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Over the last year plus, I’ve given you a lot of tips on where to meet new and interesting singles, how to make the approach, how to banter and flirt, how to get their number and what to do when you’ve got it. Today, I want to talk to you about how to put it all together. And one of the best ways of doing this is to break down a successful approach… one from my dating past, in fact.
Much like with the tale of the Lonely Soldier Girl, the Doc is taking his turn on the examining table and putting one of his own experiences in making a completely cold approach – that is, going up and meeting a stranger I have no social connection with – under the microscope. But instead of the traditional Post-Mortem, we’re going to be looking at what went right and why… and what you could take away from this.
Now to be sure: this isn’t one the most dramatic1 or complicated2 cold approach I’ve had; in fact, it’s fairly low-key and uneventful. This is why I chose it: because nine times out of ten, meeting someone new isn’t a matter of high drama; it’s just knowing how to be as charming and interesting a person as you can be. Almost every time I’ve met someone, got their number and eventually went on a date with her, the process followed a pattern similar to this one.
Some obligatory ass-covering: this is being posted with the approval of all involved parties. Certain details have been changed to protect the innocent3 and the guilty4.
So with that in mind, I give you the tale of the Reverse Cowgirl.
The Setup
Back in my wilder days – before I burned out on the bar scene – I spent a lot of time hitting the bars downtown. I used to go out two, three, sometimes four nights a week with a group of friends to hit a couple of our favorite bars for some good times and bad decisions. We were a crew of guys mostly out to have fun and meet women; if we got laid, great, otherwise as long as we were enjoying ourselves, it was all good. Usually Friday nights meant that we would meet up at this one particular bar for a drink and some general bonhomie – what we’d been up to that week, talking food, TV, women… your basic male-bonding stuff – before heading off to see what the night would bring.
“Isn’t that the monolith from 2001??”
This particular night – a Friday – I was feeling especially good. I’d just finished a major project and was looking to celebrate. I ended up downtown early with an hour to kill, so I decided to hang loose at a coffeehouse in the area and chat with anyone who seemed like they might be interesting to talk to until my buddies made it down.
Analysis:
This may seem somewhat inconsequential, but it’s actually surprisingly important when it comes to meeting people. Your attitude has a lot to do with success; if you’re in a good mood and with an attitude of “I’m out to enjoy myself”, you’re going to find that more people are interested in talking to you than if you come across as someone on a mission to get laid – or worse, someone who’s pissy, sullen or otherwise in a shitty mood.
In addition, chatting with random friendly strangers can be a good way to get into social mode – think of it as the social equivalent of stretching and doing warm-up exercises before a run – and get into a more outgoing headspace.
The Girl
I noticed April5 within seconds of the barrista handing me my latte. It was the cowboy hat that caught my attention; Austin isn’t known for a preponderance of urban cowboys or western attire, so anyone wearing a cowboy hat is going to stand out by default. More interestingly, it looked as though it had been screen-printed; it had a design reminiscent of an Old School Americana tattoo on the crown. The hat alone was enough to make me want to say “hello” – it was legitimately the coolest hat I’d seen in quite some time. The fact that the woman wearing it was cute – wavy shoulder length sandy-blonde hair, a black tanktop, jeans – certainly helped.
Oh god, I’m not going to have to pretend to like country music, am I?
She didn’t seem to be my usual type to be sure, but she was definitely someone I’d be interested in at least talking to for a little before I left to meet my friends. As I made a quick assessment – she was sitting by herself at a two-top table in a fairly well-trafficked part of the coffeehouse, a single large coffee, looking up occasionally at the crowd, but not apparently looking for anyone – I noticed that she was doing quick pencil studies in a spiral-bound sketchbook.
That cinched it; I’d always had success with arty types. I was an artist myself, and I was always interested in seeing other people’s work, especially sketches.
Analysis
When you’re approaching someone – assuming you’re following the 3 second rule – a quick look around is worth it to determine several things. In my case, I wanted to make sure I wasn’t about to intrude where I wasn’t wanted. First: was she there by herself or with friends? Approaching one person by herself is slightly different from a group, especially when they’re seated; you need to be careful not to be creepy by accident. Since she was at a small table, I didn’t want to steal somebody’s seat if they were at the bar or in the bathroom… and I also didn’t want to be interrupted by an annoyed friend (or date) if it came to that. I also wanted to gauge whether or not she was in “don’t bother me mode” – seated in a corner or away from the main traffic area, eyes locked on her sketchbook, headphones on or otherwise giving off “not interested” vibes. I’d done my share of sketching-in-a-public-place-to-meet-people and I recognized the signs.
