People these days put some much emphasis on dating. Dating really isn’t as big of a deal as we make it out to be. However, because we make it such a big deal, it ends up going horribly wrong most of the time.

And now, the idea of a first date leaves such a bad taste in our mouths. But it doesn’t have to be that way. Imagine if you could go on a first date with someone and know it was going to be fun.

There is a way to make dating an event to look forward to. In order to make that happen, you will have to follow some crucial, but simple steps.

Pick something fun to do

How do most men ask women on a date?

“I would love to take you to dinner sometime”

Nothing wrong with offering to take her to dinner, but when it comes down to the actual date you should do something else. Dinner is so the last decade.

The best way to figure out what to do is by thinking about what cool things you have in your area and taking advantage of them.

For example, I live in downtown San Diego and there is an area called Seaport Village by my place. It’s a pleasant 10 minute walk to get there.

Once you arrive they have a bunch of little shops to peruse through. They even have a hot sauce store that sells some of the strongest hot sauces in the country (I sampled one with a friend and cried literally for 5 minutes straight.. ice cream on my tongue didn’t help.)

Seaport Village also happens to be right next to the water. So you can sit on the grass and enjoy the wake from the boats crashing onto the rocks nearby.

Doesn’t that sound way cooler than going to stupid dinner? It is way cooler.

Leverage your knowledge and connections

Do you have a friend who bartends at a local spot? Or maybe a buddy who works at an amusement park?

It’s always nice to know someone at the place you take a girl to. It makes you look good plus you probably get a deal.

If you absolutely have to take a girl to a restaurant because you’re both weak and feeble as a result of forgetting to eat for days, then FINE. But at least take her to a place you know someone.

I have a friend who’s the General Manager at a good Italian restaurant. I’ve taken a few girls on dates here and I’m not going to lie this guy has definitely helped me get laid.

He makes me look like the man. Period.

He greets me like I rescued him from a near death experience. He gives me the red carpet treatment and girls love it.

“Sometimes you wanna go where everybody knows your name.”

Really though, it helps.

Do’s and Don’ts for the first date


 1.    Be too serious. Yes you discuss serious topics, but dating is about getting to know each other and appreciating each other’s company. In other words, don’t make it like a job interview.

2.    Talk about past relationships. This is a mistake people make often and a lot of the time they feel it’s ok to talk about because the other person asked them. If you are going to answer the question “Why didn’t you and your ex work out?” try keeping it under two sentences.  Like “She is a great girl, but we weren’t a good fit for each other.” Never bad mouth your ex it makes you look bitter.

3.    Pretend to be someone you’re not. I shouldn’t have to explain myself here. Be honest about who you are and what you do. If you lie, she’s either going to find out that day or another day and then you’ll look pathetic, but eventually you’ll have to deal with it. Plus do you really want to date someone who’s dating the person you pretended to be? I wouldn’t want to.

4.    Drink too much. You may think you’re funnier, more charming, and more confident, but you’re probably not. There’s no need to hide behind a cocktail glass. On the 3rd or 4th date getting drunk is more acceptable if you’re into that.

5.    Be late. You don’t want to start off by annoying your date. Punctuality says a lot about a person like whether they respect your time or not. And there is no such thing as showing up “fashionably late” for a date. That’s only for parties.

6.    Not eat. This mostly applies to women. One of my biggest pet peeves is taking a girl to a place with great food only to see her order a piece of lettuce. I think they call it “salad.” If you think not ordering an entrée makes you look skinnier, prettier, or mysterious it doesn’t. Men like a girl who can eat a real meal. I’m not saying you should order 4 cheeseburgers, but at least get something filling.

7.    Talk about money or being rich. Yes some girls are attracted to a guy with money. In fact most people in general are attracted to money. But, something even more attractive than money is ambition. It’s better to talk about what you are focusing on and goals you have set for yourself, rather than listing out your accomplishments.

8.    Wait till the doorstep to kiss. You would think this only happens in movies but it doesn’t. Even Will Smith in the movie “Hitch” says if she shakes her house keys at the front door, she’s ready to be kissed. And that’s why we call it Hollywood. Waiting until you are parting ways to kiss is like working a business deal with someone and trying to close them as they are walking out the door. It’s too rough around the edges. You should always go for the kiss at some time in the middle of the date.


1.    Put your phone away. Technology is great and all but holy shit don’t let it consume your life. When our parents were our age do you think they busted their phone out to check out their latest Facebook notification? No. They did something that is slowly fading in today’s society. It’s called conversation. Talk to each other, get to know each other, and don’t bring your cell phone out unless it’s an absolute emergency.

2.    Listen. Sounds easy right? Don’t ask me why but so many people have a hard time with this. Everyone appreciates a good listener. People like talking about themselves but only to someone who is actually paying attention. Learn about the person and ask more in depth questions than “What do you do?” For example I like to ask girls to explain what they do to me as if I was a 2nd grader. Reason being is often times I’ll ask someone what they do and they say “Business Development and Programming Analyst.” Cool. What the heck does that mean? So take the time to get to know people and understand them better.

3.    Show positive body language. Guys lean back, don’t slouch, and make solid eye contact. Girls if you are interested lean towards him when he talks, make eye contact, and smile. If you really like him, you’ll do this naturally.

4.    Sit next to each other. One thing I can’t stand about first dates is the awkwardness. When you’re in a restaurant and you see two people on a date, it’s so easy to identify if it’s a first date. They sit far apart, ask a lot of general questions, talk about surface level fluffy bullshit. You should change that. Make it feel like it’s your 10th date and here’s how. First of all you should sit next to each other rather than across. Second, you should have light touching during conversation. And if it’s going really well, you can feed each other like this little kitty below. Maybe even make airplane noises while you do it.

5.    Discuss what’s important to you. Talk about your values, morals, and how you see things. Always express your opinion and don’t just agree with the other person for the sake of getting along. This is a good time to bring up your fantasies if you have the confidence 🙂


The awesome thing about dating is there are no rules. Rules are set by society’s expectation of what people should do. Fortunately you aren’t breaking any laws by having an outside the box date.

I once took a girl on a first date for a walk and then to the grocery store to shop for my refrigerator. Believe it or not we had a great time. We ended up having a 2nd, 3rd, and several more dates after.

When planning and going on a date there are only two simple things to keep in mind. It’s about getting to know each other and having fun with it.