There’s an important rule when it comes to self-improvement, especially when it comes to dating: some things can only be learned from experience. It’s easy to get caught up in dogmatic rules, but time and experience can teach you when exceptions arise. For example: I’m a big believer in the efficient use of one’s time and energy in dating. If someone rejects you, the best thing you can do is just shrug your shoulders and move on. But sometimes, a little persistence can mean the difference between getting the brush-off and getting the date… or more.

Being able to recognize those moments – and how to take advantage of them – however, can be tricky. Sometimes you need an experienced hand to point them out. Which is why it’s time to put my dating life back on the table with another Anatomy Lesson.

I cover a lot of topics, ranging from how to avoid being creepy by accident, what it takes to strike up a conversation with complete strangers and why playing the long game can give you better odds than hoping for instant, immediate attraction. But sometimes it can be hard to see how these all fit together. This is why one of the things I like to do here at Paging Dr. NerdLove is break down real-life examples of dating and mating to explain what went wrong, what went right and what we can learn from them.

As always: names and certain details have been changed to protect the innocent and guilty alike.

Now before we get started: this example happened while I was still pretty deep in the pick-up scene. There’re some aspects to how this went down that I’m not not proud of – not the least of which being that I was trying to get someone to cheat on her boyfriend. That was pretty scummy of me at the time. With that having been said, there is a lot to learn from this and the boyfriend issue was a part of it. So stick with me and all will be made clear.

With that being said: let’s talk a little about the saga of Lady Jay and why a little smart persistence can go a long way.

The Setup

Back in my PUA days, I’d been developing a pattern for my nights out downtown. My friends and I would meet up at one bar for what we’d call our “warm ups” – low-investment approaches early in the night to get us into a more social mood before heading out for more looking for more “serious” prospects.

As a general rule, the nightlife in Austin would start around 10 PM and slowly build until reaching a crescendo around 1 AM. Since most people you’d meet early in the evening would only just be starting out, you wanted to conserve your energy. Certain bars were for early in the evening when things were more chill and we were only trying for numbers. Other bars were for later in the evening, when the higher energy and later hours meant that they would likely be more interested in hooking up that night. The general assumption was that you might want to circle back around to someone you met earlier, but the majority of your focus should be on the women you meet later on.

Of course, all that went out the window when I ran into one of the hottest women I’d ever met at our warm-up spot.

Analysis

Warm-ups are actually an important part of meeting people. Just as you don’t want to start running a 5k cold, you don’t want to start a social night out in a solitary headspace. It can be hard to shift into that social mode and leave you feeling anxious and out of place. This is one of the reasons why it’s good to go out with friends whenever possible; meeting up with them beforehand helps you get into a more talkative and outgoing mood.

Even if you’re going to be rolling solo or meeting up with your friends later, you can still warm up beforehand. Talking to friends on the phone (actually talking, not just texting) is a great way to stretch those social muscles before a party. Failing that, starting low-investment conversations with people around you – talking briefly with the waitress at dinner, for example – can help you warm up and get ready to meet people.

Also important: developing a feel for the energy levels of the people around you. Parties and social gatherings tend to follow a waveform pattern. The earlier you are, the more stand-offish and low energy people tend to be; they’re usually less likely to be receptive to more than basic conversation. People tend to loosen up and get more excited and energetic as the night goes on, peaking an hour or two before things close down for the night.

The Approach

She had come in with a few friends who had headed straight to the bar, leaving her standing over by a table, checking her phone.  Lady Jay was stunning to say the least. A little older than me¹ but dressed to impress with a blue sparkly number that showed off an ass like damn and breasts like phwoar.

There was no way I was not talking to her, warm up or not. I had a couple drinks in me at that point and was feeling cocky, so I decided to go with a slightly more aggressive² approach than normal because… well, to be perfectly honest, I thought I didn’t have a chance so fuck it.

“So is he in a lot of trouble?” I asked, nodding at her phone.
“Who?” she replied.
“The guy you’re texting who’s clearly late.”
She smirked at me. “Who says I’m texting a guy?”
I blinked. “Well if you’re texting a girlfriend, I’m going to be walking away from this very disappointed…” I replied. Mentally, I kicked myself. It was not my smoothest moment.

She dropped the phone back into her purse. “Be honest. You didn’t come over here just to ask me who I was texting,” she said, giving me a challenging stare.

At this point in my development, I’d met very few women who were willing to sass me back right off the opener; most of the women I met in bars either would reject me right off or tended to be much more indirect. This was the first time I’d run into someone who was willing to straight-up call me out on what I was doing.

It was simultaneously the hottest and most intimidating thing she could’ve done and it completely threw me off my game.

PUA protocol at this point would be to shoot back with something snarky in order to take back control of the conversation. I, on the other hand, was so surprised that blurted out “OK, fine. I thought you were smoking hot and I really wanted to meet you.”

