21st Century Man on…First Dates

Every journey begins with a single step, even one as perilous as finding yourself a mate. In fact, the effort to find someone you can tolerate for the rest of your life is likely to require several distinct journeys, and there is no guarantee that you’ll ever reach your destination. But you’ll try nonetheless.

The key to a successful first date is to convince the object of your interest that you are smart and funny, caring and nurturing, generous and responsible. Moreover, that you have high earning potential and good paternal instincts. That you like to cry at movies and so forth. Of course, only a tiny fraction of men actually possess more than a couple of these qualities, so the first date is more often than not an exercise in constructing a reasonably believable pseudo-you in your date’s mind. A…better you. Fortunately, there are many good strategies for achieving this effect. Most of them will require you to think instinctually about what to do in a given situation…and then do the exact opposite thing. In fact, the more awkward you feel on the first date, the more likely you are to make a good impression. Make this your governing principle and it will serve you well.

Here are some other guidelines to consider whenever you want to make a first date experience more successful:

Prepare for Success
Piss poor planning prevents proper performance. No one plans to fail, but many guys are either too stupid or too lazy to properly plan for the possibility that a date will end up a raging success, thereby ensuring it won’t. To give yourself the greatest possible chance of having a memorable evening, you’ll have to begin behaving contrary to your true nature before you even leave the house. To start with, you’ll have to clean your place. At least a little. At least the bathroom, dude. Seriously. Nothing quashes the amorous inclinations of a young woman quite as hard as using your bathroom and discovering that your toilet has reached puberty. It’s probably not in you to clean anything properly, but you’ve at least got to wipe that thing down with a damp rag, you nasty fucker.

Unfortunately, this isn’t the only prep work you need to do. Women are dramatically less likely to get naked in your presence if they see any evidence that you’ve already seen naked women before. This means you’ll need to put your porn collection away. Also, what’s up with those bikini model posters on your wall? What are you…14? Take those fucking things down already. In fact, you should probably replace them immediately with some Monet prints, which will give her the false impression that you’re a sensitive guy.

Lastly, take all the briefs out of your underwear drawer and burn them. Actually, no. Save a pair or two for pickup basketball and wall ball games, but destroy all evidence of the others immediately. You’ll wonder what the point of boxers could possibly be the first time you scissors your nuts between your legs or have to peel the scrotal bat wings off your upper thighs, but press on, brother. The fact is that boxers have nothing at all to do with male comfort and everything to do with female comfort. Dude, have you ever actually looked at yourself in your tighty-whiteys? Nothing reminds a woman of her father more than you standing in front of her looking like…that, which is, of course, the single worst time for those thoughts to creep in.

What to Wear on a First Date
Dressing properly can be one of the trickiest aspects of first date preparation. If that comes as a surprise, you’re probably one of the 97% of guys who never think about what they’re wearing, in which case it’s going to be even trickier.

In a nutshell, you want to look good……but not too good. You’ll never get away with a simple t-shirt and Velcro sneakers, for example, but a cummerbund or sometimes even just a tie only show that you’re trying too hard. Try to give the impression that you’ve hurriedly and accidentally selected an outfit that happens to look reasonably good on you. But not too good. Like you just rolled out of bed in a pressed, button-down shirt and fashionable, understated slacks, for example.

If you pay attention to the details, the big things will take care of themselves. Details like always wearing dress socks, unless you’re wearing shorts, in which case never wearing dress socks. Or never wearing a hat. Unless you’re balding, in which case always wearing a hat. (Speaking of which—be careful when selecting a hat. You’re not going to pull of the fedora, for example, unless you’re also wearing a suit. And your name is Frank Sinatra.)

How to Behave on a First Date
First of all, say as little as possible. Just sit still and be quiet. The more you say, the more likely you are to say the wrong thing, and by impersonating a deaf mute, you give your date a chance to convince herself that you’re mysterious. Or at least a good listener. You’ll have nights in your life when a date will lure you into a sense of comfort and familiarity. You’ll find her so easy-going and her company so enjoyable that you’ll be tempted to share a glimpse of what you’re really like. This is incredibly dangerous, and you must be very wary of such women.

Many women like to feel respected and taken care of. To support this impression, you should open doors for them and push in their chairs when they sit. You should stand when they leave the room and take similar actions that you’ve never done before and have no intention of repeating once she decides that you’re a gentleman and agrees to sleep with you. Of course, in this century, many women guard their independence and self-reliance religiously, in which case you should under no circumstances do any of these things for them. Many a 21st century woman would rather you fart in her face than push in her chair, so this is either a great or a terrible strategy. Unfortunately, you won’t know which is which until you’ve tried them, so be careful.

Above all, you should be courteous and respectful at all times. Unless, of course, she’s into jerks, in which case you shouldn’t be. If she’s the kind that likes jerks, try to ignore her as much as possible. Don’t open a door for her even when her hands are full of things you’re not helping her carry. Look for creative ways to be inconsiderate. I must warn you that it will be difficult to gauge ahead of time which of these strategies is the great one and which one is fucking terrible, since no Homo sapiens woman has ever admitted to liking jerks. They just do, some of them. Instinctually.

