Guide to First Dates.

1. Have a plan, but be ready to drop it.

A typical first date plan, one that I'd recommend, is eating and/or drinking things, doing something, and then meeting up with friends later. But the "ready to drop it" attitude is at least as important as the plan. If things are going well, you want this person to think you're spontaneous and fun, and if things aren't going well, you're going to want an escape hatch.

Escape hatches are a necessary part of first dates. For ladies, the escape hatch involves setting up a phone call from a friend who'll pretend to be in distress if things aren't going well. This phone call is a must. Think of it as being "for security reasons." If they actually use the friend call as an excuse to skip out, we dudes will either get the message and have our annoying little feelings hurt (no big loss), or we'll be oblivious and obnoxious about it. Either way, it'll have been a good call to ditch out.

If you're enjoying a date and you catch her hitting the "ignore" button on the friend call, then it's like a little boost to the proceedings, and the date can totally take a trip into Flirttown.

Dudes absolutely cannot set up a friend call. That is a chick move. Your escape hatch comes later, in the "meeting up with friends" phase. More on this later.

The plan will probably involve at least one "cornerstone" which you've already agreed is the purpose for the date. Like when you call you say, "hey there's this thing or eating place I want to try out, I was wondering if you'd want to go with me."

Don't be intimidated by this cornerstone plan. If things are going really well, you can even drop the cornerstone. Only if they're going really really well, though. Dropping a cornerstone has the potential to catapult you from "he's fun and spontaneous" to "he's crazy and I love him" status. And that's a powerful weapon, that catapult. It can backfire. Use it with caution.

2. Getting ready.

I'm a believer in the whole "wear whatever you put on when you woke up that day" philosophy. If you've got a job that makes you wear a suit for some reason, and that makes you uncomfortable for your first date with somebody, then change. Jobs. (Self high-five).

Of course there can be a certain amount of requisite primping and accessorizing and such, but the major "what am I going to wear?" debate should happen in the morning when you wake up, not fifteen minutes before you're meeting up with somebody. That way you're comfortable and confident when you meet up with the person, and you're presenting a reasonably accurate representation of what you wear.

If you're the type of asshead who wears a ridiculous fancy shirt everyday, then by all means wear a ridiculous fancy shirt. You have to be accountable for your appearance, and a ridiculous fancy shirt sends the "I'm an asshead" signal right away. Great for you if you're an asshead. Don't be surprised if your date's friend ends up calling from the hospital after like an hour though.

If she is wearing a ton of makeup, you know she’s overdoing things, and that’s a good red flag to look out for. Tons of makeup are the girl equivalent of ridiculous fancy shirts.

In terms of attitude, you want to be comfortable, confident, and relaxed. Do whatever you need to do to get there. If that's pulling a "Something About Mary," then more power to you. I'd recommend wailing on a drum set or something, because that drains you of aggression but keeps you mentally sharp on the “still need to jizz” front.

3. Meeting up to eat and/or drink.

Ironclad rule: dudes pay. Sorry. Call me old fashioned, but if you can't afford to pay for a grilled chicken breast sandwich and a couple of Miller Lites, then you should be working instead of dating. Check the “jobs” section of Craigslist. Don't make a big fuss about it, just anticipate the bill and get there before she does. If she puts up a bit of a fuss, then you've got a keeper, first of all, and second of all, you can do this little game where you'll be like "I'll let you pay for me later," and then at the next thing you anticipate again and she puts up even more of a fake fuss. It's like built-in flirting.

You can be a little less flirty with it if things aren't going well, but you still have to pay. Also, you should let her pay for popcorn (or popcorn equivalent). That's the girl's job on the first date to show that she can pay too, just so you don't get the wrong idea about how she'll be a kept woman on your 25 thousand big ones a year. Like I said, these things are like built-in flirting.

Pick a place to eat/drink that isn't too crappy or too intimidating. You don't want to take your first date to ten cent wing night at Dusty's, unless Dusty's has like a really nice beergarten. You might feel perfectly at home in Dusty's, but if the girl really likes you, you don't want her to see the whole "Dusty's again?!" argument coming from three months away. You'll want to go to someplace that you've been to like once or twice.

Also, really nice restaurants are kind of a bad idea for a first date. This might be my own personal philosophy here, but really nice restaurants up the ante for overly proper manners and "which fork should I be using?" self-consciousness, which already have the potential to be going at full blaze due to the whole "first date" thing, so you're looking at a possible perfect storm of awkward if you take a first date to a really nice restaurant. Plus, let's face it, it's a lot of cashola and you don't know if she's worth it quite yet.

If things go well at Dusty's really nice beergarten, then later when you're walking down the street and you pass Chez Alfredo, you can mention how you've never eaten there but you'd love to as a nod to the "I also like to eat at nice restaurants" thing. You'll want to drop at least a hint in that direction.

During the eating/drinking phase, confine yourself to two beers. It's the perfect number. Nurse the second one slowly.

