How To Online Date Successfully

If I was to split my dating life awkwardly into percentages of where I’d sourced dates from, it’d be 75 percent/25 percent erring on the side of online dating. I’m not a bad-looking guy, but I also spent a great deal of my life being quite scared of people until I realized that, in fact, death is certain and, in the end, it’s totally fine to be rejected by a nice young lady, even if you find her attractive. However, online dating combines the convenience of sitting on my ass with the ability to not have to come up with something to say in person, from my face.

After a while on said networks, the most apparent problem came in the face of the damned ratio problem. Though these networks claim to have “fair” ratio splits in which women and men are equally present, that negates the fact that men on these websites are truly awful, that women are consistently bombarded with messages (Tinder skips this, but we’ll get there), and that the men on these websites are actually pretty awful in many ways.

The Annals of Online Dating is probably the most damning of the recordings, but merely scrolling through my timeline I’ll run into a few choice cuts of guys negging and just being straight-up weird with their come-ons. At my absolute kindest, which I engage once every few hours for a minute, I’d say it’s because they don’t know what they’re doing and are simply reading stupid stuff or are getting bad advice. At my most realistic, there are many, many, many, many, many, many guys on these websites looking to get laid as fast as possible who say really horrible, disgusting things to women. I don’t know what sort of fucked up perspective it takes to say to a woman online that you’ve never met—and I quote an Annals of Online Dating message—“Letmegetupondembuttcheeksgirl.”

Don’t immediately jump into sexy-talk. I know. I know you like sex almost as much as you like money, but no girl wants to hear you go straight into talking about your big ding dong and how you’re going to throw a pokéball at her pokémon or whatever it is you say.

Let’s stop a second for the one guy who is gonna say this has worked once, or takes umbrage with this statement or thinks it’s a good idea: Hey man! Has this ever worked for you? What’s your gambit here? Do you think the girl is going to say, “Oh damn, sure, this guy wants to have sex, no guy ever wants that! What a rare opportunity!” In the case of the opportunity above, do you think said girl is going to say, “Mmm, okay, you can get up on these butt cheeks”? Just think about it for a damn second. You’re embarrassing yourself.

Alright, back to the other bad guys.

They do things that, at best, annoy and, at worst, scare women. They are intimidating or desperate or maniacal or just completely dumb. They say nasty things to the girl in the hopes that somehow this will break down her walls and, er, they can have sex I suppose?

Poison like that is stuff you’ll find in The Game and other Pick-up Artistry materials (not gonna link it). And it has got to even guys I’d consider good fellows—a friend in New York extolled the benefits of one book to me about how a supposed PUA picked up some girl who was actually a Playboy model in a Walgreens and they totally did it and it was marvelous. This was a guy who hadn’t had sex in a while and was desperate. There are a lot of these guys on OKCupid and Tinder and the like.

So, if you’re a guy not knowing how to online date, well, here I am to give some advice from someone who has been on plenty of successful online dates, and met someone I fell in love with on Match.com. She’s a model, too! You wouldn’t know her! She lives in Canada!

Some Initial Tips Of Things To Do And Not Do:
1) Your profile should be honest; it should be filled out but not too filled out. (Dude, if it’s a 600+ word profile, that’s an article.) Be blunt, be you, be honest.
2) Now, that being said, don’t put stuff like, “I don’t like conceited girls who are into expensive brands.” Or, “I am a heartbroken man fresh from a terrible, abusive relationship where I was forced to clean the bathrooms eight times a day because she was a nutcase.” Or anything involving the word “bitch” or denigrating women. They don’t like that! Surprise.
3) Conversely, though this will lower your chances (this is a good thing), do feel free to (in short) put your political, social, musical and other likes/dislikes in there as bluntly as you want. If you’re a guy that loves to go shooting, most likely you will not fit in with a girl who is scared of guns, or finds guns bad, or wants to ban guns entirely. If you’re a guy who’s into movies, you probably won’t fit with a girl who hates movies. If you’re a vegetarian, you wanna mention that because it may make a meat-eater unhappy. It may not! But this kind of honesty will save you some time. There’s nothing wrong with you being a gun-toting vegetarian movie-lover who votes conservative; you just want these facts out there so she can say no to them if she isn’t into them.
4) I know it’s time-intensive, but in all cases, read her profile. It’s easy. It’s right there. On the more long-form networks, you’ll find this is more time-consuming. This will become exhausting.
5) Don’t make a form. Just don’t do it. Don’t copy and paste. I know it’s time-consuming, bro, but get over it.
6) Don’t immediately jump into sexy-talk. I know. I know you like sex almost as much as you like money, but no girl wants to hear you go straight into talking about your big ding dong and how you’re going to throw a pokéball at her pokémon or whatever it is you say.
7) Your pictures should be of you, just you, or if it’s a group of people crop it to show you. If it’s a picture of you in a group of four guys, I guarantee one is better looking than you and will disappoint the lady. Note: No pictures of you with your shirt off. The only permissible one I can imagine is that you’re at the beach with your friends. Make this one not your main one. Even if you have a rockin’ bod, that’s not all you are. Don’t lead with that. Don’t even mention it. It should come through in your pictures without your shirt being off.
8) Just… Don’t send a picture of your dick to her out of nowhere. Just don’t do it. I’m sorry, guys, but don’t. I hear tales of this from women way too consistently. Why do it? What’s your goal there? Do you think your dick is some magical divining rod for sex? Do you think it’s a wizard’s wand that magically creates a sex-having situation? Or do you think someone’s having their dinner and PING there’s a penis? That’s what happens. Unless she’s very clearly saying the words “send me a pic of your dick,” in which case, do that I guess? I don’t know.

But seriously folks, here you go.

Tinder is an interesting beast in that there is an insane, addictive immediacy to it.

Tinder, Coffee Meets Bagel, Hinge and Other “Swipe Sites” – The Real Time Chat Apps
Disclosure: I worked with Coffee Meets Bagel a long, long time ago.

Let’s break the above down:
Tinder: Swipe right if you like lady. Swipe left if you don’t like lady. If they swipe right you can chat.
Coffee Meets Bagel: Each day you get a few ladies; you like them or you don’t. You get the chance to try again with ladies that said no to you, and you can also see a few extras each day. The goal is that your Facebook graph is also used to judge why someone wo

uld be better or worse as a fit for you.
Hinge: Hinge uses your Facebook graph to match you with potential ladies who are, theoretically, friends of yours or friends of friends. The result is that you apparently get better results.

I don’t want to go network by network, but Tinder is a valuable place to start as it has some particular issues. Tinder started as a place where guys and girls—according to people who I’m not sure were ever correct—could go to find a “hook up.” I’ve personally rarely heard an actual story of someone who regularly went on Tinder to get someone new to bonk regularly.

Tinder is an interesting beast in that there is an insane, addictive immediacy to it. There’s always a potential girl out there and thus there’s always hope. This is great news, but it’s also a point in which guys get a little, how you say, thirsty. This leads guys to jump straight to sex, as there’s such a feeling of immediacy and, well, hook-up culture within Tinder that they think that’s all anyone’s on there for.

Hinge and Coffee Meets Bagel stick to some of the same principles, but I’ve found people are more open to having a conversation there—the lower amount of choices means that someone is more likely to really want to talk to you versus making just a physical judgment. Someone given one or two or three choices a day is a lot more likely to actually read your profile and look at more than one picture. Perhaps they may like your personality!

I call bullshit on the close to 50/50 ratio on this site, and thus the amount of effort (large, if you want to write a good message) you’re putting in to get actual responses is brutal, and demoralizing.

How To Talk In These Crazy Real-time Apps

Slow down, try and have a real conversation with her, talk to her about her day, ask her about herself. Don’t tell her immediately, “YOU ARE SO BEAUTIFUL MWAH I AM TO LOVE YOU.” Don’t call her sexy. If you somehow feel the urge to say something nice, perhaps say she’s pretty—but even then, why are you saying that? Are you already flirting? Do you know what flirting in textual conversation looks like? Because if you don’t, it’s probably a bad idea (especially in the first few lines of conversation) to launch straight into the “you’re pretty” angle.

This isn’t to say you shouldn’t say it. If she compliments you, compliment her back. This isn’t about women dominating men, but you need to fundamentally understand that women are beset with weird dudes on these apps, many of whom are creepy dudes. Though I’m sure you’ve watched Ryan Gosling smoothly say someone’s eyes are beautiful in some movie sometime, you’re not Ryan Gosling and conversations don’t work with that. Just talk to her, man. Ask her about her day, what she does, if she has a thing in her profile she loves that you love. Talk about that, and don’t force it. If she isn’t responsive for a few minutes, don’t send rapid-fire messages (oh, we’ll get there post-online…), and, by all means, don’t flip out if she stops talking to you entirely. That’s both her choice and, frankly, good in the long run as she probably doesn’t like you anyway, so why bother?

Importantly, don’t go for the “what’s your number” too quickly. It’s a classic error across all platforms that says, “Hey, I want to get you out from the safe, protected zone of online dating sites and onto your personal cell, which is real information about you I can, somehow, use.” I know you want to believe you’re different, and you certainly may be, but have a conversation and say, when it’s clearly going well (ie: She’s responsive. She’s having a conversation that isn’t “lol” or “ok” or you’re doing most of the talking, which might mean she doesn’t like you). Say, “Hey, wanna chat over text?” Perhaps ask her out then get her number.

And now, to the rest of ‘em.

OkCupid, Match.com, eHarmony.com, et al. – The Asynchronous Cabal
Note: I’ve never used PlentyOfFish, because it looks like a website that was built using Frontpage Express.

OkCupid is a good place to start here, as it has one key difference—it’s (mostly) free. You can do extra things if you pay money, but most don’t. The result is it’s a mess with girls constantly pilloried with guys doing exactly what they do on Tinder, but at times far worse, as the girl has put details in there that the guy can then pick apart and say are bad, or use to be creepy as hell. You’re fighting a tide of guys. I call bullshit on the close to 50/50 ratio on this site, and thus the amount of effort (large, if you want to write a good message) you’re putting in to get actual responses is brutal, and demoralizing. You’ll consistently be putting in effort to write good messages to people who will read them (yep, you can see) and get nothing back. Or something back and it’ll go nowhere.

This isn’t to say that there’s no chance in hell. It’s just that OkCupid, for whatever reason, is just that much more competitive for guys. I assume it’s because of the mass of “free” users. The good news is that it’s still a great place to try and date, another option which has in the past been fine for finding dates and potential relationships. It’s just kind of a slog – response rates are lower (I’ve found this and male friends have too – female friends complain about having way too many messages most of which are garbage), and girls that turn on the realtime chat feature generally get 40 guys saying, “HEY HI HI HI HEY.”

Match.com, where I met my current girlfriend (and… an ex or two), in my experience has a higher percentile of people actually looking to date, who want to read messages, who want to engage in a conversation. No, I’m not a shill for Match, as I also met a truly terrible ex on there that one time punched me right in the damn face and had a far stronger punch than I do. It’s costly—$42 a month (there are bulk packages that are cheaper), which I imagine is somewhat a barrier to entry for dudes who want to say, “Mwah hello sweetie I am to make love to you.” When real cold, hard cash is involved, it changes things. I don’t know.

I have never used eHarmony or Chemistry, but I have heard similar things.

How To Write A Message On These Websites

Well, it’s kinda like sending an email. To someone you’ve never met. Someone you potentially would imagine going out with to a place and maybe kissing in the future. However, you wanna get past the “I must smooch” feeling in your underoos and look at her profile. What does she like? What does she not like? Your first message should be with the intention of starting a conversation, so ask her some questions that aren’t “What’re your favorite foods?” And good lord, if she’s mentioned loving books, do not ask her who her favorite author is or if she’s reading anything or read anything good lately. Heck, say some good things you’ve read recently, and if you’re approaching a girl who reads a lot of books that had better not be one of the following (said in the voice of Mr. Plinkett): Harry Potter, Catcher In The Rye, Atlas Shrugged, The Game or any other PUA books, A dating book in general, The Road or basically any generic “everyone probably reads this book, especially a guy” book.

Do you cook? How do you cook? Signature dish? What’s hers—and has she ever tried sous vide or something like that?

I choose this particular example because I’ve seen it a lot. I’ve heard it a lot. “The girl didn’t like me because I said I liked Atlas Shrugged!” “I didn’t know you liked Atlas Shrugged, and now I’m disappointed in you.” “She asked if I read any female authors and I said JK Rowling and she got mad!” “Probably because that’s literally the only female author you’ve read.” “No, uh, you know, there was this one other one sometime I forget.”

And so on.

Basically, you should try and communicate with her as if you were walking up to her at a bar, except you can be blind drunk and vomiting and she’d never know unless you told her!

Don’t do that by the way.

Put together a 150 word message, something short, sweet and easily read that will say to her, “Hey, this guy’s got a brain, but he’s not writing me a letter that reads like a serial killer!” If she’s put YouTube videos in there, watch them, perhaps say something about them. If she likes a thing you like, say something that’s not surface-level (ie: She loves the Foo Fighters, you say you love Everlong; she says she loves movies, you say you love Casablanca; she says she loves food, you say your favorite food is steak). Do you cook? How do you cook? Signature dish? What’s hers—and has she ever tried sous vide or something like that?

I realize these are deeply anecdotal examples, but the point is to start a real conversation with her. Imagine you get sent a random email from a random person asking you to do something (in this case, engage in a conversation) —what would it take for you? The answer is not, I warn you, “She has boobs and I like those.” It’s probably that the person has taken interest in you and has seen things they like and understand and, in turn, wants to talk to you about them, but really wants to talk to you.

Once the conversation continues, just talk, back and forth, roughly in the cadence that she does. Does she respond one sentence at a time? Do the same. Don’t send her a paragraph in response to her one-sentence, and vice-versa. And, just like on Tinder, don’t immediately attempt to get her onto it—It’s an intimidating jump that you don’t want to force on her. Just try and have a conversation. If it goes dead, by all means send one final message just trying to strike up conversation, then move on. Sorry buddy, it ain’t happening.

You don’t want to be desperate in the sense that you don’t want to write some vast, endless novel about her immense beauty and digging into everything she’s written in her profile like an FBI agent.

In Conclusion, And Once You Move Offline…
Online dating is normal now, many years divorced from when it was considered a weird thing that losers did because they “couldn’t meet normal women.” It’s got all the tenets you have of walking up to a girl in a bar and messily trying to talk to her, except much less pressure. None of what I’ve written is to suggest that you, dear reader, are the worst man alive, but there’re so many out there with so many bad habits that I just had to mention them.

Basically, the real core of succeeding in online dating is to be yourself, sure, but also know how to create an actual conversation. You don’t want to be desperate in the sense that you don’t want to write some vast, endless novel about her immense beauty and digging into everything she’s written in her profile like an FBI agent. But you also don’t want to be a brusque, oafish dope that says one line and hopes it pulls her in. Learn to live with the fact that instead of the usual rejection you’ll find at a bar, the girl sort of smirking and walking away, or just saying no, or not giving you her number, you will oftentimes find silence or a general-purpose “No, thanks.” It’s a different kind of minefield. Have fun, I suppose.

Meeting Impressive, Quality Women

When I began this blog, I was fed up with dating, and the quality of women I was meeting. I’m not going to suggest I was always meeting women at quality places (like the café, the library, or at Mensa meetups), but I’m also not going to suggest that quality women don’t frequent the bar or the club. I just knew my chances of meeting the women I wanted, wasn’t high. I continued to enter bad dates and collect horror stories, seeking salvation from any women who would be willing to take pity on my poor soul.

This week, in particular, was filled with meeting very impressive and high quality women, it lead me to ask, “where the hell have y’all been?” The reality is, I wasn’t looking for them. So, what changed?

