I’ve wagged my tongue for many years about the importance of knowing logistics when meeting women. Big Four and all that. And for good reason: it’s the difference between driving sober and driving blindfolded, high on mushrooms.

But there’s a caveat to this: you’re better off taking those mushrooms if the girl’s not interested in you, because logistics won’t matter then. And conversely, if she does like you, she can help you navigate even the rockiest terrain.

When my Philadelphia buddy SW told me about how he ended up with his girlfriend, even though she was knee deep in med school and had even told him she was too busy to see him, I thought it would provide a helpful example of this. And it’s just a cute story. So here you go:

I should start by saying the adage, “you always find what you’re looking for when you’re not looking for it.” It rings so true here.

When I went to the biergarten back in May, it was not to seek out girls. I was coming out of my first week at a new apartment and exhausted after the big move. I was also preparing to go on a two-week trip abroad to Spain.

I did enjoy the biergarten, though; it was a nice departure from moving. I went there with my friend B because one of his friends was celebrating graduation. He and I went for a walk around, which ended up lasting 30 seconds because this girl at a table caught my attention immediately, with her animated storytelling and her … dress she had on. So I sat down next to her and introduced myself, and B followed suit and sat across from me to talk to her friends.

dating a woman in med schoolD, as we’ll call her, was with 10 med student friends, celebrating the completion of their second year of med school. Little did I know, thanks to the liter pitchers they serve, that D told me (half jokingly, half serious) not to contact her for six weeks because she was to begin studying for her Boards, and the exam was six weeks away. Maybe then we could try something. But of course, I “inebriatedly ignored” that fact and called her two days later.

With a little luck, she answered and we set up a date for the following Friday when she had a little free time. I had to be a little persistent as she said she had to study couldn’t be out late. We had our first date that Friday, and we hit it off the moment we reacquainted ourselves.

The Jerry McGuire quote of “You had me at hello” rang true here for me, because she was more beautiful standing in front of me than I could have ever imagined before at the biergarten. We sat down at the bar for a beer at a nice little place she suggested, and were laughing and leaning in towards each other.

Within the first hour, I decided to say what I never say in the middle of the date unless it’s positively going perfectly: “I am having a wonderful time and really want to kiss you right now.” Her answer laid the groundwork for our relationship: “I’ve been waiting 25 minutes for you to say that.”

We went on to continue the date for another two hours. I even invited her back to my place to have a final beer and show her the place I so proudly just moved into. After we parted I said a little coyly, “Weren’t you supposed to be not out late?” And she said, “Yeah well, I said that before I decided I liked you. That was my out in case things didn’t go well … sorry!” She laughed and I actually laughed too.

And ever since, she’s been ready for everything I’ve set the pace to do. The next few dates, we had each other over for dinner so we could show how much we enjoyed cooking. The physical attraction and intellectual attraction were very high in our case, mutually. It was hard to not go too fast, but I was better at it now than I used to be and knew that this was the only way it was going anywhere.

I knew she was interested too, because her med school friends were saying, “WHAT, you two met and BEGAN dating? … during boards?” They all said it like it was the most unheard-of thing. But each time, we’d just look at each other and laugh and shrug.

That all made me feel pretty good about myself, and it showed me how much I meant to her as well. It wasn’t difficult for me to win her affection, thanks to our chemistry from the beginning. And in all honesty, she could be doing or wearing the most mundane thing and I’d be turned on by her. It’s all about chemistry. If it’s not there, it’s not there. I’ve tried to create it in the past, and you just can’t.

Anyway, the boards were present throughout our early dating. We’d text usually once every day (or two) in the beginning and it would increase with time as we got more interested in each other. But the logistics became more and more challenging as time went on. If you’ve never read this, there’s a guide for people like me on “How To Date A Med Student” and it is dead-on accurate. She actually was the one to show it to me, as a joking “I warned you” precursor to future dating. But as I always tell her, in the words of Barney Stinson, “challenge accepted.”

I would consciously think about being in her shoes, and when the best times to contact her would be, when we would be better able to meet up (later in the evening always worked better, since she had long hours of studying, and I learned this through time and just asking). I’m a pretty laid-back and go-with-the-flow kind of guy, and that’s how you have to be to date someone in med school. I think they should put that in their guide.

Being understanding of a busy significant other can go a long way. She will appreciate that about you to no end. I even helped her study a little bit. It baffled me how there was this girl who was the busiest girl I’d ever met, and here she was going out of her way to find and make time for me, in a way that was more genuine than any other girl had before. That was a real thing for me, and I reciprocated that feeling every chance I could. And it was ultimately what led us to become official.

Was this a tricky navigation of two different paths in life trying to become parallel? Sure. But what I’ve found after dating as many women as I have over the past few years, is that it’s not the easy ones that tend to stick around. It’s the challenging ones. Because they’re smart enough to see what they really have in front of them, and want to work at it as much as they see you doing the same.

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This is the second and final installment of my tag-team effort with Tall Anna about the importance of men’s height to women. Click here for Part 1.