“Oh bullshit, you didn’t get past counting coffee cups on the table and hoped for the best.”
As an aside: I don’t recommend this as a way of trying to meet people.
If all of this sounds a little like I’m trying to say I have super-Terminator Vision or some Sherlock-esque ability to notice insane little details and deduce facts from them… well, I don’t. Most of what I was doing was looking for really obvious things; by this point I had made (and fucked up) enough approaches to have learned what to look for via a long process of trial and error. I’ve lost track of how many times I ended up getting shot down because I didn’t notice an engagement ring or wedding band. This is one more reason why I advocate keeping detailed journals and documenting your progress; it helps you learn to recognize patterns.
The fact that she was sketching gave me an instant point of commonality: we were both artists. Even if it turned out that she (or I, for that matter) wasn’t interested, I was willing to bet that I’d enjoy talking to her; I legitimately like meeting artistic people, even if I’m not hoping to get their phone number.
Ironically, I would later find out that she was actually trying to catch the eye of a guy in the corner who was also drawing. Go figure.
The Approach
I walked up to the far corner of her table. “Hey, can I see what you’re drawing?” I asked. She looked up – she didn’t notice me as I’d walked over – and I smiled. I nodded at her sketchbook. “Is it ok if I look at your sketch? I know some people don’t like it when somebody stares over their shoulder when they’re in the zone…”
“Sure,” she said and leaned away from the sketchbook.
“Mind if I…?”
I pulled an empty chair from an adjacent table and sat perpendicular to her. “I’ve only got a couple minutes before I have to meet up with some folks,” I said as I put my latte down. The figurework was loose and sketchy, but the clothing was surprisingly detailed. “Wow,” I said, “I really like the way you do cloth. Drapery drives me fucking nuts.”
“Yeah, me too,” she said. ” Makes me wish I was only doing underwear. Are you an artist?”
God I loved questions like that. They might as well be asking “Hey, would you like this opportunity to show off and humblebrag a little?” I wasn’t the world’s greatest painter by any stretch of the imagination – in fact, I eventually quit painting and took up writing instead – but I was pretty good and I’d been in a few local gallery shows. I definitely had enough skill to come up with some visually striking pictures – especially since I was working digitally at that point. Photoshop lets you correct for many, many sins. This was shortly after the iPhone had been released, so I made a point of having copies of my latest paintings stored in the photo app for just such occasions.
“Hey, first things first. You show me yours and I’ll show you mine.” She laughed. “I’m Harris,” I said. “April,” she said, shaking my hand before flipping her sketchbook back to the first page. April was studying fashion design with an eye towards interesting prints and unusual dress designs and accessories. “That explains the hat,” I said.
“Hey, don’t knock the hat!” she said in mock outrage. “It’s my one concession to being a Texan,”
“Does it get you a lot of guys asking if you could hog-tie ‘em?”
Smooth.
“Wow, that’s the best innuendo you could some up with?” she asked with a grin. I rolled my eyes at her.
“Heard it before, huh?” She nodded. “That’s what I get for going for the low-hanging fruit.”
“So now I’m low-hanging fruit?”
“I notice you didn’t answer my question,” I replied.
“No, but you’d be amazed how many guys choke when I tell them I prefer to ride bareback.”
Oh yeah. I liked this one.
“You mind?” She handed me the hat. It was a gift from her roommate, who worked in a hat store out by UT campus. I was surprised to see that it’d been hand-painted. I was impressed; I was never as good with physical media as I was with Photoshop, and I would’ve loved to be able to paint something like that.
I flipped the hat around and put it back on her, backwards.
“Here you go. Now you can tell them you’re into reverse cowgirl.” She broke into peals of surprised laughter as I pulled out my phone to show her some of my paintings. She scooted closer to me and leaned in and I put my hand on her back. “You realize I’m going to have to call you ‘Cowgirl’ from now on. That’s totally your name to me now,” I said.
