5 First Date Mistakes Men Make That End In Heartbreak and How To Avoid Them

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Written By: Michael Webb

Let’s face it ­­you never get a second chance to make a first impression!

That’s why, if you want to take things further with a woman, you need to show her your best on the very first date. And in actual fact, there are 5 things that men consistently do on first dates that totally destroy their chances of seeing the woman again, and the worst part is they think they’re doing it right!

Avoid the following 5 mistakes to increase your chances of success on your first date:


Bringing chocolate or flowers on a first date isn’t the best idea – especially if you’ve just met the woman! She’s there to get to know YOU. Women are always asking themselves “what does THAT mean?” And in this case it’s, “He bought me flowers because he likes me, but he doesn’t even know anything about me yet! A little suspicious.


When in the presence of a potential date, men often become boring, instead of keeping up the friendly vibe they have with their friends. They won’t make jokes or laugh with the woman, they don’t play around like they do with their friends and they generally take things a little too seriously. Why do men change their behavior around women, often without even realizing they’re doing it? Because they fear losing their only chance with the girl of their dreams, they try and play the safe side, which results in a “Mr. Serious.”


When men become “Mr. Serious” they often fall into “job interview conversation mode.” Make sure you reserve questions like, “So where do you work?” or “How many brothers and sisters do you have?” for the future, after you’ve already had a lot of fun and made the sparks fly. Instead, talk about your hobbies, interesting stories and fun stuff. Avoid anything too deep for a long period of time. On a first date, it can make things a little depressing. Talk like you’ve known each other for years (as if you don’t need to do the awkward 20-questions quiz.) Of course you can ask basic questions, but never make it the main focus of your date. Focus on fun.


Without realizing it, many guys turn their dates off by trying a little too hard. For example: Men will lean into a woman’s personal space, and ask, “so do you like me?” or constantly change his opinion to seek her approval and make her like him. Big mistake. Ironically, it’s leaning back, staying cool and calm, being a little cheeky, interesting, mysterious and comfortable with yourself that actually gets a woman’s attention and keeps her interested.


If your date finds the night boring, you’re finished. When it comes to having fun on first dates, nothing is more important than what you do. And while dinners and movies are nice, it’s really hard to leave a great impression in these settings. Why? Because they set a very “proper tone” that’s hard to turn into fun and playful. And unless you’re a super funny, intelligent and interesting guy, dinner and movie dates just aren’t the best place to take your date. Instead, go to fun places like mini-golf parks, carnivals, parks, or even better, come up with your own unique and fun ideas.

So in essence, while there are many factors to having a successful date, a great date idea really helps you do many of them naturally! Remember, where you take a woman on a first date can be the difference between a great night and a dating disaster! Choose wisely!

About the author:

Oprah Expert Michael Webb is the author of 300 Creative Dates, a book jam-packed with unique ways to help leave a great first impression without breaking the bank! To learn more or order your copy click here!

So for fun, fill me in on some of your first date blunders…

p.s.  If you feel you may need a little push in the right direction visit my Personal Services Page to determine how I may be able to help!

Are you ready to take the first step and start meeting other relationship minded people?  Would you like help in determining the best way to go about it?  Click the button below so we can make a proactive plan of action!


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17 Responses to “5 First Date Mistakes Men Make That End In Heartbreak and How To Avoid Them”

  1. Denise Iridium

    is leaving their underwear on the floor one of them?;)

  2. Michael Cabnet

    So, do women ever make mistakes on a date???????

  3. Tami Jones Pate

    Oh, yes we do….many of them actually….but..usually talk way too much.

  4. David Messerschmidt

    Hmmm Denise….leaving underwear on the floor on the first date??

  5. Denise Iridium

    like you never have sex on the first date Mr David;p

  6. David Messerschmidt

    Denise… There is a kiss and tell policy!!

  7. David Messerschmidt

    SO … NO!!

  8. Miss MatchMaker

    OMG you guys are cracking me up LOL

  9. Michelle Colon-Johnson

    I have to agree with the author! I like to do fun things! Like recently I had someone invite me to a charity event that was having a soup cook off.. When you got a bowl of soup you were able to pick a hand made bowl out to keep from a local artist!
    I still like to go to dinner but it is usually better if it is a place I have never been before. I like trying new foods. One date I went on we ordered almost the whole Tapas menu. Made the conversation flow!

  10. Miss MatchMaker

    Very good point Michelle! I tell all my clients skip the dinner “interview” process. A lady has gone out on tons of dinner dates, do something fun, something different. Men should want to stand out from all previous dates and to do that he must get creative!!!

  11. Miss MatchMaker

    @ Michael YES we make tons of mistakes as well like Tami said the biggest is that we talk to much! I think both men and women need to find the balance between talking and listening but most importantly as Michael Webb states keep it FUN!!!

  12. Carrie@RelationshipRepair

    I like your ideas. #4 about being too emotional or needy speaks to me. I like a guy who is confident and self assured – not afraid to be himself. And, it;s funny but I’ve been reading lately about all these first date “lists” and most of them are advocating the 20 question type of list. Just like you talked about avoiding. I’m with you, who wants to be grilled? Asking a question or two about interests and then talking about that seems kind of fun, but all those other details – who cares on the first date. Go out and have some fun and see if you have any chemistry.

  13. mikebra

    Hi, Good work!These are great tips. very informative article.Well done! Thanks for sharing ,this is a very detailed article about this subject matter.its really helpful to us.thanks for writing.

  14. Brand Innovation company


    Great stuff with some important details. Surely people will be able find the potentials as how it is written. Thanks for this nice post.

  15. CROWN

    get to you more. its nice

  16. Liz

    I like all of these ideas and am writing a report! I’ll let you know how it turns out and if I got an inspiration from here..;)
    Liz´s last [type] ..Mr. Right 5 Ways to tell if He’s the “One”

  17. 3 greșeli pe care le fac bărbații la prima întâlnire – Tasta

    [...] Sursa [...]

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