GK: You do know your science, Anna, and I can’t argue with any of that. I know you don’t follow basketball, but sometimes I see height’s emotion-over-logic effect on NBA general managers.

Because 7-foot centers dominated the league for so long, a lot of GMs seem to keep drafting busts like Hasheem Thabeet and Darko Milicic over better, shorter players because it feels right to have a star big man. Even though shorter players have led teams to championships.

For reasons you gave, a taller guy does own the advantage, and at least you gave those shorter guys a chance; other women don’t. However, there is a way to crack this code in some cases — and it exists exactly because it’s so hard for women to explain their attraction to height.

Height is a means to an end: it makes a woman feel protected and safe. This feeling is paramount to women and there is no single trigger for it — I’ve been stunned when my past girlfriends told me they felt safe around me, considering that at 5-10, 147 pounds, I could barely fight off a chihuahua.

A taller guy enjoys the express subway line to Protection Land. A shorter guy must take the commuter train: it’s longer and trickier, but he can still get there by creating that first-impression feeling that you mentioned.

If a shorter can guy express other “alpha” qualities — dominant eye contact, a confident posture, having a compelling life, keeping a woman challenged, touching her and holding her like it’s his birthright — he can still make a woman feel safe.

I think of my good friend Tre Tre, who has been with plenty of taller women, including one girlfriend who was a full 2 inches taller. And a former student of mine who stands 5-4 but is in outstanding shape and has made a habit of dating personal trainers.

ok cupid messages height

Also, you mention that tall women get overlooked more, which is true. There’s an OK Cupid chart (see above) that shows a precipitous dropoff in interest above 5-foot-9. When women have fewer options, they tend to be less picky, which can work to a man’s advantage. A shorter guy may indeed have a better chance with a tall woman than with a 5-foot-5 one, simply because the former gets hit on far less.

My hypothesis is this: a guy under 5-9 has better odds attracting women offline than online, because he can better subvert a woman’s height biases by demonstrating his attractive qualities in person. Unlike with dating sites, a woman at the coffee shop can’t instantly click on 10 other guys.

Your thoughts?

ANNA: I think your hypothesis is spot-on, GK. Online, that taller woman is probably much less likely to give that shorter a guy a chance simply because she can filter him out and focus on the ones within her ideal height range, which, let’s face it, is probably anyone taller than herself.

In person, though, that same guy could immediately show her that a) the height difference isn’t as big of a deal as she may think it is, and b) his awesomeness makes up for what he may lack in height. Plus, if you’re sitting at a cafe or at a bar, height isn’t even an initial factor. You can start up conversation without even knowing how tall the other person is.

But I do want to add this: dating a taller guy isn’t just about wanting to feel protected and safe. I’m a confident 6-1, and in heels, up to 6-5. I realize I’m female, and that automatically puts me at some sort of disadvantage walking home alone at night. But 99% of the time, I feel pretty darn sure that, should I need to, I could kick some ass on my own—or on my date’s—behalf. Being really tall, confident, and aware inherently keeps me rather safe.

Sure, when I’m with B., that safe feeling doubles. But it also doubles when I’m with another person, regardless of their height. Bottom line: I don’t need a tall guy to make me feel safe in this crazy world.

All that said, making a gal feel protected is to your advantage, because who doesn’t like to feel taken care of just a little? (Just don’t take away her independent-woman feeling in the process.) And like you mentioned, GK, by showing her your “alpha” qualities, you’ll not only make her feel safe, but also pretty into you.

The key, however, is to work your magic in person—not for weeks over email or OKCupid messages.

GK: You’ve touched on one of the biggest ways my game has improved over the last five years: I’m way better at guessing a woman’s body shape when she’s sitting at a bar or cafe table. I’m a regular Sherlock Holmes at gathering the evidence, and I won’t give the whole secret away, but I will say this: the ankles usually don’t lie.

Thanks for clarifying my point on feeling protected — I have no doubt you can kick some serious behind if need be. By “safe,” I don’t think it’s always a literal protection from danger that women seek. But even as gender roles change, women are conditioned to want a man who’s dominant to them (one recent, regrettable example being “50 Shades of Grey”), and height is the most literal manifestation of that. So, height often wins out — especially online.

(I should add that if we go rock-climbing as we’ve discussed, I will absolutely feel safer with B. around.)

Still, perhaps the greatest reward of my coaching days was seeing conventional wisdom shattered. The underdog rarely wins in nature and the bigger or manlier guy usually gets the girl. But it’s inspiring to have witnessed guys of many sizes, personalities and backgrounds succeed by finding their manlier side — not with a laptop, but with some good old-fashioned brass balls. It’s sort of like wearing lifts, but way cooler.

You know what, Tall Anna? It just inherently feels better having you on my blog. Will you promise to join us again?

ANNA: Absolutely, Greg. But now you really have me curious about these secret conversations you’ve been having with women’s ankles. Perhaps we can save that for another time, though.

