing is to do something that can be fun, but without a lot of sexual overtones to it. Then see if she plays along. If she plays along, laughs, smiles, and banters back, then it is a good sign that you can flirt with her a little more.

Once you know she is gonna respond to being flirted with, then you can slowly add a little more. By “slowly add a little more”, I mean over days and weeks. Not right away. There is no hurry.

Don’t touch too much

I am usually a very touchy feely flirt. I will be all over girls when I meet them, I put my arm around them, hold their hand, and so on. Not at work though. This is again, one of those things that I test out over time. When I do touch one of my coworkers, it is very little, gentle, quick, and as non-obtrusive as possible. I might touch their arm or shoulder, but that is about it. Anything more than that has to be with someone that I have a longtime relationship with, and we have worked that into the boundaries of what is acceptable.

Another way to not make any touching as awkward is to touch everybody, man or woman. This is the behavior of high status people by the way, and is something that good bosses will do. If you show that you are just a person that is comfortable touching people, you won’t so much be the weird guy that touches all the women.

Ramp things up after work

You can bump up the flirtation after work. Go out to happy hour with some of your coworkers, and you can bump up the level of your flirtation a bit. It is more appropriate in social situations because, well, it’s more appropriate in social situations.

You do need to still keep things appropriate, just because you’re not at work does not mean it is time to go hog wild. Even though you may not be in the office, you, and she, are still around co-workers, and their impression of you will be made as much after work as during work.

Many women aren’t going to want to be known as the office flirt, and for good reason. Keep this in mind. If you are making her uncomfortable with how much you are flirting you are missing the point.

The most important point

The most important thing to do if you are going to flirt with your co-workers is to pay attention to how they respond. A good response is smiles and laughs, and her flirting back. If you don’t get this type of response, pull it back.

Also keep in mind that it is possible to be playful without being too flirtatious. This is usually a matter of cutting out any sexual overtones in your flirtation and banter. You never want to make a woman you work with feel uncomfortable.

Take it slow, and have some fun. The more you flirt with your co-workers, the more you will get a sense for what is OK, and what is not. Flirting with your co-workers is a good way to keep things fun for you and her.

She Said, "That's What Makes Us Like You"

Last weekend the company I work for had our annual Holiday Party.

I got to dress up nice, hang out with friends from work, and drink a LOT of free wine. It was fantastic.

At some point in the night, I found myself at a table sitting with about 10 adorable women, some of whom I work with, some of them were friends along for the party.

So, yeah. I started flirting with them all.

I was bantering back and forth with a lot of these women, it was a true multitasking tour de force of flirtation. These women were pretty good at this too. Most of them know me pretty well, and know they can push things with me; they really giving me a hard time, in a fun, flirtatious way.

It was going on to the point that one of the ladies I work with who was walking by the table stops, and whispers to me, “you know they are flirting with you”. Like I didn’t know :)

At one point, our conversation turned towards dating, and boys meeting girls, and the women’s lament at men not knowing how to banter well. Keep in mind, this was their words, not mine. They complained that a lot of men they meet just don’t know how to have a fun, flirtatious, conversation of banter.

“That’s what makes us like you guys, you know”, one of my friends said to me. “We want you guys to banter with us”.

I told her I was going to quote her on that, and here, I’m doing just that.

Women WANT you to banter with them. They want to be able to have a fun conversation with you, and they want to like you. They want a reason to.

A few years ago, I wouldn’t have been able to sit at a table of ten women and be the center of attention. I wouldn’t have them flirting with me, and doing nice things like filling up my wine glass for me. I had to learn this, and practice it. Four years ago I would have felt like this was an impossible thing for me to do, but over the years I learned how. I was lucky enough to learn a LOT from Lance, and lucky enough to motivate myself to get out there and practice this skill with women.

If you think, “that sounds fun, but I’m not sure how to do that”, then Charismatic Conversations may be for you. This is a DVD set of Lance teaching everything he knows about banter and flirting with women. It has hours of examples and demonstrations, and actual women giving their feedback about their experience.

Click Here to go to the PickUp 101 website and learn more about it.

It's Not Easy Being Mean (And So Can You!)

I have been accused of being mean a few times recently.

I probably deserved it too 😉

Sometimes I really can’t help but to tease girls. They beg for mercy, but I have none. I am a dark, vengeful figure of flirtation.

Melodrama aside, you may have run into this. You are talking to a girl, having a flirtatious conversation, she is laughing, you are laughing, so you know, at the very least, she doesn’t hate you.

All of a sudden, she sticks out her finger, and accuses you of being mean.

Maybe she plays it up by looking hurt. Maybe she has a scornful look.

Are you going to break? Are you going to reassure her that you aren’t mean? You could tell her, “no, I’m a nice guy! I didn’t mean it!”

. . .

Remember, it’s not easy being mean.

I own my meanness. My meanitude.

I’m mean. I’m a mean machine.

But I’m nice and fun too!

Last weekend, when a girl told me I was mean, I looked at her, smiled, and said, “I know, but it’s so much fun.” She laughed, I laughed, and we moved on.