Speaking of women, it’s generally a good idea to avoid your mother as a topic of conversation, lest your date get any impression that you’re a mama’s boy or your mom is a controlling cunt. Or worse. Or…if your date turns out to be deeply family oriented, you probably shouldn’t stop talking about your delightful mother.

Where to Go on a First Date
Any destination can be a winner if you act charismatic and disarm your date with an infectious smile. Of course, you won’t pull either of these things off, so it’s probably best if you stick to a traditional destination.

Dinner can be a great way to spend a date, for example, but only if the food and service are good and several other factors beyond your control align in your favor. It will also require restraint on your part, since it won’t be appropriate for you to eat like a frenzied tiger shark. In fact, you may want to practice chewing, using a napkin and other social dining conventions a couple times at home prior to a dinner date, since you’re probably used to just rolling your eyes back and tearing off giant chunks of meat. Also, it can be helpful to (re)acquaint yourself with the knife and the spoon prior to the big night.

Though they remain a popular choice, movies often make for crappy dates, because they inhibit conversation and make it difficult for the two of you to share eye contact and flirt. For this reason, if it’s going to be a good date, it is inadvisable to spend the night at the movies. And for the same reason, if it’s going to be a bad date, you should absolutely go to the theater. Since you probably won’t know how the date is going to work out ahead of time, you’ll just have to start from an educated guess and hope for the best.

Concerts can be a memorable date destination. In fact, they can be some of the most memorable moments of your entire life. Of course, not all memories are good ones. It’s certainly possible, for example, that your date will become so enamored of the lead singer that you will seem like a distant door prize by comparison. Or perhaps the object of her misdirected affection will turn out to be the hippy with the wonder joints who parks in the same field as you. Furthermore, concerts can lead to dancing, and all dancing is best saved until after you’ve slept together at least twenty times. Just in case.

Active dates can be a novel and interesting means of getting to know someone. Going on a bike ride or meeting for tennis are excellent ways to reduce the amount of speaking you’ll have to do, which, as you know, is always preferable. There are ways you can help to make these experiences enjoyable for your date, too. These include not abandoning them as you pursue an imaginary Lance Armstrong and not pumping your fist and shouting “ha!” every time you score. An active date also gives you the opportunity to assess her figure in those skimpy workout clothes women wear. Of course, the skimpy clothes may be breathtakingly unflattering or she may choose not to wear the skimpy clothes at all, which can cause different kinds of anxiety. Also, there’s all the sweating and the smacking around of your untethered testicles and whatnot. And the possibility that she’ll kick your ass, which can be awkward for both of you.

How to End a First Date
So how does one effectively close? This is the key question. Up until now, your outing hasn’t gone much differently from the last time you went out with your buddy Larry, except that you weren’t holding Larry’s hand and paying attention to his feelings.

Like selling a house, you can’t really say you’ve actually dated someone until you sit down at the closing table and seal the deal, except that the table is more likely a couch or a bed. Or a taxi. Or an ice rink bathroom or whatever. It may surprise you to learn, since it is contrary to your manly instincts, that the first date close is typically more successful when it is a soft sell and involves at least a modicum of subtlety. Fortunately there are other successful approaches, since you likely think the combination of crocs and dress pants is subtle. Keep in mind that you only need a simple kiss to call it an official date. Anything more than that is just gravy. As long as you’ve followed or not followed all the above advice to a T, that stuff will come.

There are over a thousand documented ways to successfully kiss close, but they all have one thing in common. They all require you to disguise the fact that you’re shitting in your pants or otherwise feel like an inadequate idiot. You quite likely are, but this is no time to worry about that. Right now, you are the Lion King. You’re a pimp ass playa. At least until she turns her mouth away and presents you with the cheek. At which point, you should simply thank her for a delightful evening and expeditiously GTFO.

Like every other aspect of the evening, closing is about subverting your natural urges. There’s a chance that the kiss will go amazingly well and take long enough that you’ll be left to decide what to do with your hands. With any luck, one of your arms will be totally numb from being draped over her shoulders all night, but even one hand can get you into some kind of trouble or other. Be careful. This is dangerous territory. You’re up in the rarified mountain air now. Sometimes it is simply prudent to retreat to base camp and re-strategize your ascent plan. It is often in your best interests to thank your date, see her home safely, and go home to break off a hunk into a napkin. Then go review the game plan with your Sherpa buddies.

Then again, there will be times when you’re just minding your own business and your date will actually try to fuck you. This is exactly the kind of possibility few guys properly plan for. Think twice before accepting her invitation to have sex, as this may indicate that she has loose morals, genital piercings or worse. Then, after you’ve given it a proper second thought, accept her invitation and go have the time of your life. With condoms, of course. (Details, people.) Incidentally, if a (first) date ever results in direct genital contact, whether its you getting a tug or full-on porno-style sex on the kitchen counter, understand that you must call your date again within one week…or never, ever again.

Maintaining a Winner’s Attitude
Try not to think of a first date as the beginning of a grueling journey. Try to see it as the possible beginning of the end of a grueling journey. By the time you make it to this point, you’ve likely invested three fuckloads of time and energy getting this far down the path, so try to enjoy yourself out there in the field. Find the perverse joy in even the most awkward bits. Hopefully, by either following or not following all the advice you’ve just received, you’ll find success on your voyage.

Now get going! She’s undoubtedly going to be late, but you have to be there on time or your whole night is fucked.