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Of all the phases of courtship, this one is undoubtedly the most complex, variable, and failure-prone. It can last as little as a few minutes or as long as years. It's bounded on the front end by the pickup (see The Art Of The Pickup). It's bounded on the back end by a decision to have sexual intimacy, which seriously changes the stakes in the relational game (and, among other things, makes a sudden evaporation of the relationship rather less likely).
If the whole concept of dating makes a panic-sweat pop out on your forehead, you have my sympathy. It's a minefield all right. The pickup thing and actual sex are both actually easier if you've got their basic moves down; those behaviors are half-instinctive and don't show a lot of variability, comparatively speaking. Men and women have been picking each other up and bedding each other down in much the same ways since the Bronze Age -- but dating has been through dizzying changes even in this century, brought on by the second-order effects of changes like the automobile and the contraceptive pill and the AIDS scare.
Perhaps it's not surprising that leading-edge cultures seem to be showing a tendency to seriously compress the dating phase, shifting a lot of the getting-to-know-you-stuff into either pre-pickup social interaction or the early stages of the sexual relationship. The `classic' first date that starts out with the two of you knowing almost nothing about each other seems to be in decline, which is probably a good thing for the nerves of all concerned -- and the blind date, long a staple of comedy routines, seems to be almost extinct. The experience one of my beautiful geekgirl assistants reported in a previous essay is an index of these trends:
Amy: "He finally asked me out. I didn't leave his apartment for three days following that date. Get the picture? "
So maybe the best tip for successful dating is to do it with somebody you already share context with -- a peer at work, or somebody you've met through and been briefed on by a friend, or somebody you've gotten to know a bit through one of the special-interest group activities often connected to hackerdom (like a Linux user's group meeting, SCA or Renaissance Faire event, neopagan festival, martial-arts class, SF convention, IRC channels, etc.)
Maybe the optimum setup for the both the pre-pickup getting-to-know-you and the pickup is a full-weekend event like an SF convention or SCA revel or neopagan gathering. The festival atmosphere helps de-inhibit people and the shared interest gives you something to talk about. If you're lucky you may find a partner, get to know the person, do the pickup script, drag each other happily off into the bushes, and effectively skip the awkward dating thing entirely.
Cathy: The "shared setting" does more than ease inhibitions and make it easier to talk; it makes it easier to separate yourself from the person in question if things start to go sour.
Let's suppose you can't manage that, though. OK, guys, what do you do in the conventional dating situation? The answer isn't complicated. Something fun! And, since you're a hacker, something that supplies the two of you with a conversational topic and stuff for your brains to interact about. The standard-issue bar or club scene tends to be a non-starter for us -- but you shouldn't feel bad about that, it just means we have functioning brains and the women we date tend to have them too even when they're not geekish themselves.
Amy: "Bars are almost always too loud to allow for any conversation. If you must take her to a bar, club, concert, etc., be sure to include a quiet activity like dinner, too, so that you can actually chat. After event cocktails or munchies can be a very nice way to wrap things up and talk about the noisy event you just experienced together. It's smoother than just inviting her up to your apartment directly afterwards..."
More generally, as a hacker or geek you are best off dating a woman who's as intelligent and stimulated by novelty as you are. This should affect how you plan a date. It also means that you should be able to ask her to plan a date that both of you will enjoy, and this might be a good idea for the second one. For better or worse, us Y-chromosome types are still expected to take the initiative for the first one.
Amy: "I hear a lot of intelligent men whining about this. It's not fair. You're right. Get over it. If you expect to get anywhere, you're just going to have to deal with it. Even a lot of us liberated types are absolutely hard wired that the boy should make the first move. So cope with the fact that life isn't always fair and plan the first date."
Movie and dinner is a classic format that still works well; the movie will give you something to talk about, and the tendency to associate food-sharing with intimacy is wired right into our genes. But the kind of woman a hacker ought to be dating will be more impressed by the tastefulness with which you deploy your money than the amount you spend, so forget those ritzy places where the waiters wear tuxes and the bill is not much smaller than your typical car payment. Pick a movie with some idea content, and some funky interesting ethnic restaurant.
Cathy: Selecting a movie can be a challenge, though. If she wants to see The Bridges of Madison County and you want to see The Matrix, forcing the issue is likely to start the two of you off on the wrong foot. It's better for the two of you to talk it over and choose the movie in advance - and you should take mental notes on the kinds of movies she suggests during the negotiation process.
Amy "To drink or not to drink? If you're going to order drinks on your date, order the good stuff. Order a nice microbrew over Bud, Stoly over Absolut, select a nice wine over the house choice. (And if you don't know how to order wine, either let her, or order something else.) It's better to just order a coke than imbibe or ask your date to imbibe cheap booze. If the activities are going to be taking place at your home, be sure to have a selection of both quality alcohol as well as non-alcoholic beverages. Your date may not drink at all and having some sodas and juice in the fridge makes you look thoughtful and responsible. Next, don't drink too much. It's a good idea to keep it to 2 or 3 drinks (depending on your tolerance). If a drink or two goes well with the meal and helps you loosen up those nerves, it's a good thing. If you make yourself look like a drunken idiot, your date is just going to get worse. This is not the time to get sloshed."
Think about more unusual and interesting things to do. One of the most successful dates I ever had started with dinner at a Mongolian-barbecue place and followed with a visit to a gun range, where I taught the lady basic pistol technique. She was grinning ear-to-ear when we left, and the rest of the evening went extremely well for both of us.