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You would be surprised how hard it can be to find a 6-foot-1 woman. I’ve been trying to get my friend Tall Anna back on my blog ever since we teamed up to talk about statements vs. questions over a year ago.

tall womenAnna was playing hard to get by spending her time on such things as writing fashion copy, traveling the world and falling in love with her boyfriend. But if I can wait all year for “The Hobbit” to appear in theaters, I was going to keep persisting.

It took the perfect subject to finally track her down. We’re going to talk about how important a man’s height is to a woman, and Tall Anna is uniquely qualified for this.

Let’s first state the obvious, Tall Anna. I’m pretty sure we’ll agree that all things being equal, women DO prefer a guy who’s a little bit taller and is a baller. The question is, how much more important is it? And how much of a chance does a guy have with a girl who’s taller than him, or who is merely an inch or two shorter than him?

ANNA: It feels great to be back, GK.

And while I don’t really want to put words in the mouths of women I don’t know, I suppose I’m going to anyway for the sake of our discussion. Bottom line, I’d say yes. Short and tall women alike typically (but not always) end up with a taller partner (and I’d go out on a limb and say they prefer one, too).

I recall a few friends giving me grief when I’d set my OKCupid search filters to only show me men over 6-feet tall. After dating my fair share of men who were significantly shorter (5’8″!) than me to just my height, I knew deep down that my life partner would be taller. It just inherently feels better.

But the answer to your height question is not as clear cut of a formula as, say, age difference. A guy can’t just cut his height in half then add 7 inches. (And I’d say height is much less important than age, too. Age, to an extent, carries with it implications about maturity and where you are in life that height just can’t touch.)

The determining variable in the height equation? Confidence. Both the lady’s and the gentleman’s.

GK: Anna, it’s a good thing we men can’t cut our height in half to add seven inches. Because you’d have a lot of hung dwarves out there.

There’s one word you used that caught my eye even more than confidence: feels. That’s the invisible Olympic hurdle a shorter guy faces with women.

You don’t need to put words in women’s mouths — I’ll do it for you! As far as online dating goes, and that is how you found your boyfriend, there’s plenty of evidence to show that women like ’em tall. One online-dating study even found that for a 5-foot-9 guy to be as attractive as a 5-10 guy, he needed to earn $30,000 more. That’s A LOT of extra time I’d have to spend at the lemonade stand.

I want to talk more about online dating later, since a lot of our discussion hinges on where a shorter guy is meeting women. But let’s get back to feeling right around a taller guy. I’ve met your boyfriend, and he is indeed tall. He also seems like a genuinely cool, confident guy who you share common interests with, and he does indeed have a few years on you, so you’re not whistling Dixie about age.

Still, just what does his height make you feel that the other guys didn’t? And could a confident, 5-9 version of him have made you feel the same way?

ANNA: That feeling I mentioned is so hard to pin down because I think it’s simply written into my genetic code. It’s just how I’m wired, and frankly, how women, in general, are wired.

When two people date, they are consciously gathering data points about whether or not they want to spend more time with each other, right? But before the first date comes the first impression, those few seconds in which we’ve subconsciously asked ourselves: might I want to make babies with this person? It’s our biological drive to seek out the genetically healthy and fertile (even if you’re not looking to start a family RIGHT THIS VERY MOMENT), and it’s hard to fight instinct and win.

In western society, the taller the guy, the higher his reproductive success. (Tall up to a certain point, anyway.) Height is right up there with pheromones, facial symmetry, even voice pitch and the way someone walks—the parts of sexual chemistry that act behind the scenes to significantly influence whom we find attractive.

So I guess, to a certain extent, my body knew before my mind did that it wouldn’t work out when I dated those under-6-footers. And being with my partner now—let’s call him B.—who’s 6-5, we physically fit together. When we walk side by side, my hand is at just the right height to be holding his, and my arm is at just the right height to wrap it around his waist. When we cuddle, no matter which way you contort it, I fit just right in his nook. When I want to wear my tallest pair of heels, he’s still just a hint taller. A 5-foot-9 guy just couldn’t give me that sense of rightness and feeling of belonging together.

And hey—being a tall woman isn’t as glamorous as supermodels have made it seem. I’m working against my own biological disadvantage: shorter women have higher reproductive success, and all those tall guys biologically prefer them, not me.

I don’t want to sound all doom and gloom, though. There are always exceptions, and I know some of them, including my sister, who’s happily married to her ever-so-slightly shorter husband.

Click here for Part 2 of our exchange.

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Reading “50 Shades of Grey” as a man must be just like graduating from an Ivy League school: there’s a lot of hype, it’s a grind to get through, and in the end it’s less about what you learned than just being able to say you went there.

Not that I ever had the grades to sniff the Ivy League, but I did dare myself to read and finish “50 Shades.” I took one for the team, because I’m now qualified to answer what guys with better reading tastes may be wondering: “What’s up with that book?”

