Ask Her: Why Nice Guys Are Awful To Date

  • Sharebar

Dear Bailey,spotniceguy

I’m a nice guy.  I was raised to treat women with respect, be agreeable, never talk down to them, etc.  I also find I am perpetually single.  My relationships last quite a while, but I always end up getting dumped after a couple years, and it usually takes me at least a year to find another girlfriend.  Is it really true that nice guys finish last?  What am I doing wrong? 

James K. –Riverside, IA

James.  It’s true that nice guys get a bad rep, and I hate to be the bearer of bad news, but it’s not nice guys that we hate; it’s boring guys.  Guys like you are truly wonderful… as a friend.  The sad reality is most self-described nice guys are just duds. Here is why.

The Nice Guy Defined

You describe yourself as agreeable. What I hear is that when you allow women to come into your life, you agree with them about everything, and hope that these women will like you for being so agreeable.

The problem is that Mr. Agreeable never gets the girl because he’s boring. What being agreeable tells a woman is that you do not have enough self-respect to stand up for your own values. You don’t think enough of yourself to own your identity, so you become accommodating, inoffensive, and boring. You become the nice guy every girl wants as a friend, but nobody wants to date. You want to wait on her hand and foot to prove just how nice you are, and when she tells you that she can’t see you this weekend, you’ll say, “Oh, that’s OK. We’ll get together whenever you’re ready.” You don’t have a plan. You’re wishy-washy. You’re Mr. Whatever-You-Want-To-Do.


You are actually giving up control over your life to the woman you want to date, and here is the big secret: women don’t want power over a man like that. Women want a guy willing to man up. We want a leader — a great guy who will take charge and make us feel safe. We want a guy who will choose the place, take us there, and handle things your way. We want a guy who may not necessarily be argumentative, but will stimulate our mind and debate us on topics if you don’t agree with us.

This is why you hear nice guys finish last over and over again.

Don’t be tricked into thinking girls want jerks.  We don’t, but given the choice between an exciting jerk and a boring nice guy, we tend to take the jerk. This does not give you license to become an ass though.

When a nice guy tries to be a jerk, it doesn’t work because it’s not authentic. He doesn’t own his words, he doesn’t come across as an ass, just pathetic, and a woman can read right through it and know that he’s just very bad at playing games.

There is however a 3rd option that women prefer: be a great guy.

A Great Guy Defined

Women want a man who treats people well and also stands up for his own principles. We want to be with a man who will stand up to us if we are wrong. We want a man who is polite, yet takes charge of the date. A man who listens and communicates his true feelings, not mirrors our own back to us. A man who can genuinely decide if he wants to pursue a relationship, not just take what he can get.

So how do you become a great guy? Practice. You have to get out of your own way and not fear the repercussions.  Follow these steps to begin your transformation.


Without this, you might as well forget the rest of the steps, because you won’t get the girl. Realize that she wants you to take charge and sack up. Don’t slouch; pay attention when she’s talking; and put your beer on the bar between sips rather than clutching it like a life preserver. Be calm; be in charge. If you can’t convince yourself that you are confident, she won’t believe it either.

But Don’t Be Arrogant.

If you lay it on too thick and make yourself the focus (or, worse, the hero) of every story you tell, it smacks of desperation.  We call this the Napoleon complex, and even tall guys can have it.  Don’t brag.

What we like instead is self-deprecation — a guy who can laugh at himself. Make fun of yourself in the past tense. Everyone loves to bond about what dorks we were in high school. It proves that you can laugh at yourself while subtly conveying that you’ve come a long way. Just be careful not to overdo the self-deprecation, lest you fail the next step.

Don’t Be a Whiny Bitch.

It’s seriously unsexy. If you can’t get a bartender’s attention for example, don’t sigh loudly and complain about the service.  Laugh it off and ask her to give it a shot instead. And your problems at work? Leave them at work. Your job is to lighten our mood, not be a downer.

Stop Being So Considerate

Don’t be a jerk, but realize that it’s OK to make fun every now and then. Nice guys hate to offend. You don’t have to be so gushing and eager to please. Poke fun at her girly drink or her iPod playlist. You know, the way you made fun of the girls you really liked when you were in sixth grade. Again, don’t let this get out of control or you get lumped into the asshole or arrogant status, and that’s no good either.


Women love compliments, but we’ve heard them all, so make it about something besides her appearance. I’ve had a thousand guys tell me I have amazing boobs, an amazing body, etc… and it doesn’t even register as a compliment. I just assume you’re trying to get into my pants. My best advice here is to genuinely listen to what she is saying, and then make a complimentary observation about her inner person based on what she has said. Trust me, this will get you far.  Ladies are always fascinated by a near stranger’s assessment of their character. It’s kind of like reading a horoscope. If she makes you laugh, tell her she has an amazing sense of humor. If she says something sweet, say she is a very kindhearted person. If she tells a great story, ask if you can steal it, because good stories like hers are hard to come by. I once was told I had a great sense of style, and I rode that guy all night. His compliment worked much better than “You look hot in that.”

Recruit a Wingwoman.

A truly good wingman is very hard to come by, and don’t always work as intended (You might get labeled as a “player” before you ever meet).  A wingwoman however is always the best choice. When a woman sees a guy with cool female friends, she assumes:

  1.  He’s fun to be around
  2.  He genuinely likes women
  3.  He’s not desperate
  4.  He’ll probably still respect her in the morning

If one of your guy friends has a cool wife or girlfriend, invite them both out and confide in her that you need her help — she’ll be flattered. Then let her work her magic.

Make Her Laugh.

Sharing a laugh makes her feel you two are “connecting.” In fact, it’s a far better indicator that she’ll think you are compatible than sharing a kiss. Just remember, no knock-knock jokes or movie quotes.  Funny stories are always good – recount the time you got chased down by your neighbor’s pet monkey after making monkey faces at it.

James, you have a lot of work ahead of you but don’t give up.  You already have the foundation of a great personality (It’s easier to make a nice guy confident then make an asshole nice), so remember that it’s OK to disagree, and it’s OK to take charge.  We like it.




Bailey Ryan is our resident relationship expert and senior editor. She is a syndicated columnist and the author of “Ask Her”, and has been a guest on several radio and TV broadcasts. She specializes in sexual behavior, relationship advice, and off-road jeep tech. Feel free to send any questions your heart desires to the magazine or Bailey directly, either on twitter: @chirebailey or email: