For Single Guys

The Number One Mistake Nice Guys Make and What You Can Learn from a Pick-Up Artist

So this is kind of a follow up from my last article addressed to women. This article is long, so bare with me. I felt the need to include comments from women on this blog as to make my point crystal clear, and to show you proof that I’m not the only one who feels this way. This article is for single men looking to be in a relationship. And this time calls for ACTION and DETERMINATION.

What Most Guys Email Me About

You don’t know how many emails and comments I get from single men who tell me “She said this… then I said that… I catch her staring…” and all they really want to know is “DOES SHE LIKE ME?”

From my experience counseling hundreds of guys over the years on this blog, I’ve made the conclusion that

    the number ONE mistake nice guys make when it comes to the opposite sex is that they wait too long to make a move because they are TOO CAUGHT UP TRYING TO FIGURE OUT IF THE GIRL IS INTERESTED.

Why She Ends up Falling for Some Other Smuck

All the while they wonder why she’s falling for some other guy when they’ve been there the whole time. Why is she falling for some other guy when I’ve been giving her emotional support? Because he’s the one willing to take the risk, and he’s the one making her feel desirable. Giving women emotional support without first being clear that you want her romantically is the BIGGEST WASTE OF TIME.

What You Can Learn from A Pick-Up Artist

The biggest thing you can learn from pick-up artists and players is that they don’t over think whether or not a woman is interested. They don’t care if the women is not interested at first because they know it’s their job is to make her interested. Maybe they know this, may be they don’t, but women will always be more attracted to men who initiate.

Here’s some proof from female commenters:

Awsum!! i’m a nice girl (IMO=)) looking for a truly nice guy..i did get sidetracked by a jerk first because he took the initiative and the other (nice) guys were more laid back..but after coming to my senses i’m single till a MAN comes along. -no matter how long it takes!! kudos to all the “nice” guys/girls out there=)


haha, your advice is cool. i think more guys should be more like that. taking initiative of the whole mood and going for it too. i know guys have feelings as girls and don’t show it, but i think it’s cool if they do show it instead of acting cool, it’s really hard to tell what they are feeling or when they are actually being honest with you then just joking around. us girls sometimes have to make the moves first before the boys. we do hate that. be straight forward..We like that you know. i think confidence is in everyones mind right now. anyways it’s my opinion. thanx for this post. its nice to see what a guy thinks.


Hmm, the “nice, only-friend” guy seems a little bitter lol. It is true that nice guys don’t always get the attention they deserve, but that isn’t just girls’ fault. If you like someone, nice guys, take the step forward and let her know. If she rejects you, then try elsewhere. There are many girls out there, and you can’t let one or ten or twenty failures stop you from finding someone special. Give it a go!

However, if you are experiencing unrequited love, there isn’t much you can do a lot of the time. You can’t force someone to be attracted to you, and that has nothing to do with being nice or not nice.

Personally I like men who take initiative. My boyfriend is nice and takes initiative. He is a wonderful person and I love when he calls me beautiful. And he definitely likes when I kiss him in front of friends.

Cici, I hope you feel better. Don’t be afraid to feel all your feelings, even the ones that hurt.

-Angie Chelle-

Guys, don’t expect the girl to make the first move. She’s not going to come up to you and give you some long lingering kiss on the cheek and expect you go figure it out. Although some girls will make the first move, they appreciate it when guys do, and guys look more confident (aka more attractive and manly) when they do.

Commenter Nat makes another good point!

I think the nice guy doesn’t get seen as more than a friend because girls just don’t notice he likes them. They know he’s nice to them and to people in general, so everything he does they just write off as him being their friend. I know I used to have a guy-friend that could have liked me for all I know, but we were so close I wouldn’t have noticed unless he decided to tell me or hold my hand or something. (Since he never did, well… I hope he didn’t like me, because he really was the nicest guy I’ve ever known and I’d hate to of missed him…)

It’s actually a good thing, I suppose, because you want your boyfriend/husband to be your best friend, not just some guy who’s constantly telling you how sexy you are. (not saying he shouldn’t do that – but just that isn’t enough.) The only problem is that, until you are in a relationship, nice guys seem to often feel like they shouldn’t overtly express their feelings for the girl unless she’s shown it’s alright, but since their more subtle hints get lost in the friendship unless he just goes out and tells her, she has no idea. Since she doesn’t notice and just acts like friends, he’s scared to tell her his feelings because he doesn’t want to ruin the friendship. Vicious cycle!