So, here’s what’s up: You can learn a thing or two about women’s sexuality from reading “50 Shades,” but at over 500 poorly written pages, you may find the return on investment to be lacking. There’s far better erotica out there,  and as dominant-submissive stories go, give me “Secretary” any day.

50 shades of greyThere was a media blitz over the BDSM in the book, but none of Christian Grey’s kinky toys deliver more pain than the writing here. Even mocking it feels too easy, in the same way it’s too easy to make fun of Nickelback’s music. (Yet millions have consumed both products.)

To call this book “controversial” is to give it too much credit. Check out this classic Bill Hicks bit about “Basic Instinct” to know what I mean.

I don’t know who E.L. James is and whether she was intentionally dumbing the book down for a large audience, but this is essentially a Judy Blume novel with naughty parts. The first-person narrative is full of breathless, clumsy prose, and it actually uses the word “magic” as a verb. As in, “I magic a smile on my face and stroll over to the laptop.”

While this high-school-diary style of writing does work better with the sex scenes, which are steamy enough, don’t look for anything too racy. By Grey’s own admission, most of the sex is “vanilla,” and even the characters’ genitalia aren’t directly mentioned, so as not to offend soccer moms from Kansas. If you want some real dirty talk, you’re better off reading James Joyce’s love letters to his wife.

Actually, you’re better off reading James Joyce, period.

But I’m just piling on with the other 30,000 snarky bloggers out there if I continue this way. For what it’s worth, the book is wildly popular with women, so I’ll stick to explaining what a heterosexual man can learn from it:

Women still want to be rescued: There’s been some feminist hand-wringing about “50 Shades” and its submissive view of women’s roles. I think they’re worrying too much. Yes, many women fantasize about being the sub to a sexy guy’s dom … except for those times when they want to do the spanking. Women are too wonderful and complex to boil down to a simple role.

Still, Christian Grey is compared to Lancelot and Superman before Page 100, and much of the fantasy here derives from an assertive, dynamic guy taking a woman into his world. Not just in the bedroom, but also exposing her to classical music and hang gliding.

I’ve seen too many guys try to learn “game” skills without remembering to back that up with an interesting life. This book’s popularity with women reminds us what matters more.

Women can be insecure with guys they’re into: “50 Shades” started out as fan fiction for “Twilight.” And much like Bella, the Anastasia Steele character is meant to be someone any average women can relate to (this video about “Twilight” says it all).

But I’ve known many real-life women far more interesting than her. She’s whiny, as bland as a rice cake and wishes she could be as cool as her hotter, more confident roommate.

In real life, there’s no way Grey seduces Anastasia (or vice-versa). In real life, Grey hooks up with the roommate before ditching her for Miss America. Then again, if Jason Segel and not Russell Brand can end up with Mila Kunis in “Forgetting Sarah Marshall,” the fantasy works both ways, doesn’t it?

Anastasia (ugh, I hate that name) worries until the very end that she’s not good enough for Grey, even though he irrationally goes out of his way to show his singular attraction for her. Having witnessed such insecurity myself, no matter how attractive the women, I can vouch for the realism here.

Women really put the “fantasy” in fantasy guy: So, let’s sum up the Christian Grey character, who ends up falling in love with our plain-Jane female protagonist:

  • He’s hot.
  • No, really, really hot.
  • OMG, he’s so hot!
  • He’s a tall, muscular, 28-year-old billionaire with a mansion, a helicopter that he pilots, and private jet.
  • He’s unfailingly charming and a great listener.
  • He has a large penis and uses it to make Anastasia orgasm twice when she loses her virginity and many, many times over.
  • He’s a virtuoso on the piano.
  • He’s an expert glider and rowing champion.
  • He’s a wine expert.
  • He has a tortured, mysterious past involving lots of women (which of course draws her to him more).

OK, he does have one flaw: He likes listening to Kings of Leon. But otherwise, the Grey character puts Prince Charming to shame. This reminds me of what Roger Sterling says when Don Draper (a 1960s Christian Grey) asks him what women want: “What do they want? Everything! Especially if the other girls have it.”

Women can set the bar for their ideal man pretty high. You don’t need to be Superman/Jesus/Christian Grey, so if she’s placing you on a pedestal, it’s best to disappoint her early so she can appreciate the real you.

Women want you to be dirty with them: A less-experienced guy can forget this. I don’t know why Anastasia and Grey are e-mailing with Blackberries instead of texting with iPhones, but they do give a good sense of the kind of sexual banter women like.

Grey is explicit about how much he wants her and what he wants to do with her, when they’re apart and when they’re together. Women respond more to specific verbal imagery than visual imagery, so it’s worth taking some notes here.

I realize there are two sequels to the book, but I would sooner let Grey punish me with his cat o’ nine tails than read them, so I’ll pretend there is no further story to discover. I’m currently reading some Hemingway to forget this ever happened.

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Going back to basics with sneakers

by GK on August 2, 2012

Some may find the Olympic decathlon challenging, but in the world of GK, there are much greater accomplishments. Like putting together a fly sneaker collection. I have finally done that.