“Jerk,” she snorted and smacked me on the shoulder.
Analysis
April was fairly intent on her sketch by this point, which meant that she wouldn’t necessarily see me when I walked up. I made a point of approaching from the front at a slight angle rather than from the side or behind her for just that reason – it meant that she was much more likely to see me coming over through peripheral vision – and keeping the table between us. This way I was less likely to startle her or provoke an immediate sense of threat when I would say “Hey”.
Similarly, when coming up to someone who’s seated, it’s important to sit down as soon as possible – otherwise you end up coming across as looming over them, which can creep them out. It also carries the context that you’re seeking their approval and attention. Think of it in the context of a boss and employee – the boss is seated at his desk while the employee is standing nervously in front of him. The seated person is in the comfortable position while you’re standing; the body language and position sets you up as being the one seeking the other’s approval. Sitting down puts you at an equal level.
Mentioning that I only had a few minutes also helped put her at her ease; it meant that if I was a creep or a jackass, she was only going to have to put up with me for a short amount of time before I had to get up and leave… and if I didn’t, she had a built in escape clause; an icy “Didn’t you say you had somewhere to be?” is a good way of telling people to fuck off when they’ve worn out their welcome. If we were having a good time, I could either elect to stay and keep the emotional momentum going, or leave on an emotional high-note and call later… assuming I got her number.
I was genuinely interested in looking at her sketches, which made talking to her easier; I wasn’t giving the “I’m here to pick you up” vibe, I was just a guy who was interested in talking about something we clearly had in common. Having my own work readily at hand via the iPhone meant that we could compare notes and I could brag a little as well as back up my claims – I’ve known lots of guys who claim to be photographers or DJs but have never touched a camera or a turntable in their lives. Lots of folks will claim to have a cooler job than they really do in order to borrow some of that coolness for themselves.
Her response to my (admittedly lame) joke about the hat gave me a good indication that she was interested in flirting; she called attention to it without shutting me down or telling me that it was inappropriate. Coming back with a more overtly sexual reference also gave me a good indication of her sense of humor and what level of edginess I could get away with, as seen in her response to the “reverse cowgirl” joke. If she hadn’t made a similar joke back to me, I probably would have kept things dialed back a little until I had a better sense of how interested she was. As it was, when she leaned in to look at my phone – as opposed to taking it from me and flipping through it on her own – I knew she was getting into me; I had good reason to assume that she would be cool with my touching her.
Giving her a cute nickname is a good way of not only keeping a shorthand of who she was if I got her number – you’d be surprised at how quickly names can blur – but also of cementing me in her mind. If I called her up and said “Hey Cowgirl this is Harry…” she is much more likely to remember me – and the fun she had with me – than if I said “hey, this is Harry, I don’t know if you remember me but I talked to you about your sketches…”
The Close6
As much fun as I was having talking to April, I really wasn’t kidding when I said that I only had a few minutes before I had to meet my friends. We were vibing and I was definitely interested in her, but I already had plans and I didn’t feel right just blowing them off; I also didn’t know April well enough to invite her to come with me on what was ostensibly a guy’s night. Plus, with her sketchbooks and coffee, she seemed fairly well settled in for the immediate future. I pulled one of my business cards out of my wallet – I was proud of these; they were heavy, glossy stock with one of my paintings on one side and my contact information on the other – and handed it to her.
“You think yours are impressive? You should see mine. They’re to die for.”
“Hey, I have to go,” I said, “but my website with all my art’s on here. Let me know what you think!”
I left the coffeehouse and headed to the bar. I was still in a good mood – I’d met a cute girl, I was warmed up and ready to party like a rockstar with my buds – all in all a net positive from my perspective. I assumed that this was going to be the last I’d hear from her.
Analysis
At the time, I could have stuck around; there was definite attraction there, and we were having a fun time. The logistics of the situation – being in a coffeeshop with a big bag of art supplies – meant that I probably wouldn’t have been able to turn this into an instant date by hopping to one of the bars near by, but we could have spent more time hanging out at the coffeehouse.