I don’t deny it, I have fun with it. I’m not really mean. I don’t say hurtful, spiteful things inspired by anger. If that is what mean means to you, then read this. If mean means having fun and teasing girls, and taking playful jabs at them, then by all means, have fun with this, and don’t deny it.

When you get accused, step up, and ask if there is an award, or tell her you learned from the best, or that you teach classes on the subject. Tell her it is part of your subtle charm. Just don’t deny it.

It's True: Flirting Is Meaningless!

Yup.  All that flirting?  Worthless.  No value.  It means nothing.

I haven’t lost my mind, and flirting is still fun and effective.

I hear stuff like this from men a lot:

“If I go talk to her and flirt with her she will know I like her”.

“How can I flirt with a girl if I don’t really know her?  I don’t know if I like her?”

“If I tell her she is cute she has to decide right then if she likes me”.

For a man, just seeing a woman is enough for us to like her, or at least be interested in her.  This can get blown way out of proportion, so we feel like we are committing ourselfs to this woman, just for talking to her.  It’s as if we are putting everything on the line and stating how much we are interested that something work out between us and this woman.  It can get so blown out of proportion that for a lot of men, they think flirting is tantamount to professing your love for a girl (yes, a bit of hyperbole).

The thing is, though, it’s not.

Flirting means none of these things.  There is absolutely no commitment that goes along with flirting.  It is fun, and sexy, and interesting, and may spark interest, but in no way does this mean anything about your relationship with this woman.  After a man and a woman flirt with each other, there is absolutely no commitment or expectation.

If you flirt with a girl, there is no risk.

You see, what flirting really is is just a fun conversation, with some hints of romance or sexiness.  The key word here is fun.  The fun that you have when you are flirting doesn’t mean that you have to do anything after you have that fun, or that there will be any expectations based on that fun.

In practical terms, this means that you can flirt with the girl in front of you in line at the grocery store, on the bus or subway, or next to you in a bar, and not worry about it.  Let it be what it is, which isn’t much.

Now I’m not saying that this doesn’t mean it won’t ever go anywhere, if you start flirting with a woman, you can continue to get to know here, and move things along.  That’s where the flirting leads, in general.  The flirting itself though, does not lead to these things.  It is just a fun way to interact with a woman.

You should never let any fear of what it might mean if you flirt with a woman to stop you from doing it.

Flirting is Infectious

I was getting my coffee this morning from the same little coffee kiosk that I always do, and of course, I flirted with Nikki, the girl who gives me my coffee, like I always do.

Then I noticed something. I had gotten my coffee, and I was waiting on the sidewalk next to the little coffee shop for my bagel. A lady who was waiting for her latte or whatever was sneaking glances over at me. Then another lady who was standing in line was shooting me glances. For a second I was thinking, “what is going on?”

Then I realized, “Oh, yeah. They like me.”

When you start acting more flirtatious with people, other people will notice. It carries over to other people. It effects the way you stand, hold yourself, walk and talk. Women notice, and it is attractive.

People will see that you have a little bit more lively attitude. They will see that you are having fun, and that you feel good. They will feel your smile.

Try it. Go flirt with the girl who gives you your coffee and watch how others notice.

Now knock that smile off your face.

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Approaching women and flirting with them in the middle of the day is just one of the things we teach in the three day long Daygame and the Art of Rapport workshop. It is three days on how to meet and connect with women in the situations you are in every day. Grocery shopping, at the bookstore, on the bus, and getting coffee. Check out more information.

Warning! Women May Impede Business

Smokin'I went into the bank today to sit down with a banker and get a couple questions answered about business bank accounts. Shouldn’t take long, about five minutes. Besides, I had some other errands to run. I have to get ink for my printer, check out laptop computers…

But then I sat down with my banker, and she was cute. Like, really cute. My five minutes of questions turned into a one hour conversation. We talked about the usual; dating, different cultures, and hot lesbian action.

I usually just don’t date the women that serve me professionally, like bartenders, bus drivers, bankers, and the like. I’d rather have a cute banker that loves me than an eventual ex-girlfriend that doesn’t. Hmm… this rule doesn’t make much sense to me right now.

The bad thing, I got none of my other goals accomplished!

Flirt Everywhere

(This one is for you, V)

It is important to be ready to flirt with anyone, anytime, anywhere. When I know that I am ready to flirt with a girl at a moments notice, I feel on top of the world. Electrified.

This is a little anecdote from last week. I was talking to one of my coaching clients, and I challenged him to approach a girl everyday with with the simple as syrup, “you’re cute”. I told him I would do it the next day too, so I headed out on my lunch break ready to flirt with some lucky woman.

After walking around, getting lunch, then walking around some more, I was getting disappointing, because I was really just not seeing any really cute women to flirt with.

Then I saw this adorable blonde in the Metreon. She was working at one of those little booths, selling a nail polish device or something. I walk up to her, she says, “Come here, I have something to show you”.

Immediately I replied, “You are way too cute to be selling me this. How about we just flirt together for the next few minutes?”

She giggled, I kept bantering, I vibed for a few minutes, but then she had to get back to work.

This interaction didn’t end up in a number, or a date, but that is OK. Flirting like that gets the blood flowing, gets your endorphins pumped, and makes you feel great.

Go out and flirt! Now!