I’ve worked hard on raising my shoe game in general, and I have a sweet arsenal now, but sneakers are where I really wanted to upgrade. I wear them almost everywhere in the uber-casual Bay Area: to work, errands, casual dates or barbecues.

I recently spent my commutes from work doing some online shoe dating, comparing and contrasting the available kicks. I took a close look at some Nikes and Vans. But when my hunt was over, I ended up returning to where it all began over 25 years ago.

The first sneakers I remember wearing were the high-top Converse Weapons popularized by Magic Johnson and Larry Bird in their legendary commercial. I was too young to know better, which is why I wore the purple-and-gold Magic shoes just before I realized I hated the Lakers and loved the Celtics.

Perhaps because of this gaffe, I hadn’t worn a Converse shoe since. I got swept up in the Air Jordan craze soon after, and in my post-collegiate years I started wearing leather “designer” sneakers that might have looked stylish but lacked the too-cool-to-care spirit of what sneakers are about. I stopped that trend last year when I bought some brown, suede Golas that I love and will probably buy again once these wear out.

I’m a big fan of Golas in general — they have the classic low-top sneaker design down, and most Americans don’t wear them, so you’ll stand out here. But I realize now that the DNA of a truly great sneaker must include a canvas top. And no one does canvas like Converse, so it was to her loving bosom that I returned.

I knew I wanted some red-and-white Chuck Taylors, but I also knew I wanted the Converse star-chevron logo on them — it’s the only logo I can wear without feeling like a walking billboard. So I went with the Star Player EVs ($46) that you see at the top.

As the Converse Web site suggests, you should order up a half-size, and their advice turned out to be spot-on. I got a size-10 pair in the mail last week, and I wore them on a first date the same night. I didn’t call the date again, but the sneakers are keepers. They already feel broken in and contrast nicely with blue jeans.

That pair alone would have been a success, but while shopping for those I got an offer I couldn’t refuse: the chance to design my own pair of Star Players. Why other shoe companies don’t let you do this is beyond me, but I stayed up past my bedtime playing around with the feature, and it sold me. You pay a little more for the creativity, but if you’re as particular as I am, it’s worth it.

I ended up filling another need by designing and buying these white sneakers with red details for $70. I just got them in the mail last night, and I’m stoked at how they turned out. I wanted the clean white look, but if you want to go all Roger Sterling on LSD, you have lots of freedom to color the shoes how you see fit.

The shoes came with a surprise detail — when you finish designing them, the Converse site asks for your initials. In my absent-mindedness I thought this was just for bookkeeping, but they actually put the initials on the shoe, as you see here. But because they’re in lower case and on the heel, I don’t mind the extra vanity — they add an understated personal touch.

And really, with all the celebrity endorsements out there, doesn’t the world need a GK shoe?

I really hope I keep my job a while longer, because I completed my sneaker splurge with these Billy Reid for K-Swiss canvas sneakers from J.Crew, giving me the complete red-white-blue, America Fuck Yeah trifecta. The J.Crew site and my local store had run out of the color, but they were able to track down a pair for me in another city. I recommend the shoe in any color — it’s generous with the padding.

It may be gluttony to own four pairs of sneakers, but longevity means a lot to me, and the deep rotation means I should get to spend lots of time with these babies. But for anyone thinking of buying just one pair and beating the snot out of them, you can’t go wrong with some canvas Converse low tops.

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My retirement from coaching and refocus on my career is keeping me away from this blog more than I’d like. The myriad students and memories I accumulated are increasingly morphing into a beautiful-yet-faded dream. It’s bittersweet, but I expected it.

My one reminder that all this stuff really happened is the log of success stories from guys I’ve coached and befriended. A recent example is also perhaps the most inspiring, and I’m going to share his story with you.

Robert is a college student from Houston who’s almost 22. He visited me in March for a weekend of coaching (though retired I still coach the occasional guy), and for extraordinary reasons he explains in the following report, it was a challenge getting him to believe in himself while attracting women. But in the months since, he dedicated himself to getting better at it.

Up until a few days ago, Robert had had sex with exactly one woman in his life. Then, he managed to bed two of them in the same night, and do a mighty good job of it. More important, he learned how to turn his limitations into advantages. Here’s the story:


I was encouraged to share my experience because it really marks how much I’ve grown. I attended a bootcamp with my friend GK in March. Now in July, I feel like that experience has paid off as I’ve continued to grow and grow.

Here’s some background on me: I was born with a mild form of cerebral palsy which causes me to walk with a limp. For a long time I’ve lived with limiting beliefs about myself (ie: I’m not attractive to the opposite sex, my limp will hold me back during sex, etc.). I would always mope and complain about it, and use it as a crutch to say why I wouldn’t succeed with women. Speaking of crutches, since I have a limp, I also use a cane to get around, and would always wonder if girls ever saw me as a sexual being. All of these beliefs put the power out of my hands and into theirs.

