How You Can Instantly Get Over Being Insecure On a Date

happy female being embraced by sporty man

Last year I went skiing for the second time in my life with my wife and another couple. The other couple was experienced. My wife had gone a bunch of times before we met. That left me completely alone as the novice of the group.

So after four hours of lessons in Big Bear — practicing the snowplow while surrounded by 5-year-olds — it was time to take the chairlift up the mountain for my first run.

I was INCREDIBLY nervous.

I felt an intense fear in the pit of my stomach, and barely spoke to my wife on the way up.

I was worried about embarrassing myself in front of friends, tearing my ACL, and any other number of things that could happen from the top of the mountain to the bottom.

Then, I looked down and watched the effortless slaloming of hundreds of children. I suddenly realized that my fear was MADE-UP. If millions of people enjoy skiing — and do it without having a heart attack — that meant I had to push through my own paralysis.

Two hours and 8 runs down the mountain and I discovered that I ENJOYED skiing.

We all have fears — and no, we can’t merely think them away — but I think it’s essential to work to overcome them, instead of letting them run your life.

In spite of the fact that I sometimes felt like I was careening out of control.
In spite of the fact that pretty much everyone else looked better than I did.
In spite of the fact that I once slid directly into a tree.

In fact, skiing was FAR more fun than I thought it was going to be. And while I’ll never be an Olympian, I can see myself getting good enough so that I will be able to ski with my friends instead of the 6-year-olds.

Why do I share this story with you? Because the fear I was having was not all that different than the fear you might have when it comes to dating.

It’s a fear of looking bad
It’s a fear of embarrassing yourself
It’s a fear of doing the wrong thing and getting hurt.

But most of all, it’s a fear that’s fundamentally IRRATIONAL.

We all have fears — and no, we can’t merely think them away — but I think it’s essential to work to overcome them, instead of letting them run your life.

It’s a funny thing when you think about first date fears.

Really, what’s the worst thing that can happen on a date? You don’t get a second date? You might turn into someone else’s “bad date” story? You have an uncomfortable 90 minutes that you wish you could have back?

The stakes are so low, so unimportant, that it’s a wonder that dating brings these feelings out in us. But it does. And when your fears cloud your judgment, they can turn something as benign as meeting a new person into an anxiety-ridden tension-fest.

Thus, your real challenge is to acknowledge your fear and push it aside.

So what if you’re inexperienced at dating? If you’ve been married for fifteen years and are just starting on, you SHOULD be inexperienced.

So what if you’re a little awkward around the opposite sex? Unless you have a lot of practice in such social situations, you SHOULDN’T be a natural.

So what if you’ve been burned in a previous relationship? The only people who haven’t been hurt are the people who haven’t loved at all.

It’s just like me and skiing — of course I’m going to be a bad skier if I haven’t skied in nearly 40 years. Of course I’m going to be afraid of hurting myself and looking bad. But I also know that other people seem to enjoy skiing, and the more I do it, the more I’ll enjoy it as well. Same with dating.

Unless you get more PRACTICE at it, you’re probably not going to get any better at it.

So when you read my nagging articles about how love takes effort, or about how online dating is amazing if you know how to use it, please understand where I’m coming from.

I’ve loved. I’ve lost.
I’ve been afraid. I’ve been rejected.
I’ve dusted myself off – and dated and dated and dated — and finally got married — after over 300 dates.

So I’m not talking to you as a guy who is a natural — no more than I’m a natural skier. I’m talking to you as a guy who, thru sheer determination and lots of practice, found love.

So what if you’ve been burned in a previous relationship? The only people who haven’t been hurt are the people who haven’t loved at all.

So while I don’t know you personally, I know there’s a reason you signed up for my newsletter or read my blog : something’s not working in your love life.

You don’t meet enough people.
You don’t know how attract the people you want.
You don’t know how to distinguish between a good catch and a bad catch.
You don’t know why your last date broke it off.
You don’t know what you can do differently to get a different result.

Well, I’m here to tell you — as a guy who was literally the WORST skier at Big Bear:

You MUST ignore your fear.
You MUST get more experience and practice.
You MUST get back up when you fall.
You MUST learn what’s not working for you and correct it.

Have you been on only a few dates in the past three months?

Have you been afraid of looking bad in front of a cute guy?

Have you been burned by a boyfriend and are unsure about what to do the next time around?

Then ignore your fear and keep practicing.

Remember, you don’t have to be a ski instructor to have fun on the slopes.

You just have to get back up when you fall.

Join our conversation (14 Comments).
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  1. 1
    Flower White


  2. 2

    Absolutely. Havent commented in ages, but this rang Norte Dame worthy bells with me. Its like anything u do. Dan Savage said once “Every relationship you have will not work out, until one DOES” Doesn’t mean every relationship is a failure, you learn about yourself, what you want, what you dont, what drives other crazy about you (in good and bad ways) and, for a first date, the worst ones are the best stories. Of course.  

  3. 3
    my honest answer

    That’s so true Evan! My mantra in life is, ‘what’s the worst that can happen’, and I usually find that the answer is that someone says ‘no’. It’s a really helpful way of putting things in perspective, because usually the fear is of something fairly insignificant.  
    Physical fear is a different thing for me somehow though. I ski (and love it!), but rollercoasters? Um, no thanks.

  4. 4

    When my friends get bunged-up over trying something new, particularly dating, I say, “If nothing else, at least  you’ll have a funny story to tell.” It instantly puts things in perspective.

  5. 5

    This was great Evan!   Perfect timing.

