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The First Five Minutes of a Date


How to Start a Date with a Woman in a Way That Almost Guarantees a Good Time

I used to absolutely hate going on dates.

A few years back I was big into online dating and was literally going on three or four dates a week.  And I was miserable. I would find myself bored, anxious, intimidated and usually severely disappointed. And I rarely got laid.

I want to tell you the story about a realization I had that made me go from absolutely dreading going on dates to not only start enjoying them, but very often finding myself in bed with the woman by the time the night was over. I remember when I used to believe that a date was a “formal”, “sacred” encounter where you had to portray yourself as the perfect gentlemen. And your sole responsibility was to ‘not fuck it up’ – and to prove emphatically to the woman that you WERE NOT interested in sex.

Isn’t that what most of us were taught?

I mean doesn’t it make sense that women want a respectful, nice guy … who isn’t looking for a one night stand? You would think so. But when I really started to pay close attention, I started to notice:

1. The harder I tried to impress a woman on a date, the less likely I was to get a second date.

2. My “timidness” that I thought was putting a woman at ease was actually making her more nervous and LESS likely to open up to me.

3.  And the more formal and “gentlemanly” I made the date, the more we grew more bored with each other, and would quickly run out of things to say.

“Some guys just don’t learn”

Date with man and woman

Date with man and woman

You would think that after going nearly fifty dates over the span of a few months that I would have caught on that I was doing something wrong. But I was like a retarded person continually banging my head against a brick wall. Finally after a date in which ended with me faking diarrhea (seriously) to avoid paying for another meal with a woman who was clearly not going to sleep with me anytime soon, I decided that I needed to formulate a new game plan if I was going to continue going on so many dates.

Around this time I had begun reading some dating advice websites and read that “dinner dates are bad.” I was told I should be taking women for coffee or ice cream instead. My wallet liked this.

But changing the environment of the date had little impact on my success.  We were still two bored, nervous people, only now we were sipping coffee, instead of digging into pasta dishes. In fact, it was worse.  Because now we didn’t have the food to distract us from our boredom.

“The date that changed everything…”

I finally decided to cancel my membership and take a break for awhile. I had been talking to this cute Portuguese girl for a couple weeks and figured I would make her my last date before I called it quits. Our email exchanges were pretty mundane and boring, so I held little hope that this date would turn into anything.

In fact, by the time the day rolled around I had pretty much forgotten about it. When I got a phone call from her confirming that we were still on, I was smack in the middle of celebrating Cinque de Mayo with a group of my buddies at Happy Hour. I had a nice Margarita “buzz” and decided rather than cancel on the poor girl I would just meet her for a few drinks then meet up with buddies again later. I got to the lounge before her and still feeling good from my Tequila “buzz” I began chatting up the bartender. My mood “spiked” and feeling good about my interaction with the bartender, I felt oddly relaxed.

When Marissa (the Portuguese girl) showed up, I was loose, energetic, and completely unattached to the outcome of the date. Fresh from a really entertaining conversation with my friends, I was in no mood for “small talk” so I just jumped right into repeating a funny story my friend had just told me about a custody battle him and his ex were having over a GOLDFISH. (Seriously) As I was telling her the story, instead of putting on my “timid guy” demeanor I began treating her like we were long time lovers, touching her when we talked, taking her hand to lead her to table, and holding eye contact for a split second longer than I normally felt comfortable doing.

And she followed my lead.  (READ MORE)

About Bobby Rio

I'm Bobby Rio, one of the founders of TSB. I tend to write about what is on my mind so you'll find a mix of self development, social dynamics and dating articles/experiences.  For a collection of some of my favorite articles check them out.

Simple Trick Tells You if a Girl Wants You to Kiss Her

Do girls leave you confused as to whether or not they like you?

Let's face it.  Girl's don't make it easy for you.  She will often send mixed signals leaving you unable to tell if she is being friendly or flirty.  If you read her signals wrong you risk rejection and embarrassment. Or worse, you blow it with a girl who wanted to kiss you.

Here is a simple and innocent move that will instantly tell you if you're in the friend zone, or if she's waiting for you to kiss her.


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  4. Richard

    May 6, 2010 at 8:43 pm

    Excellent post Bobby… It’s compeletly true what you say about assuming rapport… for some reason, even though i know this… i still find it hard to overcome

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  6. Jimmy

    May 8, 2010 at 12:00 am

    Excellent post minus the garbage links at the bottom

  7. dude

    May 8, 2010 at 7:59 am

    very nice post . i especially agree with the point of dropping the nice guy act and just being yourself (in a positive way of course). so often i am worried about saying or doing something that may offend a date but it is when i am feeling loose and could care less that end up being the best times.

  8. Michael

    May 9, 2010 at 12:26 pm

    very nice post . i especially agree with the point of dropping the nice guy act and just being yourself (in a positive way of course). so often i am worried about saying or doing something that may offend a date but it is when i am feeling loose and could care less that end up being the best times.

  9. Rob Judge

    May 9, 2010 at 5:07 pm

    Awesome post Bobby. I really like this

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