I’ve learned something that I want to emphatically share:

It’s ALL BULLSHIT. You are in control of your own life.

Another something I learned: A good haircut can go a long way too. I got a haircut the day before all this happened.

Whatever bullshit people say about not smiling in your pictures is a lie. It’s much better to smile than to play the too cool for school look.

Since working with GK, I have been trying out online dating. My logistics have never been the greatest, and with no car living in the suburbs, I turned online to see if I could somehow counteract that. Needless to say, the moral of the story is you don’t need a car at all. But I’ll get to that.

Up to this point, my online dating ventures had been mixed. I had a couple of dates, a lot of numbers, but nothing really clicked. Having started my profile in early March, I was getting a little discouraged by the whole thing.

My mother recently left me in my house by myself while she went on a vacation. So as luck would have it, one of my logistical issues was solved. I quickly took advantage of it and scheduled a date for Thursday (July 15) with a girl from OKCupid. She seemed cute from her pictures, and we had texted a bit of back and forth. I didn’t have a car, but she seemed willing to come by and pick me up. So I ran with it.

Thursday morning, I get a text from her canceling on me — something about having to babysit her sister’s nephew because the babysitter fell through. My mind is in overdrive at this point, making up all sorts of stories about myself and how I am a failure and whatnot.

Somehow I manage to clear my head, get out of bed, and I text another OkCupid potential. Surprise surprise, she’s willing to hang out with me for lunch. 12:30? That’s in four hours! She lives about 45 driving minutes away, so I know that its a HUGE commitment from her.

So I text her my address and just get ready. My plan A didn’t go down, but I guess I can run with plan B.

Lunch happens and we head back to my place. I’m getting nervous again cause she’s about two years older than me and my mind is making up stories about just about every negative outcome. Breathe, Robert. Breathe.

I remember some of my lessons from the past couple months about escalating and just putting forth myself confidently. One of the things I pride myself on is my musical talents and my penchant to enjoy giving massages. So under the preface of showing her how to play a few songs on my guitar, we go back to my room and I proceed to teach her some chords. After a while, I can sense she is kind of restless and getting bored, so I casually mention that she looks a little tense, and that I am decent at massages…

The rest is history. The top comes off, the massage happens, and then fireworks. We end up cuddling afterwards and watching a movie. She’s a really chill girl and I can definitely see myself spending more time with her in the future. Not bad for a first date!

I figure my day is over at this point (she left my place around 5 p.m.), and I’m just chilling at home, pleased with myself.

At midnight, I get a phone call from a friend of mine. She had just finished going on a date with a guy, and she felt bad about it because her boyfriend just broke up with her about a week ago.

She seemed pretty distraught, and being her friend, I offered her my place for the night so she didn’t have to be alone, promising to keep my clothes on and behave myself. She was pretty adamant about NOT sleeping with me over the phone. Wisely, I chose not to argue.

When she came over about ten minutes later (she drove, again I don’t have a car), she was distraught, and I quickly provided the tissues and the ice cream. I could tell she just needed someone to hold and tell her everything would be okay, so I tried to just do what Anthony DeMello talks about, and that is just to show love to her. We went back to my room and I put on a rom-com (When Harry Met Sally) and we just lay in bed (my clothes were on) and watched the film.

Throughout the film, I watched her expression and constantly provided a shoulder for her to lean on. At this point, I know I want to escalate but I have to be delicate and not be an asshole about it. I had promised to keep my clothes on as well, so I wanted to make her think she seduced me instead. So I decided that the power of simple touch would be enough to put an idea in her mind, so under the covers, I just lightly ran my fingers and hand up her upper leg and thigh. She didn’t protest. I decided to just rest my hand on her inner thigh and see how she responded. She had a curious look on her face when I did that, but she didn’t push me away, and my hand stayed there for the last 10-15 minutes of the movie.

As the movie ended, she commented, “You’ve had your hand over there for quite some time, haven’t you?”  My response: “Yes, I believe I have.”

I lean in a little closer to her so that our faces are almost touching.

“Any guy who keeps his hand there for so long has to be up to no good,” she whispers into my face.

“Well…I guess I am up…to no good…” I say, pronouncing every word in a slight whisper.

She’s aroused, I can tell.  I bide my time and just stare into her eyes, my face half an inch from hers.

“I thought that movie would never end,” she states.

I move in even closer until I can see the texture of her nose. I say, “Why…are you…in such a hurry..?” I brush my nose up against hers, and just stare unblinkingly into her eyes. The tension is palpable.

Then it happens, like we read each other minds. We start making out furiously, my computer cast off to the side, neglected and forgotten. My clothes, once promised to be on, start coming off with alarming speed.

Our sexcapades continued with occasional breaks for meals and cuddling up until 10:30 p.m. THE NEXT DAY. I rock her world (thank you David Shade, Daniel Rose and White Tiger Tantra!!) and she can’t stop coming over and over.

“So, what was that about you not wanting to sleep with me?” I tease her after our second-to-last sex session. She punches me in the shoulder. Those reliable shoulders that she buried her face in. Then she kisses me and we start up again.

