Conversation Starters for Picking up Girls


Several months ago-one of our loyal readers from North Brisbane dropped me an email asking if I could post some ideas and examples in relation to starting and maintaining engaging conversations with women.

Sounds like a reasonable useful request so I started brainstorming some ideas online only to find mainly cheesy everyday hum-drum boring as hell articles which I thought wouldn’t create any real value for my readers.

So instead, I approached some of my single friends to documents some of their experiences whilst they were out and about living the single life within various suburbs across Australia.

One thing that’s difficult to include in these case studies is the tone used when approaching women. So, before you even think about chatting up a girl at the club consider how your tone will come across. Visualise two equally handsome guys with two completely different voice tones. The first guy sounds like Donald Trump and second sounds like Pierce Brosnan – well not exactly the same but you get the idea.

Same good looks, same approach, two very contrasting voice tones? Guy number two definitely has the upper hand. Master your charm and style and you’re 90% there. Establishing a rapport with a single girl is not as complex and most men think.

All that is needed is a moderated level of interest to start building a connection. If the girl shows you a significant amount of interest she’ll do all the work. A moderate level of interest gives you a solid starting point but you’ll need to play your cards right to close out the deal.

My first case study was put together by John who lives at Newtown, Sydney. I sent John on an assignment to the World Bar in Darlinghurst and here’s what he recalls happening when he approached Misty.

John: I noticed you standing over here and just had to tell you your striking sense of style makes you stand out from the crowd.

Misty: Thank you that’s very flattering.

John: I’m John by the way, how’s your night so far?

Misty: I’m Misty, okay so far how’s your night?

John:  Yeah really good thanks, Sydney local or just passing by?

At this stage, fairly standard banter going on but the conversation has potential. You’ll want to further capture her interest so it’s time to start using more unique word choices.

Misty: Raised in Newcastle lived and worked in Surry Hills for the last eight years.

John: Ah okay, so you must know about all the secret places that only the locals know about?

Misty: Kind of I guess, been preoccupied with work lately though where are you from?

John: You mean right now or originally?

Misty: Right now.

Notice how John has escalated the conversation to put pressure on moving things forward. If john fails to add any value to the conversation she might start thinking about leaving. Since he’s acknowledged her and made her feel good about herself she’s going to feel obliged to show her own interest by asking John questions.

Even if Misty is showing signs of moderate interest here, John can use this kind of approach to structure the conversation so she starts chasing john. Notice how when Misty asks a question, John uses this to put the ball back in her court asking her to be more specific.

Given the ease of the request John is asking for, Misty can easily comply hence putting in further effort get answers out of John – here she is, chasing John again.

John: Well I’m definitely a local, haven’t always been, but I do live here now if that counts for anything.

Misty: How long have you lived here for where in Sydney are you from?

John: How long have I lived here? Been in Paddington for two and a half years before that I lived in Bondi for around five years. What do you do in Sydney?

Misty: I’m a paramedic.

John: Really wow! I bet you’ve seen some hairy situations?

John starts to hone-in a little on her emotional side, now that he has established an important aspect of her life.

Misty: There’s good and bad days but yea there’s definitely a very stressful element with this kind of work but I do love it.

John: Do you see yourself racing out saving people’s lives in the long-term what’s your five-  year plan?

Misty: I’m also a registered nurse so the plan is to eventually work in the public hospital system where things are slightly less chaotic but I’m also studying to become a veterinarian so who knows where I’ll end up (laughs).  What line of work are you in John?

Important: Establishing a connection with a woman often boils down to getting her to disclose information she views as personally significant.    

John: I’m an artist, I spend most of my time trying to be creative (laughs).

Misty: Such as?

John: Painting, photography the goal is to setup a studio in the next few months.

Misty: Really that’s so awesome I love photography.

See how she’s starting to form a bond with John – nice work John!

John: Do you really, do you have a creative eye?

Misty: Nah I’m pretty bad actually (laughs).

John: You can’t be that terrible (laughs), you’ll have to let me show you how to use a digital camera one day (laughs). Anything else you do that’s creative?

