How to plan a first date in four easy steps

First, I am going to ask your forgiveness for using female pronouns almost exclusively for the object of your desire. Of course you could plan a date with a guy or any other gender, and these rules still apply. However, this post does center around traditional first-dates, which many of us modern 20-somethings may not have a taste for. Although, I must say, they have their place.

It is actually very simple when it comes down to it. I have broken it down into four easy steps for you. This formula is great for planning a first date with a new interest, or for finding something special to do with somebody you're already with when you want to treat him/her.

1. Find out when she is free

This is actually the hardest step of all. Clearly, the asking can be the hardest part for many reasons, not the least of which is making sure the person you're interested in knows it's a date. We all remember that episode of Friends when Rachel tries to ask a cute client on a date for the first time and he thinks that she is gifting him two tickets to a basketball game rather than asking him out. OOPS! (by the way, when I say "We all remember," I really mean "I can't be the only one who remembers this... right?")

So yeah, you have to find out when she is available, and she has to know that it is actually for a date, not some friend chillout time, not some big group outing, but a real date. Since this post is about planning the date, not asking people out, I do not have to give you advice on that. What a relief.

2. Find out what cool stuff is happening that day

If you live in a city like Chicago, there's always cool stuff going on, much of which is cheap or free and pretty darn interesting. Check out any kind of listings you can find. Here, the Chicago Reader or Time Out Chicago may be of service to you. There are free movies in the park every night, there are always comedy shows, there's always pretty cheap music to see, etc. You should never be at a loss for something to do, but try to pick something a little bit off the beaten path. Getting creative makes you look like a smarter and more thoughtful person, and bitches love the smart, thoughtful types. But seriously, when you pick something a little more creative, you have a unique shared experience with this person, rather than something run-of-the-mill that she will be quick to forget.

If you live in the country, go see a movie or something. I don't know what the hell else people do in the country. Bowling? Do they go bowling? I dunno. I'm not gonna hate on you for being uncreative if there are no creative choices available to you.

Here's an example of a really unique date I was asked on once. About two and a half years ago, in the dead of winter, a new acquaintance asked me to go swimming with him. We went out to dinner and snuck into the pool at a nearby hotel. It was super creative, and obviously I have yet to forget it.

3. Find a nice restaurant near your chosen activity

Finding nice restaurants is surprisingly easy. Checkout urbanspoon.com, one of the easiest ways to find out what restaurants are most popular in a given area. A lot of the restaurants have the menu included so you'll know what you're getting into price-wise. Don't feel pressured to take your date to the most expensive restaurant. Atmosphere is far more important than price, and any girl of real value will be just as able to fall for you over a $30 dinner as a $100 dinner. If you have never been to the restaurant, be sure to read plenty of reviews (yelp, anyone?) before deciding. If any reviews have the word "romantic" in them, you're golden.

When you decide on a restaurant, make a reservation, even if your date is on a weekday. They say "You can't hurry love," but pausing it because of insufficient planning cannot be good.

4. Figure out transportation and show up

Driving? Cabbing? Training? Whichever you choose, plan it out before the date. You don't want to get your directions all mixed up and be late for your reservation, do you? Then just comb your hair, wear some nice shoes and show up on time.

Here's an example of a recent date I went on that would have been perfect, except it was a friend date:

I met up with my good buddy George and we had dinner at a really great Asian restaurant that is kind of off-the-beaten-path. Afterwards, we headed over to the Goose Island brewpub in Wrigleyville and enjoyed a couple of beers. We ended the night with an improv show at iO, only steps away from Goose Island. All in all, it was a very enjoyable night, and it would probably make a pretty nice first date.

So clearly, this formula isn't rigid. If you go to a movie in the park and have the kind of time/talent to plan a picnic, that's fine. If you decide to go to a different place for drinks before dinner, just make sure to research it just as much as the restaurant. If you have a favorite place you would like to take your date for dessert, that would be adorable. The formula simply makes it very easy to plan the always important first date.

As I mentioned earlier, I hate traditional dates, but honestly, some girls really go for that shit, and it does have its place.