She laughed. “See, now you’re actually interesting,” she said, holding out her hand as though she were expecting me to kiss it. “I’m Jay.”

“And I’m thinking you should have a drink with me,” I said – desperately trying to regain my mental footing. This, in fact, would define most of our conversation that night – her managing to keep me off-balance by continually giving me unexpected levels of playful shit, followed by surprisingly deep conversation, punctuated by more teasing. I liked someone who could banter with me, but I hadn’t met anyone who managed to upend my expectations. She refused my offer of a drink but did sit with me instead. If it wasn’t for the fact that she kept touching me – a brush on the arm, a nudge with her foot –  and playing with her hair as we talked, I would’ve been convinced that she didn’t like me much. Eventually I managed to start zinging back, which made her laugh and lean in. It seemed like a natural moment for a kiss, so I moved in… and got the push-back via a finger on the lips.

“I don’t think my boyfriend would approve,” she said with a grin.
“…you waited until now to tell me you had a boyfriend?” I replied; if I knew I wasn’t going to have a chance with her, I wouldn’t have spent so much time flirting.
“What can I say? I was having too much fun talking to you. You’re interesting.”

As she stood up to leave, she turned and looked at me over her shoulder. “Maybe I’ll see you around some time.”

I had never been so confused in my life. And I was absolutely determined to have her.

Analysis

I probably learned more about flirting from Lady Jay than I did from almost anyone. She was the epitome of the push-pull dynamic – drawing in with a compliment then taking it back with a tease. It made her difficult to read and maddeningly hot. It wasn’t until I could match the same rhythm that she warmed up to me, and even then it was clear that I was playing catch up. Keeping someone slightly uncertain can actually increase their appeal – sexual tension, after all, is thwarted desire – but needs to be done carefully. Past a certain point, you’re no longer flirting so much as playing head games, which nobody likes.

The Second Encounter

It was sheer coincidence that I ran into Jay a second time. This time we ended up meeting at a club across the street from the warm-up bar; it was a favorite of ours because we’d gotten to know the bouncers and were able to skip the line. I made my traditional beeline to the bar when I felt a tap on my shoulder.

“Hey, Mister Pick-Up Line,” she said with a grin.
I gave her a mock-stern look. “Hey Trouble,” I replied. She pouted at me.
“How’m I trouble when I’m so nice?”
“Because you’re the one who’s going to get me in trouble if you keep looking at me like that.”

She laughed and punched me in the shoulder. I offered to buy her a drink, but she shook her head. “I’ve got my own,” she said. When I arched an eyebrow at her, she reached into her purse an wiggled a flask at me. “I like keeping track of how much I’ve had. Plus, they never have what I like here.”

“What do you have in there?” I asked, my curiosity piqued.
“Tequila” she said winking. I snorted. “What, you don’t like tequila?” she said, almost affronted.
“Oh no, I used to love tequila shots. Then, y’know, I learned I could get good alcohol.”
“That’s because you’ve never had the good stuff,” she said with a sniff. She hooked my arm with hers. “Come with me,” she said, pulling me over into a corner. “If they catch us, we’re going to get kicked out of here.”

We huddled up near the booths as she passed me the flask. “Don’t shoot this. Sip it.”
It was my first time with straight tequila… and it was damn good. We stayed there for a good 15 minutes, passing the flask back and forth like teenagers at prom. I put my arm around her waist and she leaned in with me… but again, gave me the finger to the lips when I moved to kiss her. “Boyfriend, remember?”
“I don’t see him anywhere, do you?” I said. She shook her head.
“Doesn’t matter. Still exists.”
“You’re the one who pulled me into the corner,” I responded. She grinned.
“I didn’t say I didn’t like you. I said I had a boyfriend.”

That night we exchanged numbers; I joked that as long as she was going to be stalking me, I should be able to tell her where I was to make it easier on her. Later that night, I sent her a text: “Hey Trouble. Just so you know, I’m going to keep hitting on you.”
Five seconds later, she wrote back: “Well you’re certainly welcome to try.”

Analysis

This is where things started to get interesting. On the one hand, she was dating someone and wasn’t interested in cheating on him. On the other hand, she also was making it clear that she liked me… and was dropping considerable hints that hooking up wasn’t entirely out of the realm of possibility. Again, the push-pull aspect of our interaction was keeping me interested.

A lot of people would say that she was just trying to keep me on the line because she liked the attention, which is entirely possible. And to be honest, that isn’t necessarily a bad thing as long as everybody is on board. However, her behavior – approaching me instead of waiting to be approached, giving me her number – speaks far more to genuine interest than manipulation. Similarly, the moments of intimacy – pulling me into the corner, standing in close and sharing the flask – implied a deeper interest than just appreciating being hit on by a younger guy.

