No More Missed Opportunities: How to Approach a Guy

ZachBraff_mediumTHERE HE IS, “THE HOTTEST GUY EVER” AND YOU’RE PRETTY SURE HE’S LOOKING AT YOU. Maybe he held the door for you or he helped you reach a box of cereal at the grocery store (I’m short… it happens a lot), and what do you do? You walk away and never see him again.

Like 97% of you, I WAS that girl. (I made up that statistic).

So about a year ago, I made a conscious decision to stop telling lame overly embellished and ridiculously intricate stories of the 10 seconds I shared with some hot guy. And now, according to my friends and this one guy at work, my stories are far more interesting. Basically, the mantra was: Put myself out there and make it happen. No matter what. No regrets.

And…

IT’S AMAZING HOW DRASTICALLY MY DATING LIFE HAS CHANGED. SO NOW THAT I HAVE CONQUERED MY FEAR, I DECIDED IT WAS TIME TO INSPIRE THE OTHER 97% OF YOU TO GROW A PAIR… AND APPROACH.

First off, never make yourself feel too awkward, cheesy, or uncomfortable. The goal here is not to come up with some lame-ass speech and work up the guts to recite it to some guy. You have to get creative both with your tactic and with the particular situation you are in. I like to use what I call the “can you imagine” approach: Try thinking how you would joke with your girlfriend about how you would hit on him, “can you imagine if I just ____________”… Fill in that space and then actually make it happen. You’d be surprised how empowering it is to take control.

Now, in going along with the theme of shit I do that results in crazy stories, I now invite you to hear a few of my favorites…

First up.  I was out for dinner with a girlfriend a few months back, of course looking like total shit (‘cause the hot guys always flock when your hair’s in a messy bun on the top of your head). On our way out of the restaurant I spotted a table containing four attractive male specimens, one of which caught my eye. And I apparently I caught his, then we caught eachother’s. We both laughed a little. I kept walking. Cranked my neck back for a final au revoir and vanished onto the side street.  And that was it, our only interaction. SO, WHAT DOES THE NEW CARA DO? I PULL AN OLD RECEIPT OUT OF MY PURSE, WRITE ON IT “I DON’T BELIEVE IN MISSED OPPORTUNITIES” ALONG WITH MY DIGITS AND HAVE MY FRIEND STRUT BACK OVER AND DELIVER IT TO WHAT IS HOPEFULLY THE RIGHT GUY. I hear a laugh from the table and know that whatever happens, I can go to bed with no regrets. The next day I get a text from my cute new guy who apparently thinks my stank face is “gorgeous,” which is great! But he was an actor. And for all of my LA readers that is ‘nough said. Bottom line is, I liked what I saw and I made it happen. Nothing to lose. Plus he LOVED being approached and better yet his friends were totes jealous of the ballsy interaction.

The thing is, guys think it’s hot when they’re approached. Chances are if you put yourself out there, he’ll at least be nice to your face. I MEAN, I’M GOING TO BE REALLY RUDE HERE FOR A SECOND, BUT IF YOU’RE A 5 AND HE’S A 9, THEN HE’S PROBABLY NOT LOOKING AT YOU THE WAY YOUR DISTORTED MIND THINKS HE’S LOOKING AT YOU, SO DON’T BOTHER. The situation has to be right. If you feel a little chemistry then trust your instinct and act. As an example, and for some “grow-a-pair” inspiration you should check out one of my most famous blog posts, often referred to as the “Virgin America Guy.” If you haven’t read it then you need to. This is not a shameless plug, well maybe it sort of is, but I promise the read is well worth it. The long and the short? Basically, it was my first major “hit on a guy moment.” Virgin America Flight. Touch screen seat-to-seat chat. 10-day whirlwind romance. Hotel room service. Shooting stars. Epic.