An Example of A Man NOT Making a Move because He is a Pussy

In this movie, Something Borrowed (which I loved btw), Dex never made a move on Rachel back in Law school because he didn’t have enough evidence that she liked him. That’s the only reason why there’s a conflict in this movie. If he would have just gone after the girl he really wanted to begin with, and if he wasn’t such a coward, this movie wouldn’t have a plot.

Dex is the “nice guy” who won’t make a move unless there’s no risk involved. And this seems to be a trend with many readers on this blog.

Here’s what a reader said:

” If she is interested, i dont mind asking her out but im still confused as to whether she is interested in me or whether it was all a…..coincidence?”

And to that I say, how is a woman supposed to feel about you not being willing to take any risks for her? I have no idea what that woman is thinking. Nobody knows. Only her. I don’t know if she meant to stare or if he was actually staring and she caught him. The point isn’t if she’s interested, the point is that HE is interested and should just GO FOR IT.

The guys who get the girl are the ones who don’t expect the woman to be interested at first. This wise guy knows that it’s his job to convince the woman that he’s worth getting to know. It’s his job to make her interested.

Men and Women Crush Differently

Why is it this way? What you have to understand is that men and women are wired differently. Whereas men can start crushing HARD for a girl, just because she is attractive and mysterious, for a woman to fall hard, it usually takes a man’s persistence and demonstration that he WANTS her and is going to win her over that ACTUALLY makes a woman fall.

She takes into account looks, charm, humor, personality, etc… but it is a man’s pursuit of her that sends her over the top. So to try and think that a woman is interested right off the bat, just based on the way you look…. is a pretty lost cause unless you’re in the league of Denzel Washington or Brad Pitt or on the small chance that she has a very specific type and you just happen to be her type.

Because there are sooooo many other factors beyond and sometimes even greater than looks that plays into a woman’s “interest” in a man, it’s really pointless to try and figure out if she is interested off the bat. The most likely answer is NO she is not! Your interest in her will make her more interested in you than you trying to figure this all out, trying to avoid taking a risk.

Sometimes women are interested initially also because of looks and mystery, but a wise woman knows that she should protect her heart until a man voices his interests, so she will not show her cards.

What Every Woman Wants

Plus, EVERY woman wants a man who will work for her, fight for her, and in this day and age all that means is that the man has to take a risk and risk getting rejected.

How Your LACK of ACTION Reads to a Woman

The more time you waste, the more likely you will find yourself in the friend zone. Because many guys are afraid to make a move until the woman has made it clear that they are interested, they don’t understand how this reads to a woman. I can’t tell you how unattractive this is, and if a woman recognizes that the man is waiting for her to make the move, it just makes the guy look like a pussy, excuse my language. A coward. Do not waste your time trying to figure out if she is interested!

See, if you’re not willing to make a move without taking a risk, you’re sending the message to the woman “I only want to be with you if it’s easy.”

The longer you wait, the harder it will be for you to ask her out on a date because your casual interactions will look like you’re already “hanging out.” She will take that as you just wanting to be friendly… It might also confuse her if you take too long to make your move. She’ll be thinking, Why did you wait so long if you found me irresistible? That doesn’t add up… Plus, she’s already labeled you a buddy by that point. The longer you wait, the more your interactions will read one of the following:

      1. I’m too much of a pussy to ask you out before you make it clear that you’re into me.

      2. I’m not really that interested in you.

      3. I just want to be friends.

      4. I’m interested but not enough to do anything about it. I’m just not that into you.

      5. I’m interested but I’m also interested in other women and you’re not on the top of my list.

      6. I don’t notice you at all in that way.

      7. I’m just teasing you with my casual interactions and glances. I like getting womens’ attention to boost my ego, but I’m noncommittal and I don’t plan on making any bold moves.

