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.
So with that in mind, I give you the tale of the Reverse Cowgirl.
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.
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.
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.
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.
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.
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.
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.
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?”
“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.
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…”
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.
“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.
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…
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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