As it was, leaving her with my card was a mistake; it often comes off as a passive-aggressive move and puts all of the pressure of making contact on her. I would’ve done better to say “Hey, I’m having a great time talking to you and I’d really like to see you again. Let me get your number and I’ll call you tomorrow,” and handed her my phone to have her punch her number in. That way, depending on how the night went, I would be able to send a ping text – “Hey, do you speak text?” or “This bar is lame, what are you up to?” - and keep the emotional momentum going. I’m a big believer in texting the same night I meet the person rather than waiting some arbitrary amount of time for fear of showing too much interest. Texting is a great way to keep flirting with someone, even bringing some sexual tension to the conversation; played right, it’s possible to turn getting a number into a make-out session that same night.
Still, I needn’t have worried…
Epilogue
A week later, as I was coming out of a movie, I had a voicemail waiting for me on my phone.
“Hey, this is April… you know, Reverse Cowgirl? I was wondering if you were doing anything this weekend…”
We ended up dating for four months.
- that would be the girl who I ran into seven times in one night who kept trying to steal my boots [↩]
- that would be someone I chased after for seven months [↩]
- her [↩]
- me [↩]
- Not her real name, duh. [↩]
- I hate that phrase, it sounds like jargon. Think of it like Glengarry Glen Ross: “ABC motherfucker. Always. Be. Closing.” [↩]
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Man, i wish i got cold approached like this. Id have been all over you. Lol.
This. This is what the nerdly ones need to see. Not the stupid PUA bull, but genuine, honest, conventional human interaction.
Also, highlight the fact that, even if the epilogue HADN'T been almost overwhelmingly cute, it helped set up a good night out on the town would make this a successful encounter, full stop.
Confidence, as always, is everything. The times seem a little brighter when you have a bit of swagger in your step.
Nice story doc. It's just that I think that I am not skilled enough right now to make a cold approach like this, complete with some sexual innuendo, without me coming off like a creep or something. Maybe when I start getting better at approaching, but currently the only time I can see myself making such comments is only after I met up with the girl at least once and that I feel like we both had a good time and are already playfully talking to each other.
Besides I just googled some of the innuendos here that I wasn't familiar with (I live outside the US, so some of these were brand new to me) – like "low hanging fruit" – that's a brilliant phrase LOL XD. I am officially adopting it to my own vocabulary from now on!
This is well done but I would put up an addendum; be really careful when using sexual innuendo in a cold approach with a strange woman. April obviously had that kind of humor or didn't mind it but starting off a conversation with a sex joke might offend someone else. I hate to say it, but I'm one of those prudes who would be kind of pissed if the first thing you ever said to me was a reference to a sexual act.
I'm probably not very cool.
Everyone has their limits, preferences, etc.
You're cool. You don't have to want to be approached or feel like you need to respond to a sexual joke if that's not your thing.
I agree with you, Devi. I would've been put off by a sexual joke right off the bat, and I would've been woefully disappointed that a fellow artist wasn't just interested in seeing my work. This is the kind of thing that makes me hate talking to strange men. Instead of having a nice conversation about a mutual interest, it immediately devolves into sexual innuendos that I then have to figure out how to respond to without seeming rude but while also not communicating that I'm down for casual sex.
Obviously, women are different, and this approach worked for April, but it would not have worked at all for me. Plus, there was no where in here where he found out if she had a boyfriend – this also seems to be a prevalent assumption in our culture that a woman who is anywhere by herself (without a ring on her finger) must be available. As someone who has had two extremely long-term relationships, I find this annoying. While I'd be happy to talk to a dude about my art if he was genuinely interested, having to choke out "I have a boyfriend!' after an immediate sexual joke is made is always awkward and leaves me feeling weirdly guilty (social conditioning, gotta love it!). Because if I don't immediately say I have a boyfriend, and I respond to the sexual joke with anything but horror, then I'm "leading the guy on."
Anyway, just wanted to let you know you are not alone in this, I'm a prude when it comes to talking to strangers, too!
"“Jerk,” she snorted and smacked me on the shoulder."
It was game on when she reacted this way. Seriously, once a girl flirtatiously calls you "jerk" or "asshole" and then smacks or hits you, it's as close as she'll ever get to shouting "please bang me" in public.
You could have easily converted this into a same-night lay.
Oh God. Pardon me while I run my head into a wall, repeatedly, because its more comfortable than listening to, 'OMG She TOUCHED me, that means SEX ON!!!' because secretly all women are whores longing to be banged by complete strangers. I applaud your tenuous grasp of respect for the female species.
