Podcast with Rob: Online-Dating Profiles

by GK on February 22, 2011

They say that in advertising, we are the product. At least that’s what Don Draper said in one episode. This is all the more true when it comes to writing an online-dating profile, when we must do what many of us despise: sell ourselves.

I don’t think a man’s written profile is the most important factor in attracting women online — pictures are probably more important — but a confident, articulate self-description can only help his chances. To that end, Rob Overman broke down a mediocre profile written by his former student and added some subtle shine to it.

Here are some issues Rob and I cover:

  • What your profile can say about you — good and bad — to prospective dates.
  • Writing a profile that flatters you while not getting too serious with it.
  • Why younger girls might not respond if you paint yourself as the funny guy.


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As part of Online Dating Month, I’m linking to a site I’ve studied since beginning my little Match.com experiment. OK Cupid, a free dating site, maintains a blog updated with compelling, if not bulletproof, statistics about what its users find attractive. You can question how they compile their data, and my analytical friends have, but it’s a match made in heaven for us nerdy singles.

 You can give the site a spin and look for the posts that catch your eye, but here are a few I like:

The best questions for a first date: Sent to me by my buddy Tre Tre. The data links serious questions we’d like to ask a prospect with casual questions that reveal the same answer about her. My favorite: If she likes the taste of beer, she’s far more likely to consider sex on the first date.

Race and response rates: It’s a touchy subject and some may take issue with it, but according to OKC’s data, white men and women hold more of the cards in online dating. Not that I’m surprised to see that.

The 4 big myths of profile pictures: The one myth that caught my eye revolves around men and what facial expressions they should have in their photos. According to OKC’s data, they’re better off looking away from the camera and not smiling. I showed this to my compatriot Rob Overman, who argues the opposite in our recent podcast, but he’s sticking to his guns on this one.

Meanwhile, my personal data gathering continues.

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I’m old enough to remember a time when online dating was this new, semi-taboo novelty. It was seen as a bastion for awkward singles who couldn’t find a date in person. Which, coincidentally, is when I first tried it back in the late 90s/early 00s.

Now, in tech-crazy San Francisco, I’ve been considered weird for not dating online, and I’ve resisted it for years, just as I resisted getting a smartphone.

Well, I caved in and bought an iPhone this week, and for the last month I’ve been dating on Match.com for the first time. This was in part inspired by a former student of mine who offered to sponsor my three-month subscription, in return for my analysis. But also, it’s just been something I’ve wanted to try.

I’m a month into the experiment now, and my very non-single friend Rob is joining me to discuss it with some podcasts. In this first installment, we’ll delve into the following:

  • How easy it is to be overwhelmed by online dates in a big city like mine.
  • My complaints with the clunky Match Web site, and why I feel like a stalker on it.
  • Some tips I’ve learned about having a profile that stands out and sending interesting messages.
  • Why Rob wants to see me smile.

We’ll have more podcasts later. Oh, and perhaps you can help us with something: We’re trying to think of a snappy name for the podcasts Rob and I do together, and we’re coming up blank so far. So if you can think of a title that’s witty and not obscene, do let us know.


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I’ve had female friends most of my life and currently hang out with a gaggle of them. Rob Overman has had one female friend his entire life and considers them a waste of time.

We thought this would be a great subject for a podcast, and we spent the better part of an hour debating it. Ultimately, I don’t think there’s any right answer for every guy — it’s just whatever feels right to you. I’ve had some very fulfilling platonic friendships with women, and the sexual tension that may linger in them is no big deal to me. But if you’re like Rob and don’t want to deal with that crap, that’s fine too.

You’ll hear us discuss the following:

  • How Rob’s wife is already betraying him.
  • A tribute to Dirk Manley, who should have been part of this podcast.
  • The benefits to being friends with girls, as well as the dangers.
  • Why it’s better to meet women when I’m hanging out with guys.
  • An invitation for guys to contact us if you’d be interested in a call-in podcast.

You can play the whole podcast here, but we recommend you download this so you can listen to it anywhere.