What a beautiful day.

The point of this report is hopefully to underscore that anything can happen, even if you don’t plan for it or think its improbable. Don’t make up stories about what you can or can’t do.  For example, the whole being sexually unattractive because of a limp, or your glasses for another; that’s a story that I’ve chosen to buy into.

It might be true, and it might not be true. If I can spin a story in a negative way (ie: sexually unattractive due to limp) I can also spin a story about how she is wildly attracted to guys with limps and has an insane fetish about it and wants to fuck the shit out of it. (In fact, that’s what happened when she picked me up. My cane was in pretty bad shape, and she thought it was sexy that it was so rugged-looking.)

I have to avoid putting my own voice into other people’s heads. Every time I do something positive or successful, however big or small, I congratulate myself in the mirror for accomplishing something that I wouldn’t have been able to do the day before. I never in my wildest dreams would imagine having sex for a good 10-11 hours (with some breaks), but it happened.

I didn’t have to run any patterns, game, or plan way in advance. I just had to escalate, be confident during sex, and honestly, be in the right place at the right time. Put yourself in a situation to succeed and just let things come. And I did it all with no car, a limp, and a beat up old cane. I hope you enjoyed reading this as much as I enjoyed living it.

Much love,


PS: I rescheduled with my original date for a new day this coming Wednesday. We’ll see what happens! :)

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I’ve allowed women in my dating past to write for you before — or even team up with me for a jam session. But never have I allowed a woman I’m currently dating to disrobe in front of you.

That changes today, and what better time for a first time? This week, your friendly neighborhood GK celebrates the 10-year anniversary of his lost virginity. Aside from having to wash my sheets a lot more, the ensuing decade has been a mighty improvement over the previous 25 years.

Appropriately, we will celebrate by going back to bedroom basics. I’m passing the mic to my accomplice tFox, who earned the nickname by being, well, a tiny fox. Though after these photos, she might henceforth be known as Girl with the Dragonfly Tattoo.

For those who would like to get better at removing a woman’s bra with one hand, tFox offers two simple ways (I happen to prefer the first). And away we go:

It’s much more fun to have your clothes taken off you than to do it yourself, so don’t kid yourselves, gentlemen: this one’s as much for us ladies as it is for you.

Like you, women want to keep those makeout sessions moving, and there’s nothing quite like the guy who can slide his hand up your back — lips still locked — and pop your bra off before you even know where he’s headed. Mmmm.

Besides the immediate benefit of being bra-less with a boy, it also signals to us that you’re probably gonna have some game in other areas too, and just the thought of that is hot.

Don’t worry, you’re not raising the bar on yourself so much as setting the tone. I know that a guy who can get my bra off smoothly took the time to learn to do it, which tells me he pays attention. That makes me want to play my cards right, so he’ll spend some of that attention on me.

So with the help of two of my girlfriends extraordinaire, (Hot Face behind the camera and Lolo in front with me) we’ve put together a step-by-step tutorial on two different techniques. Look ‘em over and pick the one you think will be easiest for you.

The Principles

Most bras use an eye-and-hook clasp, with usually two, three or four hooks. When it’s on, the hooks will be on her right, the loops on her left. The hooks latch into only one set of loops, so each technique revolves around releasing the tension (ahem), sliding the hooks out of the loops and then letting go. They’re designed to be quick, so once you’ve got it down, it should only take you a second or two.

Technique One: The Pinch

This technique is less complicated in execution than the Flip, but you have to make sure you’re just pinching the strap, and not your girl. Extra bonus: with a little practice, you can do this one through her shirt.

Step One

Put your thumb and pointer finger on either side of the clasp. You can also use your middle finger, and may have to if the bra has a wide strap with more than two hooks.




Step Two

Pinch the material together so the hooks aren’t pulling on the loops (releasing the tension!). Try to make sure your fingertips are each placed right over the hooks and loops on either side.





Step Three:

Rub your fingers together to pop the hooks out of the loops. You should be able to feel them slide out with a little pop or click. That’s it!





Technique Two: The Flip

This is how I take my bra off. The mechanics are trickier, but once mastered are incredibly reliable. It’s a good one for when you’re on top of a speeding train and need the extra stability.

Step One

Slip your pointer finger under her strap, from above.


Step Two 

Slide your finger to her left, so it goes between the extra strap material that is normally just tucked underneath and the strap itself.





Step Three

Use your index finger and thumb to hold the loop half of the strap, and put your middle finger on the outside of the hook half.

Then, use your middle finger to hold the hook side of the strap in place as you push the loops out from the hooks with your thumb and index finger. (We couldn’t figure out how to shoot that part in a way that would be helpful, but once your fingers are in the right place it’ll be intuitive, don’t worry.)

Success! (GK, in a fit of jealous rage, cruelly censored the unhooked photo. Use your imagination, fellas.)