You mistake me. It's not that "OMG! SHE TOUCHED HIM!!!" It's the specific way and context that she did. When a woman verbalizes that you're a cad, asshole, jerk, etc. but maintains a flirty, giggly attitude and goes out of her way to physically engage you while doing so, it's pretty much the clearest signal of sexual interest a woman will give in public, at least in my experience.
Knowing April as i do, i can say with certainty: No I couldn\’t have. Even if I stuck around, it wouldn\’t have been on the table.
And frankly I\’m pretty happy with how it ended up playing out.
I have literally done this exact move dozens of times, and would not have slept a single one of the guys I've done it with.
Maybe this is girl-speak for "hot damn, let's bang" for a few of the girls you know, but it's certainly not something you can apply universally to the female gender. In fact, you'll probably end up getting smacked or turned down flat if you try.
The lead-up was good stuff, but that conversation just sounded so lame. Like, cringe-worthy "why would I ever want to say this" kind of lame.
I don't mean this to sound as a negative, and I do want to be clear that I'm not arguing against it because I understand that it both works, people like it and the people who read this blog for advice can definitely better themselves with it. But even when I visualize my best self it, it doesn't come with that kind of material. It's kind of personally frustrating because pretty much every example I've seen of this kind of stuff (PUA, this place etc) comes out sounding like something I wouldn't want to say even if it 100% worked. Is there something I'm really missing here?
These aren’t like movie scripts or something….the thing to take away from these is the RESPONSE from the chatter, not the actual chatter itself. That, and the presentation. (I.E. You’re releaxed and enjoyable and just looking to have fun, as opposed to “Lemmie try out my amateur comedian act on you,” or worse, “I’m forcing this pre-scripted dialouge in hopes to get laid.”)
Hindsight is 20/20, and cold text reading it may sound “cringe worthy” to others, but hey. In the right time and the right place and the right mood and the right delivery, even the lamest of corny cornball can work.
You’d be surprised…
Context and presentation, and gauging their response. That’s all you need to take away from this.
I hope that's true, because it looks like cornball movie text when you read it.
The trouble with stories like this is, you can't put the chemistry between two people into words. You just have to assume it's there.
I'm telling ya…don't underestimate the power of the cornball =P
…..no, not THAT cornball. Gross.
Corny jokes. That's what I meant
What is said isn't the thing to focus on. It's the how and when. You should always be yourself (or who you're working to be), after all, so don't force anything. The point is that they were having a casual conversation that turned a flirtatious. It's more about keeping the flow of conversation going and being comfortable with it than it is about cringe-worthy dialogue – though, admittedly, flirting is often cringe-worthy, especially from the outside.
If your Best Self wouldn't say it, don't. But you gotta say something!
Great stuff as usual… BTW doctor, most of your advice does apply to middle class average young spanish people, as I've gratefully been able to concur over the past few months
I'm spreading the word among friends here in Madrid haha!
Anyway, upon reading your post I immediately thought: hey, this situation could turn out so well maybe just once out of 50 times. The exact mood you were in, the obvious thing in common you two had, the handpainted hat, her forgiving and even going along with your risky jokes… As in "aaaw, come on, no matter how inspired I am doing a cold approach, this could never happen to me, some Hollywood scriptwriter came up with it… The girl in the picture even has a resemblance with Cameron Diaz!" But then again, and like you've said so many times, it's all about trial and error, not being afraid of rejection and just getting on with it! Meaning if it only can turn out so well once out of 50 times, man the f***k up and fail 49 times if necessary!
Not to ruin the illusion, but that picture isn't April. That's a stock photo used to illustrate the article.
These videos changed my outlook on approach. Everybody here should check them out.