Rob and I have more podcast collaborations in the works, so stay tuned for some madcap fun.


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Settle down, class, because I’d like to introduce you to the new girl, and we’re going to try something different at Club GK.
Joining us today for an e-mail exchange is Tall Anna, aka Freebird No. 4 from a previous post. We had one date together, and I can’t promise I won’t hit on you again someday, but I’m happy to have you as a rad female friend (stay tuned for a podcast with Rob about this very topic). How tall are you again, Tall Anna?

ANNA: 6-foot-1! Well, actually, it depends on who’s asking. Technically, I’m 6 feet and three-quarters of an inch. My online dating profile will tell you I’m 6 feet even, but in general conversation, I tend to round up and say 6-1. When I was 14, my orthopedist told me, after looking at X-rays of my growth plates, that I’d grow up to be 6-2, but I’m hoping I’ll get that extra inch only in my patent leather heels and not an awkward, late-20s growth spurt.

Thanks for letting me blog crash, GK. I’m definitely happy our night of boisterous dancing and an attempted date turned into a budding friendship sprinkled with picnics on the beach, international travel storytelling over cappuccinos and, of course, even more dance parties.

So, you’ve done a solid job of providing your readers (and admittedly me, on occasion) with some sound dating and getting-yourself-out-there advice, but I think there’s something to be said for the female perspective.

I’ll say this upfront: I’m not an expert, but I am an extrovert who has spent quite a bit of time over the last 10 years crushing over, talking to, dating, sleeping and living with, writing about and giving a plethora of advice to the male persuasion. I guess it’s also helped that my mom’s a couples therapist and sex educator, and I’ve grown up comfortable talking about stuff most people would never talk about with their parents, let alone at the dinner table or on a first date.

So, I’m here. I’m all ears. I’m not afraid to let you guys know what of GK’s advice is spot-on, and perhaps that which makes my eyes roll. In any case, I hope I can help.

Where are we headed today, GK?

GK: Well, I’m headed for a date in a few hours.
Oh, you mean for this article. I’ll get to that in a minute, as I ponder how gay you’ve just made our friendship sound. First, I wanted to say I’m honored to have you here as a contributor. Six-foot-one, volleyball-playing blondes who have written about dating and sex don’t exactly grow on trees, and I think you’ll have some great perspective to offer — not just for our readers, but for me as well. Even though I’m never wrong. At least not for the last 10 minutes.
Anyway, for our first collaboration, we’ll be talking about statements vs. questions. If you know about the Big Four that Rob and I are into, you know that we’re big on a guy talking about himself when he meets a woman. But when you and I were having coffee the other day, I believe you had a dissenting opinion on this. Correct?

ANNA:  I did, indeed.

When I first read your post about the Big Four (and yes, I may have been Internet-stalking you at the time), I got the sense that you were advising these guys not to ask questions.

No questions?! How the hell am I supposed to know that my date’s interested in who I am, and not just interested in himself, if all he’s talking about is how cool he is? What — am I supposed to just interject when he goes to take a breath, or pauses to remember the name of his hot scuba guide from last summer’s trip to the Great Barrier Reef?

Questions, to me, express genuine interest in the person, show that you’re actually present on your date (and not off in la-la land thinking about the girl you made out with the night before), and show that you’re not simply a narcissist. I’ve dated a no-questions-guy once, or as some of my friends and readers know him, Man #11. I’ve never been on such one-sided, exhausting dates: all him, no me, all the time. There should be a balance, you know?