  6. 6

    What’s  the dating equivalent of your 4 hours of training?

  7. 7

    You know, I’ve gotten over my fears by simply taking the “romance card” out of the thought process.   Why is it people put on huge expectations of a future relationship when meeting a particular person when they barely know  them or how they are??   Inexperience does that I think.  

    I decided to adopt a “freind” attitude to everyone I meet online…and to ensure awkwardness doesn’t happen, I’m upfront in communicating to them that I don’t “date” persay.   I always say I’m burnt out on “dating” and I just like meeting new people in order to converse and hang out as friends.   This takes the expectations off of me and off of them and puts us both in  a frame of mind to  just let stuff happen naturally instead of being awkward and uncomfortable. :p

  8. 8
    Karl R

    Evan said:
    “It’s a fear of looking bad
    It’s a fear of embarrassing yourself
    It’s a fear of doing the wrong thing and getting hurt.”

    I agree that it’s irrational (if human) to worry about these things. If anything, the stakes are even lower than you imply.

    Have you ever been on a first  date with someone who tripped or did something awkward, but you chose to go on a second date because you liked them? I have.

    Have you ever been on a first  date with someone who misspoke or got tongue-tied, but you chose to go on a second date because you liked them? I have.

    If a person likes you, you can accidentally spill a bowl of soup in your lap (or their lap) and still get a second date. It’s really hard to screw this up.

    In contrast, I look at the women that I chose not to go on a second date with:
    – I found one unattractive.
    – One was moving out of state in a few months.
    – One was too young for my tastes.
    – One wasn’t intelligent enough for me.
    – One was an ultra-conservative Christian.

    In each case, I decided against a second date due to things the women couldn’t change (looks, age, intelligence) or they wouldn’t change (religion, career-advancement).

    I either get (or fail to get) a second date based on what I am, not what I do. Since the outcome is out of my control, what is there to worry about?

  9. 9
    Bree Talon

    Sometimes when I want to be good at something, I get really impatient with myself and lose sight of the process that’s required to really be awesome. Funny how hard we are on ourselves!  It took me a long time to be an awesome mountain biker. I had to fall and crash and ride on all kinds of terrain to really kick ass. It’s a great reminder that anything worth doing is worth doing well…and I appreciate being reminded that this applies to our love lives as well as our personal goals and accomplishments.
    @Karl R, love your comment about  being willing to go on  date with someone who didn’t do everything  just right on the first date  – because you liked them – that’s  where it’s at in my opinion. Reminds me of  something I like to tell myself, which is “people  will forget what you say,  and they will forget what you do – but they will never forget  how you make them feel.”

  10. 10
    Darren Miller

    This post sounds just like my girlfriend. She is very fearful of people ‘looking down’ on her and judging her. I recently   taught her to swim and she was always aware that she was in the training pool with the little children.

    It is true everyone has experienced fear, whether it is of spiders, heights, judgment or rejection. The only thing you can do is learn to beat them and don’t let them stop you from doing anything you want to do.

    Don’t fear dates. Just be yourself and you will find the person meant for you.   Yes, you will have to kiss a few frogs along the way but don’t be put down by the dates that don’t progress. They aren’t meant to be.
    Hey, Evan….  
    By the way, I wanted to let you know that I am linking to your site and have been for some time.   You have an excellent site and would be honored if you would consider linking to my site as well.
    My site, which is called The Relationship Spot, is located at:

  11. 11

    My view is that the more nervous you are about dating, the more dates you should go on. That way, it becomes “routine” , so that when you DO meet someone on a date you actually like and want to see again, you’re NOT nervous and don’t mess it up. The wors scenario, i think, is to have to go on a date with someone you’re REALLY interested in, having not been on a date for years. The nerves would be overwhelming.
    I get what Karl is saying, that its not nerves that put him off, but as a woman I would have to say I HAVE been put off on dates by men who were too nervous. A girl who is a bit nervous might come across as a little shy and endearing, but a nervous man is quite a turn off – confidence is attractive in both sexes but I think its even more important for the man to be confident.Someone who fidgets nervously at the bar, can’t seem to get the attention of the waiter or talks non stop about whaterver enters his head is just…well…not manly!

  12. 12
    Raymond Bork

    Most of us never manage to overcome the fear of meeting up for a date for the first time. Evan is right, we just can’t think our fears away, but we can alter our perception of that first date experience. By lowering ours and our date’s expectations we can make it much easier for both of us.
    Arrange to meet for a 30 minute coffee date, where it’s just a quick ‘see if you get on well enough for a longer second date’ exercise.
    The coffee date costs are negligible, and it’s a safe environment. Dressing up is no more than smart casual, and you can just hug your date, if you want, without any thoughts of expecting to kiss each other.  
    Before the date repeat some positive affirmations like, “I feel great, because I’m going to have a wonderful time!”.   If you need help, there are loads of affirmations that will suit you, you only need to Google them.
    Focus on the perceived positive dating experience you are expecting rather than the fear of it!

  13. 13

    @ Karl #8,

    I either get (or fail to get) a second date based on what I  am, not what I  do. Since the outcome is out of my control, what is there to worry about?  

    I agree with what you’re saying Karl, but to play devil’s advocate, some of us are trained early on that we have to win people over based on what we do, not that some people will like us because of who we are and some people won’t.   It’s tough to unlearn that.  

  14. 14

    I know a woman that married the man she wished   had died while on his way to the bathroom during the first and second date.   They have been married 25+ years and have 3 wonderful children.    

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