Instead of mocking her or making fun of Misty’s poor artistic talents, he sees a vulnerable side to her and recognizes that she sees John as more of an expert in this specific area. John wisely capitalizes on this opportunity laying the foundation for a possible first date offering to show her some pointers.

Misty: Nothing really.

John: Really? Nothing at all?

Misty: Nah sadly creativeness doesn’t come naturally.

John: I bet there’s times you’ve had to be creative being a paramedic and all?

Notice how John isn’t giving in, he’s trying to find a way to let her know she must be creative at something – implying that her job as a paramedic has plenty of creativity, he’s doing it to build her up to make her feel good about herself.

If you make the mistake of implying that the girl doesn’t meet a particular standard, you’ll lose the girl. Never let her fail, find a way to help her pass the test so she knows she’s on your side trying to help you to win her affections.  This is a great stage to be at.

Misty: I can draw a little does that count?

John: Absolutely, there’s thousands of ways you can be creative without even realising.

Misty: Are you an artist who makes money from your work?

John: Of course you mean you’ve never heard of me? (laughs) No actually, sadly it’s just a hobby I’m passionate about. I have a day job though to pay the bills I manage a local café nearby.

Misty: Oh cool.

John: To be honest it’s not much fun dealing with the general public, I’m hoping my photography business will take off eventually. Who wants to be slaving over customers when I could be painting your portrait (laughs).

Now Misty is starting find out a bit more about John, he’s not just some wannabe artist hedging all his bets on a dream. John defines himself as an artist being his passion, rather than a coffee shop manager. Artists are romantic, women see romantic men as perfect lovers.

Misty: (laughs) you better do a good job or the portrait won’t have time to dry before I tear it up (laughs).

John: (laughs) Seriously though, how is it that practically everyone trades their time for money? Actually I always wanted to be James Bond seducing beautiful women and killing the bad guys (laughs).

Misty: (laughs) I think that would really suit you maybe I can come along with you on some of your missions (laughs).

John: I can definitely picture you as my Bond girl.

Misty: Absolutely.

John: Although a bit of a shame Bond has a different girl in every movie I’m starting to fancy you. (laughs)

Her: (laughs)

John: What I could do is ask the movie writers to make a James Bond sequel so I can keep you as my Bond girl for two movies?

Her: (laughs)

John and Misty are really starting to bond here, John’s using roleplay portraying like he’s   hard to get, although still subtly helping her to pick him up. So now John has put himself in a position that he’s hard to get although remaining on her side nonetheless. She knows he’s not a pushover now but realises he’s helping her to succeed.

John: Hey there’s a spare seat over there come sit with me?

Misty: Okay

(off they go)

This was the perfect timing for John to step this up a bit. The pair are bonding perfectly thus she has no hesitation in committing to hanging out with John.

John: Misty tell me more about you, I hardly know anything about you?

John challenges Misty by further expressing interest in her, he wants to get to know her. This is a very commanding strategy John has introduced, it’s okay since he’s established the conversation and gained some trust. Taking a dominate approach puts Misty off guard a little so John will need to be nice and steer Misty in the right direction.

Misty: What would you like to know?

John: Are you a traveller or a stay at home person?

Misty: No not really travelled much at all, and you?

John: not a lot, now and then.

Misty: Where have you been so far?

John: Europe twice and went to Vegas last year. If you had a choice of places or countries to visit where would you go?

See how John doesn’t get carried away with bragging and big noting himself. She’s not a seasoned traveller and if John starts getting carried away with where he’s been and what he’s done, she’ll probably get bored stiff and could be a game changer.  Instead, he only very briefly touches on his own traveling experience and moves the spotlight back onto her.

Misty: Well…probably Europe

John: What’s your perfect Europe destination?

Misty: Well I love Spanish food Spain’s also very romantic, so Spain.

John: You like Spanish men huh?

Misty: (laughs) I heard they are great lovers (laughs)

John: Ay Caramba!

Misty: (Laughs)

John determines where Misty wants to go and maybe some of her fantasies and makes a little fun of her in a light-hearted joking way, intending to show her that he thinks she chases men.

