Good Date Gone Bad | 7 Dating Mistakes Men Make

dating mistakes men makeLast night I was looking at our Christmas Day website traffic. Not only was it a lot higher than I anticipated (about 400 readers for the holiday), I was really surprised by what people were reading. The top articles were almost all about relationships. Our most read article during Christmas Day was 8 Reasons Why You Keep Getting Dumped. Isn’t that sad?? I recently was asked to begin writing a dating column for an alumni association I’m a part of, and Fearless Men is now featured on the Man Up Leadership App. With the requests we’ve been getting combined with what our readers were reading, I decided it’s time to write about Dating Mistakes Men Make.

Of course you can read the article on Getting Dumped, and John’s insight on How to Make Her Feel Special and First Date Tips will certainly get you rolling in the right direction. But have you ever headed out for a date confident it’s going to go great and things fall flat? Maybe you’ve been on several dates and somehow the oxygen gets sucked out of the budding attraction and things are suddenly dead on arrival? Learn what dating mistakes may be happening.

It’s not time to be frustrated with yourself or your dates. Let’s take stock and consider a few points that might be going wrong. Since the Getting Dumped article mentioned earlier is aimed at those that have been in a relationship for a while, I’m aiming this one at those men that have only been out on 1-5 dates.

Dating Mistake 1: You Don’t Have a Goal

I always aim to get to know one new, deep thing about a woman each time I’m out with her. I don’t put pressure on myself to know her life history or her plans for the future right away. I just aim to ask at least one good question, and take the rest of the date as pretty chill. Just go in without feeling the pressure to impress or know her life’s calling.

If it’s a first date, you MUST have a 2nd goal, and that’s to nail down your next date. You don’t have to plan exactly what you’re doing, but set a day and time. Why? You want to keep the ball rolling while things are still warm. Don’t let her lose interest, and don’t let her walk away from the date thinking you didn’t enjoy the date enough to see her again.

If you don’t ask her out for the sequel by the end of Part I, the next time you try to communicate you should anticipate she’ll be in what some people call “auto-rejection” mode. You haven’t actually rejected her, but she may feel that way and be ruminating through those thoughts. Don’t be surprised therefore if she’s distant or slow to communicate with you about Part 2.

Dating Mistake 2: Playing the Waiting Game Like a Fool

dating mistakes men make

Don’t let that horse get out of the gate too fast.

I don’t play waiting games. If I’m attracted to someone and we’re clicking, then I tell them I want to go out again. I’m not going to sit idly by like a passive boy waiting for her to chase me. If she likes me enough to go out with me again, then she’ll say yes. If she’s non-committal or distant, then I already know it’s not there and I don’t have time to pine away for her.

Listen, we’ve all got lots to do on this rock before we’re dead, so don’t make her wait 48 hours to tell her you want to go out again. If she puts you off after one or two dates, ask her out one more time and if she’s still cool toward you, move on man. There actually are other women out there. You were brave enough to ask this one out so just go do it again.

Now…if you’re already in a rhythm and have been on a few dates, you don’t have to feel the pressure to seal up the next date immediately. Once you guys have found a good pace, rushing to set the next time you’re going to be together probably isn’t necessary. Unless they ask. Then be polite and try to figure it out. Or at least tell them you def want to get back together and need to figure out what works.

There’s a lot of bullshit out there about waiting days after a date to call a girl. Don’t listen to that nonsense. Are you a player or are you interested? If you want to torpedo your chances with a fine lady feel free to take that advice.

Let’s get practical
dating mistakes men make

“Oh God, I’ve never received a call on my phone before!”

If you want some practical advice, here’s mine. I could be totally wrong, but I think this is better wisdom than the average player advice out there:

  • Before your first date is over, tell her you’d like to see her again and decide when is a good time.
  • Don’t set up your next date any quicker than 4 days from now. Give yourselves a little breathing room.
    • Why? It’s always easy down the road to speed up the pace than it is to slow it down. If you burst out of the gate running, in a couple weeks if you guys are hanging out every other night and you’re having second thoughts, it’s hard to slow that horsie down.
  • Text her within 4 hours of the date. Let her know you had a great time and are looking forward to seeing her again. Just don’t make her feel like you’re professing your love.
  • Call her within a couple days. Leave her a short and sweet voicemail that you just wanted to check in and say “Hey.”
    • If she doesn’t pick up or call back it’s totally cool. If you’re dating someone less than 27 she might be allergic to phone calls anyway. But I still like to use them.

Dating Do: Be an Affirming Man

Find out something she’s excelling in and why she’s great at it. Then tell her why she’s so awesome. Make her feel attractive, but if you merely tell a woman she’s hot, not why—then you might be coming off as a sleeze. Try to find something uniquely attractive about her that you wouldn’t notice in other women. Point it out—it’ll mean a lot to her.