I would like to point to the Quarterly (a full “report” is coming next week) as the impetus for upgrading the quality of women I’ve been meeting. Every woman at the event was professional, highly impressive, and would make awesome dates. While much credit goes to Paul Carrick Brunson for a great event, it’s hard to think that a speed dating event was the source of meeting great women. I’ve been on many speed dating events, and never have had such a change. This would also ignore the fact that, in the last 2 – 3 years I’ve changed the type of woman I’ve sought. I want to say, I began looking for more quality women when I first met Rule Breaker (who is an impressive, quality woman, even though we’ve broken up), but that would ignore the great women I’ve gone on dates with before her. I would love to think, since Single City Guy I’ve met more of a higher quality woman, but that ignores many of the great women I’ve met before I started this blog.

The more I think about where I’ve met great women, the more I realize, I’ve always met great women, but have ignored them. Some of them know this blog exists (so I might be talking about you.)

There’s many, great, impressive, quality women in my life who, if disappeared into a black hold, would cause me to have a major meltdown. Now, all of them aren’t so single as they were in the not-so-distant past, and I can’t help the feeling of regret as I didn’t even step up to the plate. When I take an honest look at my dating life, I realize there are mistakes that I need to take responsibly for, and learn from. The biggest lesson is recognize, appreciate, and go after the quality women in my life, instead of waiting around. It’s a lesson that you, the reader, should also learn.

Before you begin to meet these impressive women, you need to know how to find them. In order to find these women, reflect on the important women in your life. What are the attributes do they have that you value the most? Why are they so important to you? After some reflection, ask yourself, why haven’t you asked them out on a date? You may be surrounded by the right type of woman, and have never, truly realized it. Great women are found everywhere, you need to recognize them.

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Woman in the Mirror: Age is just a number!

So, my roomie and I decide to go out clubbing last night.  I told her, I have only 27 days left until I turn 50, so I want to take advantage of every day left!  She (being 35) assures me that I don't need to panic.  In fact, she says, you don't look a day over 40.  After all, if you did, people would wonder why I was hanging out with you! Wow, that made me feel better...not.  Anyway, I love to go dancing. . I have been several times in the past 9 months since my separation.  Usually to clubs filled with 20 and 30 somethings, cause well, that's what I "see" myself as. Tonight, we decided to hit a club with an older crowd...30,40 years old and up usually go here.  It is an upscale crowd in a fluent part of town. This club is "the place to be". 

     We walk in the door and it hits me like a slap in the face.  I DO NOT LIKE WHAT I SEE.  Cougars...everywhere.  To my right at a table, two very attractive blonde women who frankly look like a carbon copy of myself.  I see them and think...look at those poor cougars, how pathetic.  Then I think..oh shit...that's ME!  Do I look like that?  and do people think that when they see me?  Then up near the bar, three women who appear to be in their 40's.  They are dressed very provocatively and are very attractive and sexy..  But to me, they seem pathetic.  and scary.  and again I think...is that what I am?    I tell my roomie that I don't like this place and we should head to the club we usually go to, but she refuses.  "We are here," she says. "I don't want to go all the way downtown."  I immediately order a martini..  (I usually drink beer cause liquor makes me a bit crazy) I even tell her, "You know why I don't like this place?  Because it is a mirror of what I am now, and I don't want to be that." She just tells looks at me, a bit taken aback.   I down the martini and order a beer.   I know I am gonna need to drink a lot tonight. 

    So, after a martini and two beers, I begin to loosen up (imagine that) and we do see some friends of ours there.  We go over to where they are sitting and I decide to just get out on the dance floor with everyone else.  Once the music starts pounding and alcohol takes over, I begin to have fun.  Lots of fun.  Just acting crazy, dancing with whoever comes by.  I see everyone else having fun as well.  No, they are not all 20 years old and beautiful.  They are all ages, sizes and colors.  But the one thing in common is that we are all there to meet others, have fun, dance a little, and maybe, just maybe, find someone compatible to hang out with for a while, if only for tonight.  I look across the dance floor and see a beautiful Jamaican man looking at me.  I look directly at him and with the finesse of a cougar on the prowl, begin to lure him towards me.  We dance all night, laughing and having fun with everyone else.  I have no clue if he knows I will be 50 in 3 weeks, and frankly, does it matter?  Age is just a number.  It is how we feel inside that counts.  And right now, this night, I feel free and young at heart.  And if that looks foolish to others....who cares. 

