A Bro’s Guide to the First Date

by 5 years ago


If we could, bros would avoid first dates like the bubonic plague.

The initial ass-out hug, the decision to do dinner or a movie or try something more “original,” and, of course, the internal debate about whether to go in for a kiss at the end — it’s all pretty awful stuff, I’m going to try and sugar coat it.

Unfortunately, unless you’ve been dating the same girl since freshman year of high school, a first date is a standard social requirement that you must get used if you’re planning on living the bachelor lifestyle until your early 30s.

Sure, they’re uncomfortable at times — the awkward getting to know somebody always is, but at the end of the day a first date does have value in the larger scheme of things. They teach you how to communicate effectively, how to present yourself in a favorable light, and how to approach an unknown situation with reasonable expectations (sorry bro, she’s probably not going to come home with you on date one).

These are all important skills to have in life, not just dating.

I’ve always been of the opinion that talking to girls in general is like conducting a job interview — you’re taking resumes to fill a certain position (girlfriend) and you’ve got a very specific list of qualifications/experiences/characteristics that you’re looking to be fulfilled.

The only difference between a job interview and a first date is time — if a boss doesn’t like you’re resume, he or she will simply skip over you and move on to someone else.

With dating, there isn’t such a luxury and that’s what makes first dates appear so painful on the surface: there isn’t an exact period of time it should last. The date could be as brief as 30 to 45 minutes or it could end up lasting the entire night night; it’s all pretty much circumstantial and entirely out of your control.

Perhaps that’s why first dates are such a burden on the male psyche. Instead of being in charge and knowing what direction you’re heading in, we’re left floating into this undefined abyss with several dozen possible outcomes — sometimes it’ll be good, sometimes it’ll be bad and most of the time it’ll fall somewhere in the between, meaning you got along with her but you don’t know if she’d go out with you again.

However, first dates don’t have to be these daunting tasks that leave you feeling powerless.

Here’s a guide of what you’ll need to get through the date and help you move forward towards round two (depending of course if she qualifies for a second round interview):


I won’t spend a lot of time talking about this because I’m sure you’ve read plenty of guy-related columns about having self-assurance.

With that said, confidence is the most vital weapon you can carry with you in your arsenal on a first date but it can also be damaging if you come across as too cocky. You may be sitting there asking, what’s the perfect balance? And that’s a legitimate question.

It may seem like a bit of a childish example, but whenever I think of a fictional character that has the right amount of confidence without coming across as a mega douche, I always think of Austin Powers. He’s doesn’t suffer from excessive hubris, yet he carries himself like somebody who knows how a situation will play out and at the end of the day, he’ll be OK. That is his mojo and what attracts women to him (it’s certainly not his teeth).

If you approach a first date knowing that life will continue after it — regardless of whether it’s a good or bad experience, then you’re in the right state of mind and she’ll sense that right when you sit down. From the minute the date starts, you want to appear to know what’s going to happen next even though you might not.


Without question, the second most important skill you need to develop if you’re preparing for a first date. Women love a guy who can act on impulse, think outside of the box on his toes and create fun out of thin air. She’ll think you’re a magician if you pick her up and take her for a walk in the city, rather than just go to dinner.

It may seem difficult, but this is actually really easy if you take the time to brainstorm some good ideas. In case you lack any sort of creativity, here are some ideas for you:

  • Anything with physical activity — bowling, golfing, cycling, ice-skating, hiking, etc. (Caution: the girl may not want to break out in a full sweat in front of you on date No. 1, so you may want to ask her ahead of time or wait to do any of these for the second date).
  • A live event — concert, theater, comedy show, sporting game.
  • Something out of both of your comfort zones — cooking class, exotic dancing, rare cuisine (have you ever eaten shark?), hot air balloon ride, karaoke, etc.

I hate to throw this idea out there because it’s going to sound totally unmanly, but going shopping with her is something that’s really worked well for me over the years. If I were to guess why — and I really don’t have the answer here, it’s because people watching provides for a naturally fun conversation and trying out new things (clothes, hats, chairs) allows you to use material objects as part of your comedic collection to impress her.

Whatever you decide, make sure you’re somewhere where you can have a conversation and get to know each other. This is a perfect transition to my next point…


It sounds obvious but a lot of guys are disorganized messes who think that just showing up on a date will win the girl over. She’s already said yes so you’re in the clear, right?


Like playing sports, you must prepare ahead of time and put in some work before the game if you want to succeed on the field.

Some tips: know where you’re meeting and have directions; bring enough cash out for anything (parking included); know her food preferences if you’re going to dinner; read up on where you’re going, whether it’s a restaurant or a beach.


I put a lot of emphasis in this one because it’s an area of my own game that I constantly have to acknowledge and improve upon. Eye contact is essential in any conversation, but on a first date it could really prove to be the difference between going home empty handed and down on yourself and ending up in her bed the next morning grinning from ear to ear.

Equally important is physical contact, like touching her arm when you’re talking and flirting with her throughout the course of the date. The more you can do this; the better off you will be in the long term. And if she doesn’t like it or moves away from your effort to reach out and make contact, then you know she’s not the one for you and you can relax and wait for the clock to run out.

Take it from someone who guarantees he’s blown at least 10 situations with girls because he failed to engage physically; you MUST make contact with her on date one. If you don’t, you mine as well get ready for the next interview.


I bet you didn’t expect to see this word anywhere near this article. And no, I don’t mean heaving up you’re undigested dinner on her new dress.

As I’m sure your parents or somebody else has told you, the key to any good relationship — new or old — is listening. On a first date, you obviously must listen to what she says but that’s simply not enough to get the job done. You have to be able to pay attention at all times, but, most importantly, you have to show that you’ve been paying attention. This means spewing facts — regurgitation in action! — about the stuff she’s already said, like the time she went to Florida in the 10th grade.

If you can make a connection anywhere, then that’s the real sweet spot.

Note: Don’t be afraid to be wrong in your efforts to show her you’ve been listening. If it was actually Georgia and not Florida in her story, and you get it wrong, it doesn’t matter. Trust me, the effort is what counts and that’s what she’ll remember about you when you’ve parted ways.


When the spotlight is turned on you in the conversation, be upfront and honest. Making up shit about your life is only going to lessen your chances and will result in embarrassment eventually. The only details you can afford to fudge are habitual things like whether or not you smoke weed (the answer, for those of you who haven’t been here before, is always no).

One additional piece of advice while we’re here: always try to reverse the dialogue back to her. Girls like to talk about themselves and the less you say about yourself, then the more mysterious you’ll appear to be, which should be one of your goals on the first date.

Remember: she’s applying for the job, not vice versa. You don’t want to give away too much information right off the bat. There’ll be plenty of time for that later on.

No phone

This one’s pretty self explanatory but you’d be surprised how bros can’t stay off their phones for an hour while going out on a date. Even if she excuses herself to go the bathroom, don’t go into your pocket to try and text your boy about how the date is going.

There’s absolutely nothing that pressing to warrant the use of a cell phone; unless of course, she’s having an allergic reaction.

Exit strategy

How many times have we seen a coach blow a call in the fourth quarter of a big game? Unfortunately, this happens to bros on first dates more often than not. After managing the situation well for the first three quarters, you somehow find a way to blow it down the final stretch — you let her split the bill at dinner (a big no-no, boys), you tried to kiss her during the climax of the movie, you stepped on her toes while walking back to the car, etc.

How to handle your exit strategy is no different then the way you handle the entrance to the first date. You have to be relaxed, prepared and armed with confidence (a smile doesn’t hurt). You’re body language must say “I had a great time tonight and I’m feeling awesome about where this is going” without actually expressing that in words. If you’ve mastered this appearance, then I don’t see why you shouldn’t go in for the kiss. Even if she turns it down, she’ll understand that you’re interested in her and tell you how to proceed next if she’s mutually interested. If it’s not reciprocated, then you two will go your separate ways and you will return to square one with your dick in your hand and a bottle of body lotion in the other.

Of course, none of this matters if she’s a total bore and you’re rejecting her application for the job. If you’re going to bring in some other candidates to interview for the position, then tell her as much and carry on. No need to lie about it and try to force something out of nothing.

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