It’s ironic to say it about a column that’s literally about how to do first dates correctly, but most people get way too worried about themSo, before we start, say this mantra with me: This is going to be a fun night. That’s your goal. That’s what you should aim for in any first date scenario, in the same way that you would plan a fun night out (or in) with a friend.

With the cultural weight that the first date has—that this is the beginning of something special—many guys (heck, a lot of girls, too) go in forcing said concept, that this is going to be a magical night that must be the most special thing, the most perfect thing, the most immaculate day of said woman’s life so that you two will fall in love.

Alternatively, the guy goes in there asking, “How can I get in this girl’s pants?” If you want a guide for that, I don’t know what you’re reading this for. I’m not your professional one-night stand machine; take a hike. But if you’re looking for some time-tested, no-nonsense tips about prepping for a great first date, read on.

Your goal is to have a worst-case scenario of “that was a good meal/drink/etc.” Unless she’s just that bad.

Establish That the Date Is Both a Date and One You Can Have Fun On
As I’ve said before, you really should be making sure that this is an actual date you’re going on, if you didn’t ask her out on an online dating site. This is as simple as asking— and no, this does not mean saying “it’s a date” at the end of the conversation—“Hey, can I ask you out on a date?” or something along those lines.

Once you’ve established that, you also want to make sure you want to spend time with this person for more than 20 minutes before wanting to jam a cocktail skewer into your brain. It took me a great deal of time to work this out, and many, many dates, but this is as simple as having a few conversations with the girl beforehand before the date and following your gut. If you’re having a conversation that’s only interesting because you are imagining at some point you could touch one, or potentially two, boobs, then you’re probably not going to have a great time. If the conversation is mostly “K,” or “lol” or generally forced, and it’s not been established that she doesn’t like texting (yes, this does happen), I’d probably consider some degree of caution. Perhaps you want to try and get on the phone with her or Skype (do not take your shirt off or your penis out in said Skype conversation unless explicitly asked to).

Planning the Date (Or Not)
In the mind map of most men, there are two paths I see most commonly for a date:

1)   I’ll take her out for a drink.

2)   I will create a vast romantic escapade that involves a walk through the park then flowers then jewels and a horse and a carriage and the carriage is made of gold and I have spent hours planning this.

Neither are exactly perfect, and the second option is worryingly common around guys I know that are just naturally afraid of dating. This is a totally valid emotion to feel, and one I’ll address more in detail later, but goodness, it’s a first date.

And yet the first option can sometimes be a toughy. Some girls don’t drink. Some girls don’t drink a lot. Some girls drink way more than you do. Some girls want certain drinks. It’s dicier than you’d imagine it is, and one that you have to play by ear.

Some General Purpose First Things to Do
-Get things like “I’m divorced” or “I’m an alcoholic” out the way in advance. Yeah it’ll ruin your chances of a date with someone but, guess what, learning this later will ruin a relationship.

-If you are going to a restaurant or a bar, get a reservation. I heartily recommend not going to somewhere that may have a wait. Unless you really hit it off just being around each other, waiting for a table is not a good look for you, bud.

-Don’t bring roses or a gift. Don’t make a mixtape.

 Don’t, my god, do anything outside. I know someone will disagree with me and say they met the love of their life doing this, but unless you live somewhere with some fantastic weather or you’re 99.99999 percent sure it’s going to be a glorious day, do not count on the weather.

-Always have a backup plan. Seriously it’s just common sense, man. Get another reservation. Cancel it once you walk in on OpenTable. Or, alternatively, have somewhere nearby that’s walkable and nice.

– If you go somewhere, at least go somewhere you can actually talk. Go somewhere you feel comfortable. I’d recommend no new places. I’d recommend not going too fancy unless you really, really love the place. Sort-of-fancy-so-you-can-look-good-but-not-so-fancy-you-require-a-suit is a good, ultra-hyphenated rule of thumb. If you live in the right area for it, that is. Your goal is to have a worst-case scenario of “that was a good meal/drink/etc.” Unless she’s just that bad. I doubt she will be.

-Pick up the god damn tab (if she lets you). Unless it was a completely bullshit, horrible date—the kind that you will remember the rest of your life and say, “Isn’t this hilariously bad?” that’s on you. So make sure you pick a place you can afford, too. There’re some girls who will insist on going 50/50. Say, “Come on, I don’t mind.” If she’s okay with it, pick it up, you’re a gentleman. If she’s insistent you split, it either means A) she didn’t have a good time, in which case, cool, you got half the meal paid for at least or B) she likes to go halves on first dates, in which case, cool, you got half the meal paid for. It’s fine to even say, “Hey, look, I’m not expecting anything,” if she seems nervous. Some girls, rightly, have got the notion in their heads that a guy who picks up the tab expects to go to Sexville, KY. Guys, paying for dinner doesn’t mean she owes you anything. Sorry!

Always remember: It could be worse!

How to Dress
Dress who you are: Whatever you wear you should be comfortable in, for starters. Don’t buy a bunch of new clothes for said date, especially if you’re wearing things like polos or button-downs for the first time.

Make sure your clothes fit you properly, which is a whole other column entirely. Even a man who’s got a bit of weight on him can look good as long as he wears the right-sized clothes and feels good in what he’s in. And don’t bust out a full custom suit and your nicest shoes and an expensive watch you borrowed from your buddy to impress her. She’ll see through it.

On my first date with my girlfriend I wore a custom pair of suit pants and some Ferragamos, because I felt comfortable and attractive in them. I wear this to work functions, and I feel confident in them. That’s why I did it. Not because I wanted her to think I was super cool or had money. I just checked and she didn’t even look at my shoes. (Editor’s note: Most girls do look at your shoes. And she probably would have noticed if Ed’s were terrible.)

Still, do make an effort: A girl may see through your façade if you’re faking a particular look, but, goodness, wear your good stuff. A clean shirt. For example, if it’s a casual thing, you can wear sneakers, but not if they’re falling apart and covered in dirt. Dress for the occasion: If you’re going to Dave & Busters, the nicest you’re gonna want to wear is a polo and jeans. If you’re going to a restaurant, perhaps wear some slacks and dress shoes and a button down, but heck, if a polo’s okay, wear a polo. This is very basic advice that guys miss. I’ve heard of guys taking girls to steakhouses in jorts. Guys, come on.

So now you know how to prep. Tune in next week for more on how to actually go on this date and not totally blow it.

Photo Credit: Twenty20/@christians2156

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