Again, compliments need to be original. They should be about how pretty she is, but they should also be about so much more. Find out why she’s incredible, and tell her what you’ve noticed. Slightly, casually, while giving her your focused attention.

If you can’t find something great and unique about her, you either don’t like her or you spend so much time talking and thinking about yourself you didn’t notice the gem she is.

Dating Mistake 3: Not Flirting

When I was 20 I was about to see a girl that I’d liked for a year but hadn’t seen in several months. I asked a mutual friend of ours, who is a woman, for some advice. She gave me one piece: don’t forget to flirt with her. I was confused, and asked her why she’d suggest that. She told me that sometimes guys forget to make a girl feel like he’s actually interested in her.

I think as men when we’re really attracted to and legitimately interested in a woman we sometimes become dead stiffs. Ever feel the cold sweat in your hands as you literally have nothing intelligent to say? Yeah, I feel ya. Make sure to bring your brain, and a little bit of heat. If you don’t show that you’re attracted and find her likeable, she probably won’t feel much of a spark. That’s a dating mistake men make.

Have you been out with a woman that was a total stiff toward you? You probably didn’t feel she was interested, and you’re attraction for her probably took a jolt too.

Dating Mistake 4: Being a Jerk Without Even Knowing It

Were you a jerk or were you nice? You might be quick to answer that you of course weren’t a jerk. But consider this: were you on time? Did you buy the meal/drink? Did you show up in a rush, sweaty, and kept looking at your phone the whole time?

If you didn’t show up ready, on time, and focused enough to give her your undivided attention, you might have come off as a jerk even if you didn’t say anything rude.

Dating Mistake 5: OCD

The flip-side of showing up with the tenacity to make her your entire world and make her feel like the center of the universe is this: you can totally freak her out. If you’re gazing through her face with the force of Superman’s Heat Vision and neglect to realize or refer to anything outside of her two-foot personal space, you might be coming off too strong.

dating mistakes men make

“I only have eyes for you, baby.”

 Dating Mistake 6: You’re hung-up on her and she knows it

If you’re hung-up on a girl within the first 3 dates, it’s going to be hard to not show it. You’re really attracted to a lady and love her company. You want it to work out so bad you feel the pressure to perform. Once this pressure builds, you’ll start to “grip” onto a relationship you never had.

Don’t let this level of desire for a woman build up-yet. If you are feeling that strong for a girl that quickly, you might be acting funny towards her. Inconsistent or extra emotionally sensitive. And that sucks the fun out of the fun stage of a relationship. Hey, as men we don’t like feeling pressured to be in love before we’re ready to be, right? Women don’t like to feel that way either.

If you’re dying to have this girl and are feeling a potential major letdown if you don’t win her–you’ve got to reduce the pressure on yourself man. You won’t act like yourself,  and you won’t make her feel comfortable.

You’ve got to kill the tension while you’re on dates. Especially dates 3, 4, 5. Those dates are where a woman is wondering if a guy IS getting seriously interested in her or not. But if you go into those dates and you’re all wound up-it’ll be tense and you might kill off some of her interest. She may not know why, but she could possibly start feeling like the first 2 dates were great, “But I’m really not feeling it there between us anymore.” Don’t get sucked into that hole.

Here’s what I do to relieve the pressure on me: I know that not every woman will like me. In fact, most women don’t.

It’s really freeing to acknowledge this. Most women aren’t interested in me. Boom. If she changes her mind about me, no big deal. She’s not a bad person, and that doesn’t speak to whether or not I’m a good or bad guy.

If you can walk into a date carefree whether she accepts you or not, you won’t pander to try to endlessly impress her. Men who do that don’t come off as confident, rather they come off as people pleasers. And trust me, women aren’t drawn to that at all.

Dating Mistake 7: You don’t have any direction

So you’ve been out several times, now what? We don’t have space to cover that here, but at some point you’ve got to have a plan. If you’ve been out on 5 dates and you haven’t communicated with your lady friend whether your want to continue being casual, break it off, or really make an effort to get closer to her, your lack of direction may actually be allowing the “relationship” to die without your knowing it.

You don’t need to propose or tell her you love her. Just sit down with her and define together where you’re at, and where you’re going. Even if that means keeping the same pace and trajectory you’re at today.


  1. I’m so happy I’m done with all of that!

    I especially liked, “If you’re dating someone less than 27 she might be allergic to phone calls anyway.” I’m pretty much the only person my wife will answer the phone for. Everyone else she makes me answer her phone or lets it go to voicemail.

    • Todd Mayfield says

      Bro it is so true. I think even women, well I guess even myself included, are becoming more and more allergic to picking up the phone!!

  2. Very interesting to read from a male perspective. I haven’t been in the dating world for so long it’s hard to remember what that was like.

  3. Hi Todd

    Terrific article however I don’t wholeheartedly agree with it.