<iframe width="640" height="360" src="http://www.youtube.com/embed/S-WvvFQ_x9M" frameborder="0" allowfullscreen></iframe>
<iframe width="640" height="360" src="http://www.youtube.com/embed/tw1zGQ6St1M" frameborder="0" allowfullscreen></iframe>
Cant embed…
Direct links http://youtu.be/S-WvvFQ_x9M http://youtu.be/tw1zGQ6St1M
From the girl in question: I appreciate the good Doctor's entertaining and (mostly) accurate write up of how we met and, as I'm clearly a girl that enjoy's dating nerds, I thought I'd share just a few quick insights about why this worked from my perspective:
1. Doc mentions this already but it bears repeating – mentioning that he had somewhere else to be and giving me the polite option to exit the conversation had the biggest impact on the pick up being a success. Unbeknownst to him, beneath the aforementioned cowboy hat and shield of flirty confidence was a neurotic mess of social anxiety. In previous situations when guys had hit on me, I'd make up fake boyfriends or rude reasons to exit the conversation even when I was interested – often especially when I was interested – because I'd get nervous. Remember boys (and girls) meeting people can be nerve wracking for all parties!
2. He read his audience. This was key. To the those of you who said that our exchange was either lame, corny or too overtly sexual – you're totally right! Reading the recap even had *me* cringing a bit… but we also met over 5 years ago. We were both different people then at earlier stages of our social development. Would we both be more nuanced, smooth, and witty if we met today? I think so (although Mrs. Dr. Nerdlove might have something to say about that…) It worked though because he read the cues I gave and responded in kind. Also when I (playfully) indicated he was approaching a line, he backed off. This let me know that he was someone that would let me set the boundaries of what I was comfortable with.
3. Finally, we genuinely had shared interests that we talked about. That's the entire reason I called him up – even if he was just killing time by talking to me, even if he wasn't actually as interested as he had seemed, I knew I could always play it off. "What, no I wasn't calling to see about a date, i just honestly wanted to get your opinion on the best way to approach 2-point perspective in the third panel of a comic…." The shared interest is what got me to call him, why we enjoyed dating for four months, and the basis of a friendship that's far outlasted the romantic relationship.
Finally to the commenter that thinks that because I was flirty and made physical contact, I would have been an easy same-night pick up: Nope, wasn't going to happen. That was one of the best things about dating the doc, even in the midst of his pick up artist past he totally got that there was a difference between "this girl seems like she wants to sleep with me" and "therefore she owes me the sex!" More importantly though, whether or not I would have been an "easy" pick up that night (or any other night with any other guy that's picked me up) that's always depended entirely on how I'm feeling about myself and what I happen to be looking for in a situation – not at all on what the guy does. I've resisted the temptation to immediately sleep with some really wonderful guys, given into the urge to go home with some true jerks, and every combination in between. If this situation happens to you- be happy that she's flirting back! Let sex not be the make-or-break barometer of success.
I believe point 3 is the biggest point. The moment you can step outside of the "I'm approaching a woman omg" game and into "I'm approaching a really cool person" instead, especially if it's over a shared interest, you're going to come out way ahead on confidence and comfort level in the conversation to begin with. If you then remember points like #1 and 2 as well, more out of respect for this cool person you're meeting instead of 'steps to have her like me' then you're well off there, too.
Even if it winds up being a person you don't like, or they wind up not liking you, giving them the 'easy out' (like #1 in April's post) and reading their comfort level accurately (#2) is basically treating them with respect. Get used to doing those kinds of things for everyone you meet and not just people you want to 'pick up' and you'll make more friends and probably even relationships too.
This was an all-round good example Doc, nice one.
I'm absolutely the same way about the whole making up exit strategies even if I really like the guy! Not so much anymore, but still, meeting people can be nerve-wracking. Sometimes all you're looking for is a way to halt the conversation so you can calm yourself down and get comfortable, but the first thing that pops into your head is what you used to turn down the last creeper like the fake boyfriend.
And thank you for addressing the whole a touch doesn't lead to sex issue. I can't tell you how many guys think that calling them some form of a jerk with a slap, no matter how playful or full on meaningful, means "take me now." Ri-damn-diculous.
Man, there's nuances and stuff that I just have no idea about when it comes to talking to a girl. There's a ton here I'd never even think about or consider.
Coming from a guy with my level of experience, I pretty much read through the whole thing thinking you were a pick-up artist/genius, with the magical abilities to talk to any girl you wanted. The commentors have really tried to take the wind out of your sails.
Either way, you make the whole process look so very easy. I'm slightly jealous of you now, but that's natural.
Moral: sexual relationships are difficult for everyone except for Hugh Hefner and Doctor Nerd Love. Or anyone with confidence/attractiveness/whatever the hell girls like.