He asks for my "digits" as we leave for the night.  He texts me first thing this morning.  Being as he is just 33 years old, I kindly thank him for his attentions, but tell him, alas, he is too young for me.  But if he ever wants to have fun dancing again, I am up for it.  Yes, age is just a number, but reality is reality.

Don’t Overdo It

While I’m fighting the sharp tingle of a hangover that pierces the back of my head, I’m reminded by a rule I’ve often broken at the Florida club, overdoing it. There’s nothing wrong with going out and getting drunk, but there’s a limit, one many of us have passed in our adventures drinking. I’ve found ways to leave my limits waving to me on the horizon of “this is going to hurt in the morning” road many times. Getting buzzed or a bit drunk is okay, but no one loves a sloppy drunk. I’ve found that many sloppy drunk women are hit on my really creepy men, mainly because they are seen as vulnerable and an easy lay. I’ve also found many sloppy drunk men tend to me more aggressive and dickish, often finding themselves fights or passed out. Yep, this is the cats meow!

There’s nothing wrong with partying, but going to far overboard, while trying to meet someone will cause trouble.

Some of my most interesting nights begin with “at the time I already had 4 beers inside of me.” Those tend to be famous last words as my nights turn into a vibrant haze of crazy drunken foolery, and excitable events. However, I’ve found myself making a fool of myself for pushing my limits. I haven’t done anything I regret because of drinking (well, there was that one time that I gave a chick a lap dance in a chair…), but I don’t ever remember being really proud of my sexual adventures at clubs after being silly drunk.
I also don’t remember going home with someone I respected, wanted, or even cared about while being silly drunk. Most times I’ve gone home alone.

The same goes for my friends, some of them have passed out, other’s don’t remember much of the night, some have had arguments with interested parties. Between helping them find cabs, train stations, or garbage cans, I’m sure the impression they’ve left on others were memorable. I often doubt it. A sloppy, silly drunk isn’t an attractive trait, most men are turned off by it, and most women find it rude. Often, everyone regrets the morning afterwards.

I’m not suggesting people shouldn’t drink or get drunk at the club. I would be a hypocrite. I’m suggesting it isn’t the best mode to operate while attempting to find someone at a club. You’re not going to find the right person while you’re slurring. Mr. or Mrs. Right isn’t going to wait for you. You’re only going to mess up your wardrobe.

Ignoring The Rules

I’ve previously mentioned the rules to dating are meant to bebent. When you meet a person you form a real connection with, often the rules aren’t bent, but broken regardless of the consequences. It’s never a one sided situation, either both people are breaking and bending the rules, or everything is following in their structured manner. I introduced Rule Breaker when I discussed the benefits of being persistent, but that’s not how she earned that nickname, our first date sealed the deal.

“Breaking the rules” means so many different things. First it’s the stereotypical male/female roles that we’re supposed to play while dating. While, in this situation, most of these were rules were maintained, she did break some of them. For instance, she was the one who asked for my number, how many women do this? The second type of rules that were broken are the things you’re supposed to do while dating someone, things to say, not to say, topics that should be addressed on the first date, etc. It was her upfront, honest personality that made me comfortable, as I’m an honest, upfront person. This set of rule breaks I had learned from talking to her on the phone.

Like everything with her, the date did start awkwardly. I arrived early at the negotiated date location, Madame X. I’ve always wanted to use this bar as a date location, just to see how it would work. She was also in the area, so the opportunity had finally arrived. I came to the date with a limited amount of knowledge about her physical appearance. She only had head shots in her profile, and I was in a poorly lit area. It was going to be hard to figure out who’s who. I stood near the entrance and waited, until someone who seemed like it was her was going to walk into the bar or was waiting for someone. A woman did slow down and began to look around. I called my dates name out to that woman, figuring it was her.

I was wrong. “No, I’m her!” A voice I had recognized from my phone conversations said behind me. Obviously it was my date, and the beginning of another awkward, but humorous line of events to follow. Throughout the date, I could not stop laughing and smiling, so much that my checks hurt. It wasn’t any one thing in particular, just the way we talked and meshed seemed to work very well with one another. I don’t think I’ve ever laughed that hard on a date. Ever.