During conversation, listen and ask questions. When you speak, try to speak more about things you like than about things you don't like. Encourage her to do the same. This will lead you to opportunities to be spontaneous later. Avoid swapping stories or any other conversational one-upsmanship.

4. Spontaneous thing between eating/drinking and doing a thing.

Here's where your skills of detection come in handy. If things are going well, you can use some of that information you learned from the conversation about things you both like to do something "spontaneous."

My all time favorite "spontaneous" move is to go to a bookstore or record store and buy books or records for each other. Every worthwhile human being on the face of the planet likes books and/or music. So you buy each other one of your favorites that the other person hasn't gotten to.

It works on so many levels it's ridiculous. First of all, you get a gift out of the deal. So that's always good. Second, you've been "spontaneous." Third, the person you're with gets to see you be passionate about something, which is a big time bonus for girls because it sets off the part of their brains where they're like "he could be that passionate about me one day" and their hearts go squish. Fourth, it's got a really fun Easter egg hunt vibe to it. Fifth, they can’t actually listen to it or read it until the date is over, so there’s not much backfire potential unless you’re dumb enough to get her a Tool CD after she just told you how she’s “not into heavy metal.” You’re not trying to convince her that Tool “fucking rocks,” here. Guy. Get her a thing that girls like but you also like.

Now that I've given you the goods on the all time best spontaneous activity and it's written down on this guide that everybody's going to read and follow to the point that it's no longer spontaneous and just something that's a part of every date, I'll also mention how important it is to actually be spontaneous in a really spontaneous way. Like if you have a conversation about boat rides and then when you're on your way between the eating and drinking place and the thingdoing place there's a guy selling boat rides, then go on a boat ride. Duh.

The important thing is even if things don't work out long term with whoever you're dating, if you're spontaneous you'll have more ideas of things you can do around the city and therefore you'll be more likely to be successfully spontaneous on subsequent dates. You're setting up a "culture of spontaneity" for yourself, which is something I'd write about more if I was some kind of Oprah-sponsored corporate bullshit artist. Point is you want your own spontaneous staples, like the gift exchange thing.

5. Doing a thing.

This is probably your cornerstone event of the date. Be smart choosing it. You’ve got a whole world of options. There’s your basic “Hey, have you seen ‘Current Hotshit Indie/Date Film Release’ yet?” (boring), your more advanced, “Hey, they’re showing Ferris Bueller at the Music Box, wanna go?” (getting there), and then there’s “Hey, I’ve got some friends that do this really fun slideshow thing where they talk about, like, the history of ice cream or something but it’s really funny and weirdly inspiring and there’s beer and all kinds of librarians and grad students in courderoys, you want in?” (bingo).

If you really like somebody enough to ask them out, then you should have an interesting hook like that. So that even if they’re not sure about you, you’ve at the very least come up with a plan that they’re interested in enough to go with anybody. And your plan is a reflection of you. So make it interesting and weird and fun. And the more sort of weird it is, the more you have an opportunity to use the “he’s crazy and I love him” catapult.

There are all kinds of great things like this every week if you check your local urban free weekly “look at all the cool shit we know” bragazine. Like a Pat Benetar cover band or a lecture about bugs with real live bugs there or something. You might want to have two or three of these plans lined up during your initial call in case your date is really afraid of bugs or can’t do anything on Wednesday.

And remember, if there’s an opportunity to do something that you think there’s a good chance your date will enjoy more than the cornerstone activity, take it. You can find out about this through the magic of asking. Your date will be somewhat indecisive because she’s being polite and she doesn’t want you to miss out on this big thing you have planned if you’re really into it, but within that indecision there will be hints about which way she’s leaning. Pick up on those hints and don’t give her any shit for being indecisive. Ever. Indecision is every woman’s birthright as a mysterious and beautiful creature.

Indecision bonus guide: women don’t respond well to direct questioning. They want you to come up with the plan. Especially if they like you. If you’ve got options, it’s your job to pick the one you think they’d like the best. Or if you want the date to end, you can boldly choose the option you think she’d hate. Also, when it seems like your date is asking you a question, she’s actually telling you something. Like if you walk past a baby toy store and she asks, “Hey, want to stop in here?” You say yes and you stop in there. She just told you she wants to stop in there. It just sounds like an indecisive question to your dumb boy ears.

During the thingdoing you’re allowed two more beers. Tops.

6. Meeting up with friends later.

It’s a little weird and counterintuitive to set this up beforehand because it’s like you have to plan two dates at the same time, but it’s a good move for a number of reasons. And it shouldn’t be all that hard to figure out. You probably have at least one friend who’ll be out on any given night. Send a multi-text from the bathroom during thingdoing. It’s worth setting up.

For one, it’s the dude’s escape hatch. If you’re a dude enough to call somebody and ask them out, then you’re going to at the very least pay for their food/drinks and take them to a thing. That’s your minimum obligation. Always mention the “meetup with friends later” at the beginning of the proceedings, so you can use it as an excuse to go your separate ways if things are pretty brutal.