Ehhhh, you do NOT want any of these to come across! I don’t want to be harsh, I just want to speak the tough truth from a loving place.

What to Do if You Already Have a Female Prospect

The only tell-tale sign you can give a woman to show her that you are interested in her romantically, is to ask her out on a “date.” Do not ask her to “hang out.” Women don’t get excited about “hanging out.” It’s the easy line guys use to avoid taking a risk. It shows that the “hanging out” can be taken as friendly or maybe more. It’s left open for interpretation (platonic or romantic?) so a guy can feel less rejected if the girl says no. If you spell it out that you want to take her on a “date,” there is no hiding behind that term. It means exactly what it is: I WANT YOU ROMANTICALLY. And that is EXACTLY the kind of message you want to send. Women don’t get dolled up to “hang out.” They get excited and dressed up for a “date.”

What to Do if You do Not Have a Female Prospect

If you are a single man and want to be in a relationship but you don’t have any prospects, first you have to stop making excuses for NOT expanding your social circle. If you’re not crushing on anyone in your social circle, it’s time to get online, go take some new classes, go to another church, or ask some friends if they know any cute girls. Make it a PRIORITY to meet some new women. Find that cute girl and then don’t waste anytime trying to figure out what she’s thinking.

Again, for you, this time calls for ACTION and DETERMINATION.

You need to start flirting with this cute girl ASAP, complimenting her and telling her she’s beautiful today…

Basically, if you’re thinking it (unless it is sexual– that’s too early) SAY it to her. Every bone in her body needs to know that you are interested in her romantically.

Tell her, ” Hey, _____, what do you like to do for fun? … Wow, sounds great…. I want to get to know you better.. over dinner? Let me take you out sometime…”

Her: “Uhhh, umm okay?

You: “Like tonight at 8?” smile! that line is flirty/funny:)

and then always end with making sure you say the word “date.”

When/if she agrees, say, “Great! It’s a date!” just to reiterate that your intentions are NOT platonic.

What if She Rejects Me?

If she says no, it doesn’t mean it’s over. Guys, this is where you have to remember DETERMINATION. Persistence my friend: “Aww, ____ why not? A free meal? Great company? I want to get to know you better. You won’t regret it, I promise.”

If she says no still…. when you see her again on another day, it’s only awkward for her and you if you act awkward.

Still keep complimenting her, flirting with her. More likely than not, she will be won over eventually if not right away.

Be an endearing “pest” every now and then to remind her you can never see her as just a friend—“How about that dinner date?”

When you compliment her and she starts looking uncomfortable, just say it out loud, “Does this make you feel uncomfortable? I’m sorry, there’s just something about you.”

Omg, be cheesy, be corny, be foolish. All these methods have won women over throughout the centuries. But whatever you do, don’t be silent about your interest in her. And don’t wait to find out if she is interested.

Instead, find out what she’s interested in (if you can’t get anything, a woman’s gotta eat! Everyone loves good food.) and do everything you can to try and convince her to go out with you on a date.

If you need a great example of a guy who gets rejected over and over and still wins over the woman, watch the movie Bad Teacher with Cameron Diaz. Don’t imitate Justin Timberlake’s part, but the other guy.

How to View Rejection

Don’t be the nice guy who wants to avoid rejection at all costs… Learn from the player/pick-up artist who knows that rejection is just a part of the process, a necessary evil. Like battle scars, badges of honor.

He doesn’t meet a woman, fall madly in love with her, banking on only her to say yes. He may be asking out numerous women or just one woman at a time, but he knows that he can’t just put all his eggs in one basket until she actually agrees to see him and actually wants to be exclusive. In his mind, one woman’s “no” propels him to think “okay… next” and he doesn’t wallow in the rejection, doesn’t try to overanalyze it. She just wasn’t into him or didn’t give him a chance. Oh well.