Study the technique you like best, then ask the next girl you make out with to let you give it a whirl. Maybe even practice a few times with her. Trust me, she’ll think it’s sweet, and nothing beats hands-on (oh yes) experience.

Here’s one sexy song you can play with her:


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Even though I’m having a little fun by calling them sucker moves, I want to be clear: this post is NOT about passing shit tests. It’s not about communicating your Alpha-ness, it’s not about gaining the upper hand with women, and it’s not about winners and losers.

It’s tempting to think in those terms when we’ve been burned by women. Nobody wants to play the fool (even though there’s a great song about it). We would rather win than lose.

It’s just that with enough experience in this game, a man reaches a there-is-no-spoon realization: As long as you spend your time only on women who treat you with common courtesy, and you call out those who don’t, you can’t lose, no matter the result.

And while that may sound a little new-agey, there is also the very practical fact that you’ll get more women — and better ones — this way. Because they’re more likely to respect you if you respect yourself.

Here are a few examples of bad behavior you shouldn’t let women get away with when you’re first going out with them. They’ll help you screen out the good ones from the bad and guarantee you’ll be a playa, not a sucka:

The only time she can see you is while she’s out with her friends: You wouldn’t like it if you booked a five-star hotel and found out it was a hostel, would you? So beware of this logistical bait and switch.

Her friends might be funnier than the cast of “Bridesmaids,” and I might enjoy meeting them. But that’s not the objective here. On a first or second date, I want some one-on-one time to see what she’s about and possibly enjoy some physical rewards if we get along well.

All of this becomes much tougher with her friends distracting her, and usually the kind of girl who would put you in that awkward spot is someone who is socially inept or not taking you seriously. If I wanted to be treated like a secondary friend, I’d go on Facebook.

The smart move: One girl tried this with me after I’d patiently attempted to see her a second time. When I told her why meeting her at a club with her friends wasn’t a good idea, she texted, “Good job of calling me out!” I didn’t end up seeing her again, but that’s the point, isn’t it?

(Parenthetical note: I also apply this sucker move to girls who you’ve already gone out with but are only willing to see you again during day hours or at a venue that isn’t near either of your homes, assuring that nothing sexual can happen.)

She picks out a restaurant and expects you to pay: It’s cliche by now in the advice-giving world that guys shouldn’t take women out to dinner early on. I happen to agree with that cliche, unless you actually enjoy taking women out to restaurants you like and you don’t mind paying. And some women do offer in advance to pay, which is cool too.

Just understand that when a woman suggests dinner, or even drinks, and still expects you to pay for all of it, you might as well just let her reach into your pants and extract your wallet and testicles. Because she already owns them.

The smart move: I cook most of my dinners anyway, so on the rare cases where this comes up, I’ll simply say I have food I need to eat before it spoils, and I’ll make a counter-offer. If she’s interested in me and not the pan-seared halibut, she’ll go along with it.

Even you need to put the phone away, Charlize

You’re out with her and she won’t put her phone down: This one is becoming an epidemic in the pickup/dating world and needs to be treated as such. I’m as hooked on my iPhone as the next person, but if a woman really can’t stick her phone in her purse for an hour without reaching for it reflexively, she doesn’t need a drink. She needs some Ritalin.

The smart move: Don’t get angry or lecture her about it, but do call out her faux pas. Perhaps joke that you’ll confiscate her phone if she doesn’t put it away. Only a clueless or rude woman won’t feel guilty once you’ve done this. And at that point you can pick up your phone and call her a cab.

Letting her flake twice in a row: It’s tempting to be stricter and write her off after she cancels once. I find flakes to be like cockroaches in an apartment: where there’s one, there are probably others. Almost all of my best experiences have been with women who never flaked.

However, sometimes women will have legitimate excuses, just as I’ve had to occasionally cancel for being sick or facing some emergency. So a single-flake with an apology is fine. But to double-flake is simply disrespectful of my time, and I’d rather waste it by watching “Tree of Life.”

The smart move: Tre Tre dealt with this very well a while back. After a girl flaked on him a second time for no good reason at the last minute, he responded with a friendly text letting her know that his time is precious and that he couldn’t let her mess up his plans again, but that maybe he’d run into her sometime at the bar where they met. Of course, she reacted by practically banging down his door for a date, but Tre still refused. He could see the drama that would have awaited.

She rejects your ideas for where to go, without a good reason: I’ve had very few bad dates in my illustrious career, but a classic first date involved this girl who, as it turned out, would only drink Champagne … as in, it had to be from the Champagne region of France. She practically threw a fit at the first bar because they didn’t have it, and she turned down my ideas for other venues for the same reason.

This is an extreme example, but I find that if a woman repeatedly says no to a guy’s ideas and doesn’t offer a good one of her own, this doesn’t bode well for how well-adjusted she’s going to be.

The smart move: It took me longer than it would now because I was still inexperienced, but later that night I told her she seemed more interested in the Champagne than me, and I practically jumped out of the cab we were in. Standing up for yourself is sweeter than any bubbly drink.

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