Okay movin’ on. This one you’re going to love and will explain the “letter” image for this post. Now, this is a very LA story, and verging on stalker, so please don’t judge. However, if you feel compelled to reach out to the B-list celeb that I will be referring to and drop a good word for me that would be greatly appreciated. Aight, so I had some friends in town. Fast forward to Saturday night, ‘cause all twenty-something tourists need to hit up a club they read about in US Weekly. WE’RE STANDING NEAR THE BAR DANCING AWAY DOIN’ THE “I’M HERE TO DANCE IN A CIRCLE WITH MY GIRLS, LIP SYNC THE WORDS TO SONGS I LIKE, NOW FUCK OFF SKINNY DRUNK BOYS WITH WEIRD POSTURE” DANCE. And who rolls in? None other than the cutest, funniest, Jew-boy alive… MR. ZACH BRAFF. Naturally he chooses to sit at a table directly beside where we are dancing. A few minutes go by and my girlfriend grabs me and yells in my ear over the My Humps remix, “Zach is totally staring at you.” My first thought is, “apparently we are now on a first name basis,” and my second thought is, “there’s no way.” But he was. I didn’t want to be annoying like all of the other girls draped over his table so I played it cool and didn’t approach. We literally stared at each other for an hour. I got annoyed with his lack of balls and walked away, heard his friend (that guy from Clueless and Scrubs- I don’t think anyone knows his real name) say “dude she’s getting away.” Oh man. Anyway this ensued for another hour and I refused to be a star-fucker so I never approached. Felt real stupid after. So the next day I’m out for dinner with a friend and of course I tell her the story and that I’m a lame-ass. And then the most random thing happens, she tells me that our friend works at the gym he works out at (yeah I know, only in LA). So not to be forgotten, I handwrite a witty-ass letter (seen on left page) to be delivered to his sweaty self. Yeah I’m pretty much a stalker, but I figured what the hell. In the end, the letter was delivered. Apparently he gave a little laugh and said he didn’t approach because he had a girlfriend. Yep even lamer. But he still has the note with my digits for future use…so maybe one day Zachy baby… one day;)

Last story. This one is about the great guy with great hair from my last blog. Update: we are no longer dating, but he’s still a great guy and I’m sure he still has great hair. Okay, so I was out at a bar (wow just realized I’m sounding like a party animal, I swear I’m really not) with friends and decided to leave early. So I walked to the valet, and stood shivering with my arms-crossed in the cold Los Angeles air;) Up walks Mr. Smooth (who is slightly inebriated) “what’s up arms crossed?” I loved his segway so we chatted for all of 8 seconds before my car pulled up. I hopped in and proceeded to drive off. He puts his hand to his ear and jokingly mouths the words “call me.” So, because neither of us have each other’s numbers, I PULL OVER AND OPEN MY WINDOW TO SUMMON HIM OVER. AFTER RAGGING ON HIM FOR NOT ASKING IN THE FIRST PLACE, I GIVE HIM MY DIGITS AND WATCH HIS DRUNK LITTLE FINGERS TRY AND TYPE IN MY NUMBER. OBVIOUSLY I NEVER HEARD FROM HIM AGAIN BECAUSE HE REFUSED TO SEARCH “GIRL FROM VALET OUTSIDE OF WINSTON’S” ON HIS PHONE. A week or so later I’m on my Facebook newsfeed and a friend’s picture pops up. I click on it. And who’s in the picture? Him. Six mutual friends and Jewish. Goldmine! So harnessing the extreme power of the FB, (I did not add him, important to note), I shot him a quick message titled “It’s a small small world.” It was cute, short, not crazy and everything started from there. And I guess ended. So be it. But at least I made it happen and gained a great (but short lived) relationship out of it.

So, whether he’s a guy at the Apple store or he’s sitting in front of you at the theatre, all I can say is go for it. You honestly have nothing to lose. And that’s really it. Just be creative, man-up and put it all out there. And if you don’t know what to do… tweet me (@Hes_THAT_guy_) or email me (advice@hesthatguy.net) and I will help you come up with something. I REALIZE THAT NONE OF THESE GUYS HAVE BEEN “THE ONE” BUT AT LEAST I’M GAINING GREAT EXPERIENCES, SOME GOOD DATES, AND MOST IMPORTANTLY THE CONFIDENCE AND SENSE OF EMPOWERMENT THAT COMES WITH TAKING CONTROL.

7 Responses Subscribe to comments


  1. Christineee

    Wow, this is what I seriously needed.
    Thanks for the wake up call! (:

    Jul 27, 2010 @ 4:11 pm


  2. Kathy

    Totally loving your blog! Definitely time for me to grow a pair!

    Aug 03, 2010 @ 9:56 am


  3. Latricia Benning

    There are certainly a good deal of details like that to take into consideration.

    Aug 04, 2010 @ 4:33 pm


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  7. Erika

    I googled “how to approach a guy you’ve never met” and this came up. I had a really good laugh. You write very well, I’m not sure if that is a passion of yours. It is very conversational, but formal at the same time. I can feel you talking to me, yet I still know you are talking to a group of pathetic girls like me. I’ve handed out my number ONCE and it was to prove a point to my little cousins that you have to be strong and go for what you want… Yeah, he called me, we had a fling for a couple weeks, but that’s all over now.

    I’m sitting in a coffee shop and we’ve made eye contact about a dozen times. I can’t help but smile at him. Blablabla, there were little “sparks” but of course, what if that was just on MY end?

    I’m thinking about dropping my number, but I’m not sure. There are other people around and I’m alone. I don’t know how to react or get his attention. This is the first time I’ve ever met him.

    I liked your “I don’t believe in missing opportunities” thing. It was very cute.

    I know i’m sending you this over a year later… but BLAH!

    Nov 02, 2011 @ 10:30 am

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