Gentleman in Waiting?

Notice how there’s no term “gentleman in waiting?” It’s “lady in waiting.” When you wait around, hoping that she will make it clear that she is interested before you make your move, you play the role of “gentleman in waiting” and that just makes you look like a pussy! Let women do the waiting and hoping. Guys are in the position to initiate, and when they do, even if a woman is not initially attracted to you, she will have more respect for you, and she will actually take notice. It makes women look your way. It gives them a chance to give you a chance.

Good luck!

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Article written by:

I love thinking about the intricacies of dating, love and life. I share my tiny lessons in the hope that it helps you as you navigate the dating world.

Join the discussion

  1. hunter

    …This will mostly work, when, most guys, stop approaching the 5ft. 8in., long neck, 18 inch waist, double d cup…

  2. Jeff

    My problem is less of a fear of rejection it is more a fear of accusation. If you look at the definition of sexual harassment, half of the advice here fits. I have hung out in the womens center to learn more and the things that you can get in trouble for seem innocent enough.

    How do you deal with the modern landscape where any sign of interest in women can get you in serious trouble.

  3. MidoriLei

    Jeff, you do have every reason to be wary with all the sexual harassment stuff going around.

    But last time I checked, asking a woman out on a date is not sexual harassment. Talking to her dirty and giving uncomfortable sexual innuendos is sexual harassment. Trying to touch her when you haven’t been given the go is sexual harassment.

    There is a way to ask out a woman without it looking like you’re making sexual advances. Of course you do have to be more cautious in a work environment.

    It’s always advisable to state up front, “hey I hope this doesn’t seem too forward or make you uncomfortable, but I’d love to take you out on a date sometime.” Very staight up, innocent, not sexual AT ALL.

    BUT it makes clear just by using the word “date” that it is not just a friendly invitation. It is for romance…. without spelling it out.

    I think that if you just treat a woman like a gentleman you don’t have to worry about any sexual harassment issues coming up.

  4. David

    Haha. I like the part about No ‘gentlemen in waiting’. That’s a good one.
    There is also the thing about expanding your social circle, and I was wondering if there are places where that isn’t really appropriate.

    For example, you mention church, but I have always thought that using a house of god as a meat market when you are suppose to be there to worship god, is sort of tacky. I have seen it more than once, were there will be a person going to church primarily for that reason, instead of what church was intended for.

    Then on the other side of the coin, there are people who think its not right to date a co-worker. At first I used to think this was just an issue with maybe a few employers, but I have actually heard this more from employees. Personally, I don’t see anything wrong with establishing a relationship with someone you like at work, as long as you still do your job, but appparently there are some that do.

    So what do you think? Are there places where pursuing someone is innapropriate, or is any place fair game?

    • MidoriLei

      Hi David,

      You make some valid points. I think that as long as a guy is already going to church and will continue to go to church after he meets a woman, then he’s not “using it as a meat market.” If on the other hand he only goes there for that purpose and then doesn’t continue to go there afterward, then he is “using it as a meat market.” In the bible it says that “A man who finds a wife, finds a good thing and gains favor from the Lord.” (proverbs 18:22)

      God definitely wants a man to “find” a woman, and by find, I mean go out there and look for her. And what better place to find a woman of God than the house of God? Worshiping God is not limited to singing songs to him and listening to a sermon. Worship involves a life of choosing God as “Lord” and doing what he commands. In a way, even sex in marriage is a form of worship to God because it is doing what God commands, (he commanded Adam and Eve to be “fruitful and multiply.”) marriage, family, kids, sex, all these things were God’s invention and something he blesses and wants to happen…

      And for all of this to happen, it’s going to require a man to “find a wife.” I don’t see any reason why it would be bad to look for a woman in church.

      As far as work relationships, I think that it’s fine as long as it’s fine with an employer and as long as you can continue to work well if you split up. If it will cause you to need to find another job because it will be too awkward working after a breakup, then you just have to ask yourself if it’s worth the risk.

      I think any place is fair game.

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