GK: Funny, I’ve been talking about the Great Barrier Reef ever since I got back a month ago! Alas, I had no hot scuba instructors there.
You’re absolutely right about needing a balance between statements and questions. And any guy who does nothing but talk about himself is better off masturbating while reading a Shakespearean monologue than spending time with you. But here’s why I prefer it in the Big Four:
Yes, questions can show genuine interest. But if I’ve just met this woman somewhere, or on a first date even, and she doesn’t know GK from GQ, I’m less likely to get genuine answers from her. When I first got involved with Charisma Arts, a lot of their students were mocked for asking girls they just met, “What’s your passion?” Indeed, I found that when I tried it, I’d usually get a shrug or some weak answer from her.
Then I’d try asking another question. Another weak answer. Suddenly, confused on what to talk about, I found myself asking what we call a Question Train. But the destination for this train is usually, “Well, I’ve gotta go.”
And perhaps “what’s your passion” is just the question you wanted to hear from Man #11. But that’s because he was no longer a stranger. And nothing de-strangerfies a guy like offering details about who he is. Then, if she can relate to him, his questions will mean a lot more.
Oh, and I’d be remiss if I didn’t add this. You did sleep with that guy, so he must have been doing something right.
Maybe this is where online dating and offline dating differ. Perhaps Man #11’s profile already revealed his guitar-playing or passion for his career (though I’m guessing he saved the self-love details for later), so he felt like less of a stranger on your first date. I’m less experienced online, though I do have my second-ever Match.com date in two hours. 
ANNA: Whether you met online or off, I think it comes down to what questions to ask and when.

I’m totally guilty of the nervous question asking — my natural response to a slightly uncomfortable date situation. Because people love to talk about themselves, and it’s an easy thing to lean back on to get the ball rolling. At least it’s better than nervous rambling.

Before a girl is going to open up to you, she needs to feel safe doing so. Safe from judgment, from mocking, from the sarcastic eye roll or smirk. This is definitely where talking about yourself helps set that tone.

Be genuine, and she’ll reciprocate (hopefully). Share about you, and she’ll share about her. Sometimes, though, she might be a little nervous and uncomfortable regardless of the made-up, at-ease face she’s wearing. Giving her a little prompt — conversational hand-holding, per se — is a good way to ease into naturally flowing conversation.

So yes, setting the tone with some witty, or at least entertaining, storytelling is a prime foundation for connection and relation. But if you have the floor, don’t forget to share it. After a bit of monologuing, offer your date a chance to pipe in with a question that relates to what you were just talking about, what you like about her, something you’ve observed or, in the case of online dating, what you remember reading about her.

Perhaps: “So, do you have any scars with funny stories behind them?” or “What are some of your favorite spots around the world?” Or gently touch, or caress, her wrist and ask “So tell me about this bracelet.” 

Questions not to ask, however, especially out of the blue:

  • What’s your passion? (For what? I only get one?)
  • What drives you? (To do what? Get out of bed in the morning? To create the Pandora stations I do? To write excessively long emails? To live until tomorrow?)
  • What’s your philosophy on life? (You will want to know this sooner or later, but let the answer reveal itself naturally through getting to know her better rather than putting her on the spot. Best to keep it a little more light-hearted at first.)
  • Where do you see yourself in five years? (What is this a job interview?)

I’ll give it to Man #11. He was a good storyteller. And obviously, something about it worked. Mind you, only for a little while. It’s just that there comes a point where I want to story-tell, too. And if my date keeps talking about himself, and only himself… well, the destination of that train is “Well, I’ve gotta go.”

GK:  I have to say, you beat me to the punch when you used the words “set the tone” in regard to statements. That’s exactly what I was going to say. When done right, it’s sort of like the intro to Michael Jackson’s “Billie Jean.” Within 15 seconds, you know exactly what you’re getting: the awesomest pop song ever. 
And I agree with everything you said about right and wrong questions (Just Say No to passion). If she seems interested in something I said, I’ll often turn it around and ask her about it. When I hear her respond with, “Good question!” as she did the other day, I know I’m doing something right.
Hmm, after all that fussin’, it sounds like we’re kind of in agreement: Saying relatable things about yourself and telling a good story are great ways to help a woman understand you, and then it’s a good idea to ask genuine questions of her so you can understand her better. Does this sound right to you?

ANNA: While I may not agree with you that Billie Jean is the best pop song of all time, I definitely do agree with you on the rest.