    How do you explain nicer guys that follow the rules written on the Internet don’t get the girl after going on several dates. Meanwhile the so called Badboy/player gets the girl hooked rather immediately?

    I would add being boring or too shy to the list. Having charisma and enthusiasm + coming across as exciting goes a long, long way. Badboy thing working more often than none has been a head scratcher forever.

    • You know, we’ve been wanting to write an article on how to NOT be the nice guy that never loses the girl. If you have any thoughts, let me know.

      As for this article, I think points 3, 5, 6, 7 all have to deal with a bit of the “nice guy” syndrome. Badasses know what they want, they flirt, they are direct, and they aren’t desperate for the girl. That makes them elusive and desirable–sometimes.

      • Hi Todd

        Thanks for acknowledging my comment (See? I am polite but it hasn’t gotten me far in many occasions personally & professionally)

        Here is my advice to so called “Nice” guys, ESPECIALLY when dealing with worldly women as they know the ropes.

        1, Don’t bend backwards right off the bat. That’s the biggest mistake anyone can make. My sincerest of apologies as I don’t want to offend; but don’t kiss her behind when you barely even know her. That’s different from complimenting her though. It goes a long way particularly when you notice the little things.
        2. Don’t be available all the time. You don’t have to pick up right away OR text back instantaneously.
        3. People who are accommodating to no end, agree with all her points, and too pleasing; come across as aloof. Look it up guys!
        4. Don’t get her a bouquet of flowers on first date. You will come across as desperate. Don’t hand her Chocolate or the finest import champagne. If it is her birthday and you just found out, a single rose or a thoughtful card will do wonders.
        5. Show enthusiasm and Charisma (As mentioned above in my previous comment). Don’t do that and you will have game/set/match.

        Not all the girls/women are the same but driven / worldly women can give a so called nice man fits.

        Once again; terrific article Todd.


        • Hey Mikey,

          Great thoughts. I just wrote on “How To Get Out of The Friend Zone” and I think your thoughts above would fit well into a “How To Not Get Into” or “How To Not Start Off in the Friend Zone.” If you’re ever interested in writing something like that, let me know!


  4. 340Massive says

    Good advice. I’ll add that the best approach I found is to work on your fundamentals so that you don’t have to care so much whether she likes you or not. Instead focus on whether or not you like her. It is so much easier and more natural to progress things forward more confidently and quickly with a woman that you like than it is worrying about whether or not she likes you. So have a clear objective in mind and have a process in place. Ask questions designed to reveal her thought processes/opinions to see if you like her and ONLY if you do then move on to flirting, asking deep questions, to touching, sexualizing the conversation, escalating, inviting home, etc… You will get rejected sometimes but eventually after meeting enough women it becomes automatic and easy to date.

    And another thing why are you waiting until date 5,6,7 to make a move? Girls like sex plain and simple never let them tell they don’t. IAnd depending on the city you live in and the level of attractiveness of the woman you take out, there are very likely alot of other men gaming for your girl. They will continue to approach her and try to seduce her when you are not around, so if you don’t make a profound impact on her emotions (connection + sexual) and they are better and more able than you to take her to bed fast, guess what will happen to you? She will become more cold and distant and you will think that you did something wrong that she “auto-rejected” you. But sometimes what happens is another better and more able man moved more quickly than you. So no benefit to moving slowly and have her attraction will fade…move fast. If you don’t then the best that can happen for you is that you become a “boyfriend candidate” in her eyes which means she holds more power than you… but women are most attracted to the most powerful sexy men that confidently move things along swiftly. And if for some reason she really does like you and not the other guys once you go into “boyfriend candidate” mode she will be on her best behavior and will slow things down and act like a goody goody and fail tell you all the real dark details about her. You will fall in love with the good version of her and in a year after the romance has faded guess what will happen to you? You’ll say to yourself “she’s changed!” She never changed, she just played the game very well.

    So be smart in the beginning and make sure you screen women out well before committing your time and energy. And move fast if you really like her. Dating is just a construct by society designed to get people who like each other to mate. Does it really take you so long to want to mate with someone? Stop wasting time and move fast.

  5. Why do I have to be affirming toward her, why not she toward me? Do you believe a man has to prove his worth to a woman?

    • Oh, if she’s never affirming? There definitely is no shot at a relationship there. And the date won’t be fun either. She definitely she be affirming.

      I think it should be reciprocated. But this is a list as to some of the reasons why a good date in man’s mind might have actually been bad in the woman’s mind. Or for the clueless!

      Does man have to prove his worth to a woman? I don’t think he “has” to take big-time serious actions to prove his worth. If he’s not an affirming person, he needs to learn how to be one b/c a woman will want that.

  6. I dated many men before and I don’t like it! They usually done all that things. But when my last boyfriend came (husband now), he was really different with all those guys. And I’m happy for it.

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