Rule Breaker is an attractive woman, who laid it all out there. I didn’t feel as if I was navigating thru that mental minefield women often put guys thru. She has very varied tastes, like myself, fun, eccentric, speaks off the cuff, and most importantly honest. What surprised me was how attracted I were to those qualities she had. I found her type of honesty sexy, the fact she spoke her mind and didn’t hind behind an excuse. If we disagreed she would give me shit for it, but playfully, and it made me laugh. Another attractive trait she had was her ability to relate to what I was saying, without understanding exactly what I meant. I’m a geek, and made a few geek jokes – one was calculating the differences in ages between me and my siblings. It took me a moment to remember the age differences because at any given time there’s an additional year difference. I joked it was like computer code, and made a code joke (“if before the month of April but not after the month of June relative to the suns positions based on the hypotenuse of y then minus….”) She’s not a coder at all, but understood he joke, and participated! She later said, “I don’t get it, but I get it!” The same thing occurred with a sports references I made. While I’m very attracted to women who love sports, she’s not a sports fan, but makes sincere and honest attempts to get the reference. That blew me away.
As I got to know her better throughout the evening, I realized that Rule Breaker was the type of woman I’ve sought for, but have passed up in the past. Not because I wasn’t attracted to them, but because I felt so comfortable with them they would become dear friends of mine. She reminded me of a few friends, all whom I wanted to hook up with, and I realized I wasn’t going to make the same mistake with her that I have with other women. I wanted to see her naked at some point, and had to be sure I made that fact known. As that thought went through my head, I was reminded of something Thomas and Laurie taught me, introducing some sexual tension.

To introduce some form of sexual tension with a woman, you must do it with touch. This should be subtle, say by touching her leg or arm. Not a poke, but more like laying your hand on her leg while making a point. I did this repetitively throughout the evening, all naturally and not frequent enough that it got annoying. She responded a few times with her own touches on my leg or hands, which made it feel as if I was on the right track. It was clear that the signals were sent, we both like each other!

After a great date, two drinks, it was time to go home. I walked with her to a train where we separated and went our separate ways. She went uptown, I went downtown. We hugged and parted, and tentatively set up a date for the next week. Moments later I was kicking myself a bit, I wanted to kiss her. I was going to have to make sure that happened on the second date, which meant calling her soon.

Improv Dating Tips

Dating, for men who are not handsome or rich, is the process by which a man slowly tricks a woman into sleeping with him. Blame evolutionary biology. Rich men who can provide lives of safety and comfort. Every molecule in a woman’s body has evolved to resist the poor, average-looking guy. As a result, the average guy must resort to trickery so that he can remain in a woman’s life long enough to prove that he has value. (The average guy often proves to have more value because a man who has been rejected repeatedly is more grounded than someone who seldom hears the word no. At least, this is what I learned from every 1980s movie that resolved its central conflict with a ski race or a regatta.)

There are many tricks a man can use to gain a woman’s interest and some of the best come from the world of improv. I know from experience. I have performed improvisational comedy since 2006, having studied at the Upright Citizens Brigade in Los Angeles. Last year I noticed I was, unconsciously at first, employing many of the lessons learned from improv while on dates. I should not have been surprised. A good improv scene contains many of the same virtues as a good date – agreement, spontaneity and fun.

1. Yes-and

This is the first rule of improv. (OK, there are no rules of improv – they can all be broken – but there are choices that produce, in basketball terms, high-percentage shots. Consider each rule a high-percentage shot.) Yes-and means that you take whatever the other person says, agree with it, and add a piece of information. It is a great way to keep scenes and conversations moving, and it inevitably leads somewhere unexpected. That does not mean you should agree with everything your date says. Just remember that if you disagree, you are going to have to reset the conversation and bring it somewhere fun again. That takes effort. You can do it, but wouldn’t it have been easier to keep the original conversation ball rolling?

           

2. Remember the and

The and is the important part of yes-and. It is your imprint on the conversation. If you just keep saying yes, you’re going to bore her. If you add interesting ands, she will see that you have your own point of view, and since you just agreed with her, your point of view in some way corresponds with hers. The conversation flatters her. (I know Mystery Method says you should tease or “neg” women. There is a time for that. But you need to back off when you are building trust. The hard part — meeting her — is over.) The great thing about and is that you can use it to make yourself look strong, smart or altruistic. Remember, you are trying to trick her into thinking you have value until she realizes that you do, like when Beth finally chooses Lane at the end of “Better off Dead.”