John: I haven’t been to Spain yet, been to Paris and Italy which are also beautiful and romantic… honestly the food in Italy is spectacular, so many beautiful people of all ages too I bet you’d love it there.

Notice how the conversation is starting to develop into more meaningful and emotional way. Also see how John refrains from keeping the spot light on him. Instead, he focuses on how he fell in love with Italy which portrays him as a strong person who appreciates beauty. Women are instinctively aware that men who appreciate good food are typically great lovers, and John is starting to show this side of himself.

Misty: Italy sounds like my kind of place, I have to go there (laughs).

John: Hey, maybe we can make Italy our first mission for the next James Bond episode?

John reverts back to the earlier roleplay and includes Misty in the scenario rather than a simple “you should go there someday”  – which sounds dismissive and alienates John from the picture.

Misty: Which one Paris or Italy?

John: Sounds like you’d love Italy so let’s run with that. And besides, I doubt if the movie writers would let me have the same girl in both movies (laughs)

Misty: (Laughs)

John continues to play hard to get but is still on the same side as Misty.

John: So I’m gathering you’re not into travelling that much, what else do you do for fun and R&R?

Misty:  Umm nothing too exciting really, board games, reading, stuff like that.

John: Oh wow so not much of a thrill seeker? (laughs)

Misty: (Laughs)

John: Seriously though, everyone needs some action now and then.

Misty: Hmm, movies with friends, nice restaurants, bar hopping sometimes, dancing after a busy work week that’s kind of how my social life rolls I suppose.

John: Bar hopping, yep I can see that (laughs).

Misty: Yea once a month here and there.

John: You sure it’s once a month, once a week maybe?

Misty: (laughs) Nope clubbing isn’t too much of a regular thing.

John: I’m trying to believe you (laughs) you’re probably on a first name basis with every doorman in Sydney “Hey Misty you back again already”?

Misty: (laughs)

Misty and John are now just exchanging a little light -hearted banter just to keep the conversation rolling so things don’t start sounding too serious.

John: What else do you do there must be something you haven’t told me?

Misty: No nothing else really that springs to mind.

John: Right, cool okay.

Misty: How about you what do you do?

John: Mainly just chill on the weekends work during the day, do some photography maybe paint here and there when I can, to be honest my life is a bit boring I haven’t even had a near death experience lately (laughs).

Misty: (laughs) Well that’s a relief.

The near death experience comment John has thrown in was designed to make him sound more exciting than he actually is. If he finished up with “my life is boring” well that would sound, well, rather boring. As a result John keeps an air of excitement going.

John: Do you have family? Are they nearby?

The last conversation has run its course and not really going anywhere so John changes the tactics and digs a little deeper into her personal life.

Misty:  Mum lives in Chatswood Dad’s remarried and lives in Bronte in the Eastern Suburbs.

John: Any brothers or sisters?

Misty: Yep two brothers my youngest lives in Newcastle the oldest lives in Manly.

John: Manly! Great spot no shortage of eye candy and plastic boobs in Manly (laughs)

Misty: (laughs) for sure lots of beautiful people in Manly good people watching suburb (laughs).

John’s showing a bit of his cheeky side mentioning fake boobs but says it in a way that’s just a passing comment. Many girls are attracted to men who come across mildly cheeky, and it’s okay to be this way once you’ve established a rapport. If she’s the kind to take offence to light-hearted cheekiness chances are you’re barking up the wrong tree and might be time to cut your losses and move on.

Give or take, the conversation lasts around 10-15 minutes and by now he knows a bit about Misty. Depending on her circumstances John can potentially end up going home with Misty, even if she was only moderately interested at the beginning.

If you can engage a girl as successfully as John has in the above example, you should be able to land a 30% strike rate. Not bad going. Repeat this 4-6 times on a night out and you’ll be taking someone home. The conversation doesn’t need to be draw out and long-winded, keep things fast and fun.

P.S And by the way, John didn’t get to take Misty home, turns out she has a boyfriend. Seems John forgot to extract this key information from Misty at the start, a crucial over-sight. John won’t be making that mistake again. And neither should you.