Mutual understanding and having the right vibe are crucial. Anyone who’s read Malcolm Gladwell’s “Blink,” or has any sense of intuition, knows that in the first few minutes — seconds, even — you can tell whether or not you’ll like a person. (It’s for this reason I don’t think the first kiss should be at the end of the date but rather in the middle of it. But more on that in another post.) And getting to know her through an exchange of stories and questions is a good way to confirm whether your first impressions are spot-on or way off.

GK: Well, as experiments go, I think this one was pretty damned good. I hope you guys enjoyed it, and I look forward to having Tall Anna back for some more experimentation. Whoa, that sounded wrong.

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I’ve said it, and so have so many others in the advice-giving game: Be Yourself. It’s so vague yet so right at the same time, and the gap we must bridge to explain it can seem wider than the Grand Canyon. What if we don’t know ourselves yet? What if yourself changes a little bit from day to day?

And what if who we are is simply unlikeable to many people? Should we be ourselves then?

I was reminded of the latter question after watching the Bears-Packers playoff game Sunday. For those of you not familiar with American football, Jay Cutler is quarterback of the Bears, and I hate him. I hate him worse than a bad rash, spoiled milk and high school geometry put together. Have I ever met him? Do I know much about him as a person? Nope.

But from all accounts, and few are denying them, Cutler is an arrogant, aloof prick who doesn’t care about much of anything. He especially doesn’t care about being liked. And some might consider that an admirable quality, even though most of Cutler’s peers dislike him. We’re not supposed to care what people think of us, right?

Right. Kind of. But there are consequences for not being liked, and we saw them play out during and after the game. With a Super Bowl berth at stake, Cutler didn’t play most of the second half after his knee was injured, and the Bears lost. We wouldn’t learn until a day later that he had suffered a sprained knee ligament, which is serious, though some players have performed with similar injuries.

But with TV cameras showing Cutler walking and standing alone on the sideline with his usual bad body language and what looked like iPod earbuds on, many of us wondered if he was quitting on his team. And I don’t just mean fans or journalists; I’m talking about Cutler’s fellow NFL players, who flooded Twitter with derisive comments questioning his toughness.  

As much as I wanted to see Cutler lose, this kind of harshness from a player’s peers was unprecedented and probably unfair. Cutler may never live this down, and I’m sure Peyton Manning or Tom Brady wouldn’t have been bashed like that if they were similarly hurt.

Understanding a player’s injury is complex, but the reason for his rough treatment is simple: people don’t like Jay Cutler. And people who aren’t liked often lose the benefit of the doubt.

I consider this food for thought, considering every guy I’ve coached was coming to me because he wanted to be liked. I know I’ve benefited greatly from being liked. I’ve been promoted at work and introduced to women because of it, and I saved on half my vacation costs to Australia and Asia last month because of help from friends (at least, I think they like me).

In contrast, I’ve been laid off from a job in part because the guy making the decision was friends with another employee, and I’m sure I’ve lost out on women because their friends had bad impressions of me.

Some might say it doesn’t matter if you’re liked or not; it only matters if you’re respected. Maybe, but only if you don’t need help. People respect Barry Bonds as one of the top five hitters in baseball history, but now that he’s been linked to steroids, reporters may never vote him into the Hall of Fame. Because he treated most people like cockroaches.

In some cases, you can be disliked and still handle adversity. Kanye West is giving toasts to douchebags like himself since the Taylor Swift fiasco, but he’s also a douchebag who wears his flaws on his sleeve. Because of this, even his critics can relate to him. He also put out the best hip-hop album of 2010, which helps. 

Jay Cutler could have helped people relate to him by giving interviews or revealing himself more. He could have improved his image by pretending to limp in pain on the sideline after his injury or given some fiery speech to his teammates on the sideline. But that wouldn’t have been true to his nature. Ironically, being himself made him much less likable.

Does that mean you should act like someone you’re not just to make someone like you? I think it’s generally a bad idea, but only you can decide where to draw the line and decide what’s more important. Willy Loman thought being liked meant everything in “Death of a Salesman,” and he just ended up living a lie and killing himself because of it. 