                       

3. Avoid questions

It’s a date. You have to ask questions, right? Sure. But not too many. Every time you ask a question you create a personal void in the conversation. A man who asks too many questions does not create a solid impression of himself. His date does not know what he is about. If he cannot communicate on the first date – when people are eager to please – what will he be like on date 15? Ask only the most essential questions. Otherwise, offer information about yourself and leave opportunities for her to do the same. Think of it this way. A woman who answers repeated questions is doing all of the heavy lifting, just like an improv actor in a scene is doing all of the thinking. Do you think that is fun for her? Or do you think she would have more fun laughing at your stories?

4. Focus on the moment

In improv, it is a poor choice to talk about characters who are not onstage. The higher-percentage shot is to explore your relationship with your scene partner. It yields more gratifying results. The same holds true on a date. Rather than talking about other dates you have been on, or other women whom you have dated, or people whom she has not met, focus on what makes the date that you are on unique. Because it’s a date, something weird is bound to happen. In improv we call that weird thing “the game of the scene.” On a date, that weird thing becomes your first inside joke. It’s your go-to when the conversation drags and possibly the joke yourbest man will tell at the reception if you get married. You will recognize the game of your date if you are focused on the present moment.

5. Be specific

The biggest laughs in improv stories often come from the details. The first scene partner says, “Hi, officer, was I speeding?” The second scene partner says, “Yeah, you were doing 85.” The first scene partner says, “I had no idea I was going that fast.” Then the second scene partner says, “That’s because you’re driving a horse and buggy.” The punch line is in the detail – the horse and buggy. (I know that example is not funny. There are few things less hilarious than describing an improv scene. My apologies.) My point is, provide details. It is how she will remember you, especially when she talks to her girlfriends. And yes, you want her talking about you to her girlfriends. It means she is thinking about you. So give her details. They’re hilarious and endearing. Handsome, rich regatta-losers, like Teddy from “One Crazy Summer,” are neither.

Three Reasons All Guys Should Go Down

If my inbox is any indication, men are, when it comes to oral sex, letting down the side.  Apparently, far too many men think oral is a one-way street.  So, I'm going to do my best to correct this: ladies with gun-shy men, grab them, sit them down, and make them read the following reasons:

Any Complaints You Have, She Has, and She Does It Anyway

One complaint about going down on a lady that I've never gotten is "I don't like the taste."

You don't like the taste?  Are you kidding me?  What do you think yours tastes like, rainbow sherbet?  Do you even bother to scrub it before you ask her to put it in her mouth?

Another problem some have are the power dynamics, which I frankly am not qualified for (see a psychologist), but frankly, a little head is not going to kill you.  Grow up.

It Is The Easiest and Best Foreplay You Will Ever Perform

Seriously, oral sex is probably the simplest, least complicated thing you will ever do when it comes to sex in your entire life short of whacking it.  Granted, foreplay in general is fairly easy (provided you listen to your partner), but this is a walk in the park.  Five, ten minutes and you're good to go.

And it's not like it's complicated: the nice thing about groins is that pretty much anything you do down there that doesn't involve teeth will feel good.  True, there are techniques women appreciate (what guys do in porn?  Don't do that), but overall, it's a fairly simple thing.

Finally, it really does make sex easier.  Many women are incredibly aroused by it, which means anything else you want to do is about 1000% easier to pull off.

It's One Of the Key Foundations of a Relationship

Well, not oral per se, but rather what it implies: common courtesy.

Being selfish in a relationship is going to cause problems sooner rather than later, whether it's blowing off a meeting with her sister or demanding she do things that you refuse to in bed.  A lack of courtesy can screw up even a casual relationship: why would a woman keep hooking up with you if you refuse to give her what she wants or needs sexually?

So, develop some common courtesy: it'll pay off, and not just in bed.

OK, especially in bed, but there are also side benefits.