If things aren’t brutal in the slightest, or they’re right on the fence, then it’s a good to put a “me and my friends” context on things. If you’re super into whoever it is, you can be like “hey, I’m a package deal and these are my wonderful friends.” If you’re on the fence you can see which way works out the best by seeing if they get along with your friends.

I should mention that by friends I mean “a mixed group of guys and girls who are witty and fun.” You don’t want to bring your date into hour three of dude’s night out or into some structured mass of This American Lifers who are quietly pontificating about the role of corruption in the Mayor’s office over wine, cheese, and Boggle. Those can come later. For the first date, you want a nice mix, and you want to hit it around midnight, right as everybody’s just getting loose but before anybody’s too wasted.

It has the potential to work out great. Girls always love to meet other girls that you’re friends with, because of the new bestie potential and to make sure you have a trustable voucher for being a good guy. Girl wingmen operate on the “help each other say no” principle, so if you’ve got a girl who’s not telling your date to say no to you, it’s great. If you can somehow arrange a meetup with a group that includes an ex that you’re still really good friends with, but who is clearly out of the picture, then that’s the best possible voucher you can get. But of course that doesn’t exist.

And while this checking up and girl talk is happening, you get to pal around with some of your dude friends, who will do their best to make you look great because dude wingmen operate on the “help each other get laid” rule. It also works because your date is seeing you in your natural setting. And there’s booze.

The best thing about meeting up with friends later is that your date ends in the context of hitting on somebody in a bar. But you’ve already put in all this great work with the whole date thing, so it’s WAY easier than usual. If she’ll go with you to a bar full of your friends, she likes you. You’re in the clear. Try to keep a level head.

Now one of two things happen. You either end up in the same cab or you don’t.

7. Either ending up in the same cab or not.

This is tricky territory. Cabs are the new front door. Unless you’re within walking distance from her house and her front door is the new front door. In which case, replace “same cab” with “inside her apartment.”

Rule number one: don’t be pushy. I mean, you wouldn’t have gone through all this effort of going on a date if all you were looking for out of it was to simply get laid, right? Right? I mean, if all you want to do is get laid, you can do that pretty easily without spending all this time and money on somebody you totally have a crush on. You can wait. You’re an adult.

What you want to do is project that. Try to subtly send that signal. But you also want to cover that with a glaze of “I’m wildly attracted to you” so she doesn’t get discouraged. The idea is to put her in a position where she’s saying yes instead of no.

Let me explain that so it sounds less rapey and weird. If you’re pretty sure there’s a no in store for you, don’t ask for whatever that is. This is all noverbal communication stuff, and highly experimental and subtle. But it’s basically “I’ll wait as long as I need to for a yes rather than making you uncomfortable.” It’s all word tricks. If there’s a lull, you can be like, “wow, it’s one o’clock; time just flew,” without any sort of judgment to it and you’ll get a reading on things with way less potential for embarrassment of both parties than “Hey, you want to get out of here?” You’ll want to take a reading or two like this before you make any push for a same cab scenario.

But if you're getting the right signals, the direct approach is a good idea. Honesty with self-awareness and without committing too strongly is what you're shooting for with the "direct approach." Something to the tune of, "Hey, I think you're great and I've had a wonderful time today, and I don't want to make you uncomfortable, so I'll just say 'I don't want this to end here' and we'll just treat that like a nice thing I said instead of me being pushy." Something like that. Stay sober enough to pull this off. But get drunk enough to try it.

If you end up in the same cab, then don’t make her wait. Kiss her in the cab. Cab kisses are kind of great.

If you end up in separate cabs or you come face to face with the “have to wake up tomorrow” white lie – a fine white lie that doesn’t necessarily mean anything bad for your long-term chances – then do everything within your power to avoid saying the phrase “I’ll call you.”

Like 90% of the Mars/Venus dating issues that there are in the world come from this phrase and the misuse of it. The whole “why don’t they call when they say they’ll call?” thing has become so absurdly overblown that nobody should ever say they’re going to call ever again. Even if they’re like “call me, ok?” You should give them a Bill Murray-esque joke like “we’ll see” or “if you’re lucky.” If they don’t laugh and/or they insist that you tell them you’re going to call them, then that’s red flag number one (if you haven’t got any other ones for the entire date).

If you’re still pretty into them, text them in like five minutes with a “that was fun” so they get it in the cab and they’re all smiles when they get home.

And then they can do that thing like in the movies where they close their front door, then turn around and lean their back against it and bite their lip and roll their eyes and slide down until they’re sitting on the floor.

8. Conclusion.

And the ideal first date ends like that: with two people who are really excited about getting to know each other. If one person or the other isn’t excited, then it’s time to cut and run right there during the first date because it’s not going to get any easier later. If you’re not biting your lip and rolling your eyes and sliding to the floor, then forget it. You’re only going to get less excited. Cut and run. That’s your responsibility under the “we’re all adults here” rule. You’ve built a plan with escape hatches. Use them. It’s for the best. But if you’re both excited, then congrats on either being totally in love or successfully fooling each other. You’re past the first date.