Most importantly, however, was that I’d been given explicit permission to keep flirting with her. This is the point where persistence comes in to play; she likes flirting with me, which only gives me more opportunities to win her over. At this point in my development, I had been quite successful, so I was confident that time was decidedly on my side. The key is to be careful not to cross the line. That’s the hidden meaning behind “welcome to try.” If I played things wrong – by being too persistent, getting needy, entitled or pushing things to the point that they weren’t fun any more, then I was going to get cut off.

Finding The Equilibrium

I spent the next several months (yes, months) walking a line with Lady Jay. On the one hand, all signs pointed to the fact that she liked me. On the other hand: boyfriend. I wasn’t so concerned about the boyfriend – as far as I was concerned, he was a temporary roadblock to what I wanted. The key – or so I thought – was going to be getting Jay’s attraction level high enough that it would override the existence of the boyfriend. At the same time: well, I wasn’t going to stick around waiting for her. Not when there were other women to hook up with. So it was a matter of keeping contact open and maximizing my time with her, but not giving signs that I was getting needy.

I knew from experience that more sexual flirting made actual sex more likely – but I couldn’t just come out and say “I want to fuck you”. There needed to be a more playful aspect to it – something fun to draw her in but also not tip my hand. She knew I wanted to bang her. I knew I wanted to bang her. But our entire relationship was based on the banter and dance of sexual frustration. The answer: texting. Texting made for perfect flirting territory. It was a way of keeping lines of communication open without being too pushy, and people tend to be more willing to be sexual via text than they would be over the phone or in person. So I would occasionally send bait texts: “Hey, I had the craziest dream about you last night. So I just wanted to say ‘hey’ and also ‘stay out of my dreams’. You make it hard to concentrate.” She’d send back “Aww, but I like you dreaming about me.” Another time I sent “Hey, just saw your evil twin.”

She wrote back “No, you saw the good one.”
“What makes you so sure?”
“Because everyone knows bad girls are hotter.”

If I was out and about downtown, I’d make a point of texting her to see if she was around and wanted to meet up. If she was downtown already, she’d usually meet up with me – at least for a little while. We’d banter, we’d flirt, I’d pull her in close… but that was as far as it ever got. It seemed like a battle of inches; she was fine with my putting my arm around her. She was cool leaning in against me in intimate space… but never anything further. It was maddening in its own way; I could tell she was in to me… but I could never quite get it over the last hump (as it were).

On the plus side, however, I was developing an appreciation for fine tequila.

Of course, I inevitably screwed myself.

There were plenty of times when we’d run into each other at various bars or clubs by legitimate coincidence.

We’d talk and flirt, but then I’d move on and flirt with other people. There were a few memorable occasions where other girls I’d been seeing would come by and I’d end up making out with them in front of Jay.

And then I pushed things too far. On one occasion, I ran into Lady Jay at a club with her friends. As I came up to say hi, she waved me off. Confused, I went back to my friends. A bit later, she came up. “Sorry, that’s my boyfriend over there,” she said, gesturing at a guy by the bar.

I was aghast. This was my competition? He looked like the lead singer of White Lion after a lengthy prison stay. I couldn’t believe that I was being functionally cockblocked by someone who looked like he was in a Jackyl-with-a-Y cover band… and said so. “So… does he ever tell you about the days he opened for Winger?” I asked, getting a chilly smile in return. “No, seriously. Can you ask him to come over here and do ‘When the Children Cry?'” From that point on, when I ran into Lady Jay, I’d make a joke about her boyfriend.

That was a mistake.

“So… did he win you over with his rendition of ‘More Than Words’?”³ I asked once. And that turned out to be once to many.

“You know what? I’ve got to go,” she said. She turned and walked off without another word, leaving me with my metaphorical dick in my hand and the vague feeling that I’d just irreparably fucked myself.

Analysis

First and foremost: my persistence was not only welcome but working. Jay was very responsive; even if she had no intentions of dumping her boyfriend, she was enjoying my presence in her life. It’s a situation that requires being socially well-calibrated and aware of how other people are behaving; it’s easy to go from “welcome persistence” to “annoying nuisance” to “dear god why is this person not getting the fucking HINT!”  If I’d started getting pushback or detecting signs of The Fade⁴ I’d have bailed.

Next: this was a master class in how to do things right and wrong… occasionally at the same time. On the one hand, flirting with Jay via text was good. Not only did it help keep her aware of me, but it was easier to escalate sexually than it would have been in person. Text, to many people, just isn’t as “real” as talking on the phone and they’re more willing to go further. It also helped keep a barometer on how she felt about me. I spent more time initiating the texting, but she almost always responded quickly and enthusiastically, rather than with increasingly short replies.