On the other side of the spectrum, I think of the first episode of “Mad Men,” when young, ambitious Pete sexually harasses Peggy on her first day (people didn’t get fired for that in 1960), and Don tells him that if he keeps acting like that, “you’ll die in the corner office, a midlevel executive with a little bit of hair who women go home with out of pity. Want to know why? Because no one will like you.”

Of course, chances are you’re way easier to like than Jay Cutler, and to be liked, all you often need to do is show people you like them. That’s why it’s one of the Big Four! But I had to bring this up.

I’ll get around to my hatred of LeBron James some other time.

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In Memory of Dirk

by GK on January 19, 2011 · 9 comments

 This post won’t be as long as I originally expected. I’d rather avoid a lot of the “seize the day” cliches that come from an untimely death, and I’ll just stick to my personal thoughts about Dirk Manley. It is neither desirable nor intentional that I already had to give a eulogy to a departed friend exactly one year ago, and you can find a more inspirational entry there. Combined with the loss of my good college friend three years ago, I’m getting tired of mourning.

Like most of those who followed Dirk’s writings, I never met the guy in person or talked to him on the phone (though I was about to for our podcast). I never even saw a picture of him. So why did I feel enough of a kinship with him to shed a tear at the news, or think of him when I was in Manly, Australia, last month?

I saw a lot of myself in Dirk. Before his blog, I’d admired him from afar on the now-extinct Charisma Arts forums — he was one of the few guys giving advice there that actually seemed to be grounded in personal experience, not theory. And he just seemed like a cool guy. So I finally PM’d him and started a correspondence between us.

It turned out he was a shy only child like me, a late-in-life virgin like me, a writer like me, and went to school in Southern California, like me. Even his writing style and advice resembled my own, to the point where I thought I might have a body double in Kansas.

It impressed me that despite being so generous with his advice, both on the forums and his blog, Dirk was never looking to become an instructor or sell anything. He really just wanted to help guys, and guys listened to him because of it.

I’m glad that Dirk contributed a guest blog, which happens to be one of the most popular posts on this site. When I think of Alec Baldwin and Always Be Closing, I’ll think of Dirk. I only wish we could have collaborated more together. We were days away from recording a triple-team podcast with Rob, and the two of us will continue the podcast as planned to pay tribute to Dirk.

Dirk never represented a method to me, just a way of being. And in the post-Charisma Arts coaching world, I was glad to have a guy out there preaching the importance of unapologetic courage over game. I’m saddened not just by his loss, but that guys will have one less place to turn to for solid, healthy advice with their social and seduction lives. This is a community of strangers taking life lessons from strangers, and it’s no different with me or Dirk, though I’m sorry to see one less role model out there.

But for those of you who read Dirk, consider yourselves lucky. You know what you need to know, and I hope his blog remains online so that others can be influenced by him the way we were. You have a chance to think of him whenever you get nervous about a risk with a girl or something else, and you have a chance to make his spirit proud by feeling that nervousness and taking the risk anyway.

Oops, I’m getting a little inspirational there. Bad habit of mine. Anyway, I will miss you, Dirk.

If you have a story of how Dirk inspired or helped you, I’d love to see it in the comments.

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The News about Dirk Manley

by GK on January 16, 2011 · 7 comments

This has been a painful day for me. Earlier today, I read a blog post regarding the apparent death of my friend and fellow blogger, Dirk Manley. It appears to be written by his girlfriend and explains that Dirk was killed by a drunk driver while walking home.

Dirk, who has guest-blogged for me and whom I’ve admired since my Charisma Arts days, was days from recording a podcast with me and Rob — in fact he had e-mailed me about it just hours before his apparent death. I don’t have a phone number to call, so I can’t confirm the news, and I pray this is just a bad joke, but it looks real to me.

I haven’t collected all my thoughts about this yet, but I’ll have more to say in a couple of days. Until then, I mourn the loss of a great guy.

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