If you have a hobby she's intrigued by, try theming a date around that. Do you ride horses? Climb rocks? Sail boats? Any skill with a basic level rapidly accessible to a novice will do -- she'll have a much better time if she gets some early victories. Outdoor physical-skill stuff is great because sunlight and adrenaline makes humans of both sexes horny -- and women are wired to find competence very sexy in a man (see How To Be Sexy). But don't make the mistake of assuming that stuff like videogames or fighter sims is going to do it -- they're not interactive enough.
Cathy: They are not interactive enough because they require each participant to engage in single-minded concentration on something that does not directly involve the other participant. You're here to do something different than that, remember?
Amy: "If you do take her out for competitive activities, and she kicks your ass, get over it. I can't stand men whose ego can't take it if I'm better at something that's considered a male arena. If you want to date a modern woman, be prepared for this."
Warning...warning...warning! Beware the more general dangers of excessive geekout. Even if your date is a techie, the odds are much against her wanting to talk about computers or technical subjects all evening. If she brings them up, fine, but you should resist the urge to divagate at length about your latest hack. Women, even techie women, have this odd idea that there's a life outside of computers and that interesting men ought to know something about it. They do not consider monomaniacal focus on technical subjects to be sexy. Trust me on this.
Listening well is sexy. One thing hackers are good at is maintaining complex state in their heads, and you can use this to devastating effect. If she mentions liking a book you've never read, hunt up a copy, read it and drop it casually into a later conversation. When you do this, you're letting her know you pay attention and value her opinion enough to act on it. You're making it clear you think about her when she's not there. You will score serious points for this.
Amy "But over-doing this can be creepy, so be careful."
The key point is for the two of you to have fun. The date is going well when you forget you're on a date and simply have a good time together. This is as much a matter of attitude as what you actually do. If you're relaxed and happy (and not worrying about how "the date" is going, or whether you're going to get lucky, or whatever) that will communicate itself.
It is therefore unfortunate that the ease of being relaxed varies inversely with the attractiveness of your date. It can be pretty difficult if you find her so sexy that your gonads are in an uproar a lot of the time. Might be she's having the same problem! This kind of mutual missile-lock happens more often than you think, for a couple of reasons. One is that a lot of human responses about what we find attractive seem to be biologically keyed to stuff like having the right amount of genotypic difference from the potential partner to produce a robust immune system in your offspring -- and that measure will be symmetric between the two of you. Another is that your scent, your body language, and even the timbre of your voice all change subtly when you're aroused; women detect and respond to this below conscious level and, if they're in a receptive mood, get aroused themselves.
So if it's hard to relax because she turns you on a lot, the odds are somewhat better than average that you're ringing her chimes too. Women are socialized to play that much cooler than you are, and under civilized rules you're pretty much required to play the game at her speed. There's not much else to say but "suck it up"; this is one of the hazards of being male, and we've all been there. Your only good option is do the usual physical-flirtation protocols and hope she escalates.
I described some of the flirtation protocols in The Art Of The Pickup; the stuff about how to touch a woman intimately is especially relevant on a date. Again, letting your sexual interest show at a controlled, consistent level is your best bid for a response. If she relaxes into your touch, that's encouragement. If she touches you back, that's escalation. But take your time and pay attention; a bit of sexual tension will arouse her too, after all, but rushing things is liable to spook her.
The stuff about manners is important, too. Courtesy pays. This doesn't mean you need to be stiff or formal, but almost all women appreciate little gallantries like opening doors for her.
Do offer to pick up the check for dinner or whatever, but don't insist if it's clear she wants to pay her own way; for many women (especially women with jobs and careers) not being indebted to a man is an important assertion of equality. In fact, under today's conditions, a financially independent woman allowing you to pay for dinner is a bit of a `go' hint -- if she doesn't mind owing you a little now, it may be because she's thinking about being good to you later.
Amy: "I generally consider it polite to insist on paying if you were the one to invite the other party. When you get to know eachother, it's cool to go dutch or switch off. This isn't a matter of sexism. If I invite someone to dinner, I expect to catch the check, and vice versa."
For similar reasons, flowers and candy and other expensive courtship tokens are nowadays kind of iffy before you've settled the sexual level of the relationship -- women don't as a rule want to feel like they can be bought with money or money surrogates. After you've been intimate is the good time for gifts, so they read as tokens of appreciation rather than bribes. But there is one exception to this. Clever, inexpensive gifts that express your personality (that don't put her under a feeling of obligation, but send a message) are always appropriate. Especially gifts you made with your own hands or mind.
Amy "My best friend has a suitor who is really interested. She wan't sure if she was interested. They both hail from Philadelphia but she lives in CA now. She recently mentioned to him how much she misses some certain type of cannoli. The next time he was in Philly, he fed-exed her a huge box of these cannolis. This turned her into a quivery pile of mush! It was much more thoughtful than the standard flowers. It was also not a `pushy' present. It showed he was paying attention to her and also that he was willing to respect her wishes to take things slowly. A+++ for him!"
An important bit of dating protocol, and one that has changed little since the automobile transformed our mating habits early in the 20th, is the end of the evening out. When you say "Where to now?", if she says "Your place", you can safely assume you aren't going to have to settle for a kiss goodnight. "My place" is more ambiguous, because even today most women will be unwilling to come right out and proposition you. Could be you struck out, or it could be she wants to make love with you in her own bed. You won't know until you take her home, at which she'll either invite you in or not. If she doesn't, game over and better luck next date. If she does invite you in, it is good form at that point to make a gentlemanly but definite pass at her -- go for the serious smooch and see what happens. Whether she treats it as the kiss goodnight or escalates will determine the course of the rest of the evening.
Right. So now let's assume that the date has gone well. So well, in fact, that the two of you are now in the process of removing your clothes and preparing to do the horizontal bop. What next? We'll cover that in the next essay, On Being Good In Bed.
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