On the other hand, insulting her boyfriend was a stupid, stupid move. To start with: it was just plain mean. Our flirting was fun as long as it was light and fluffy; the occasional mention of the vague obstacle entitled “boyfriend” was a part of the game. Talking about her boyfriend the person made it personal and dickish. Plus: not only did it make me look petty and immature – not exactly appealing traits in a man – but it also insulted Jay. After all, by mocking her boyfriend, I was mocking her taste in men. What does it say about what I think of her if I think her boyfriend is such a jackass? There’s a lot in PUA circles about “boyfriend destroyers” – mythical scripts or patterns that can diminish a boyfriend in his girlfriend’s eyes and make you that much more appealing. They’re bullshit. Bringing her boyfriend into it only made things worse.

Chasing other women, especially in front of her, didn’t help. It certainly didn’t necessarily hurt, but the biggest benefit was that I was still seeing other people instead of just pining after Jay. It didn’t magically make her jealous or somehow make her want me more. At best, she knew I wasn’t obsessing about her. At worst… well, it was basically neutral.

The Close

I was fairly convinced that I’d completely blown things with Lady Jay after the last incident. I tried apologizing – sincerely, even – but got nothing back. In fact, she didn’t respond to my texts for weeks afterwards. I hadn’t seen her downtown, either. It seemed that I’d pushed my luck too far and it had finally run out. I was surprisingly saddened by this; yeah, I wanted to sleep with her, not date her, but I’d really enjoyed our bantering and duel of wits. I was finding that I missed the back-and-forth teasing about who was trying to get into whose pants. Trying to get her in bed had been the project of six months at this point and it seemed almost a shame that it ended this way.

One night about a month later, several of my friends and I were planning a party at a local club – getting bottle service, reserving a significant portion of the club, the works. On a whim, I texted Jay, telling her I’d be there and she should totally stop by if she was going to be around. As far as I was concerned, it was tossing an invite out into the void. So I was surprised when Jay and a friend came by and made a beeline straight for me. Evidently they’d been out for a while already and after getting my message, Jay had decided… what the hell.

It was the first time that she’d been around my buddies for any length of time. They’d heard the stories and seen me flirting with her, but it was the first time she actually talked with any of them. I headed to the bar for tequila shots, handed one to Jay and said “Come with me, we’re dancing.” This was going to be my last-ditch effort to move things along; a little bump and grind on the dance floor to get excited and then… well, who knows? And it looked like it was going to work; as soon as we hit the dance floor, Jay was all over me like a cheap suit. We weren’t making out, but I was damn near getting humped straight into the ground as she was sliding my hands all sorts of interesting places. After what seemed to be too long and not nearly long enough at the same time, Jay mentioned that she had to go. I thought I was in like Flynn and offered to walk her to her car – conveniently parked in the garage across the street.

Standing by the car door, time began to slow down. We were both out of breath, yet breathing in synch. I put my hands on her waist and pulled her close. As she melted into me, our faces came closer and closer together, ever so slowly as the tension began to build…

And I got a finger to the lips. “Not yet,” she whispered. “I still have a boyfriend.”

Analysis

The magic words there? “Not yet.” Not, “no”. This wasn’t a refusal, this was a “need more time” – although I didn’t realize it at the time. More than anything else, persistence requires patience.

The smartest move I made was simply apologizing. Jay took her time in forgiving me, but the fact that I recognized the mistake and made a sincere apology for being an asshat earned a lot of good will back. If I hadn’t, she wouldn’t have spoken to me again afterwards.

The party also ended up working to my benefit. Having my friends talk me up to her helped solidify me as a cool guy – although this would’ve been more valuable earlier on. The biggest benefit, however, was the dancing. Humans are bad at recognizing how we feel; we feel the symptoms and ascribe causes to them later. It’s known as misattribution of arousal, and when done right, it works to your advantage. Anything that gets the heart-rate up increases sexual arousal because we tend to associate the feeling with a person rather than an event. The dancing got her hot and bothered – especially after seven months of flirting and building tension. All that we lacked at this point was for Jay to give herself permission – as it were – for the release.

The Payoff

A week later, I got a text. “I don’t have a boyfriend any more. So where’re you taking me tomorrow night?”

Later – much later – as we were cooling off in the afterglow and feeling the air tracing patterns over our skin, I turned to her and said “So… what made you decide that you were going to sleep with me?”
She yawned and stretched, sat up and began to collect her clothes.

“You didn’t give up. I liked that.”

 

 

1. As I would later find out, she was a good ten years older, in fact. Decidedly not a bad thing… [↩]
2. also: douchebaggy [↩]
3. Fun fact, my brother used to be very popular in middle-school because he could play ‘More Than Words’ on guitar… [↩]
4. when someone starts to become non-responsive in hopes that you’ll go away, rather than having to actually have an awkward confrontation [↩]