Why Single Women Should Break “The Rules” From Dating Experts

Recently a friend of mine and I started talking about her feelings for her best friend. She likes him, but she feels incredibly shy telling him how she feels. She feels like he should be the one to pursue her and ask her out.

Yet, he doesn’t know that she has feelings for him.

She’s afraid of rejection, and understandably so. Any time you put yourself out there, you risk rejection. What women don’t always understand is that some men fear rejection too.

I’ve encouraged her to ask him out, or at least tell him how she feels. I believe women should pursue what they want and if what they want is a relationship or sex with someone, they should break “the rules” and go after it.You’ll never know until you try.


Telling a woman to go after a man is contrary to what most dating “experts” and relationship coaches say. A few years ago, I read the book He’s Just Not that Into You. It’s incredibly sexist and not very helpful. It’s also very condescending to women. [Although it may be a  helpful read to the women out there who always end up in toxic and abusive relationships, or to the women who “date” married men for decades hoping he’ll leave his wife.]

The sexist message of women should just sit back and let a guy do all the pursuing is everywhere though, including on Huffington Post’s site. Dating and Relationship coach Jag Carrao says women make five mistakes in dating and the first one is this:

Dating Mistake #1:  Approaching Him First.  Among all the invaluable lessons in The Rules, authors Ellen Fein and Sherrie Schneider emphasize this point as the most important. It may go against conventional dating advice, which encourages women to flirt and even strike up a conversation.  While there are always exceptions, the women I coach who are struggling with boyfriends who won’t commit or husbands who ignore them almost invariably made the first contact.  A man may date and even marry a woman who approached him first, but there will likely be consequences later on…when he approaches the girl he really wants.  This goes for online dating as well.

So if I understand Jag clearly, she thinks if a woman approaches a man first, there will be consequences later including her husband may leave her?! This is incredibly stupid advice and although I haven’t read The Rules, I now have a bone to pick with their authors. Telling women not to pursue men, not to flirt, or approach him first is childish.

I think most relationship and dating advice is incredibly old fashioned and archaic. It assumes men and women are tightly bound to traditional gender roles and we’re simply not.

I’m not a relationship coach, but I do think I’m better suited to give you advice than Jag Carrao. In fact, I think anyone is better suited to give you dating advice. She says in her article:

If you talked him first or even asked him out, you can try to restore some of the feminine mystique and you forfeited as the initiator by being a bit more elusive – a little less available, a little more mysterious.

What the…?! You can try to restore some of the feminine mystique you forfeited?

I’m sorry, but approaching a man first doesn’t mean you forfeit anything, ladies.

Encouraging women to hold back from talking to men encourages women to stick to a traditional gender role–to be docile and let things happen to her. It also encourages women to play games. In turn, men either think women are crazy and/or play games back.

Here are my Five Dating Rules Women Should Follow [And Feel Free to Break]:

  1. Relationships should be built on honesty, not games. If you have to play a game to get him or her, you may have to play games to keep him or her on a string. If you’re honest and up front with who you are and what you want, you’re more likely to get what you want out of the relationship.
  2. You should be yourself in a relationship, not what someone says you should be. If you’re the “needy/clingy” girl, you’re often criticized for being overly romantic. You’re faulted for being who you are and you’re told by dating “experts” that you’ll never get what you want unless you change. This is horse sh*t. There are men who are romantic and who like spending quality time with a girl. Perhaps there is a limited dating pool of men who like this, but statistics say you’ll meet that guy. You should be yourself and be comfortable with being yourself. You’ll be more satisfied with your relationship if you’re allowed to be who you are and you’re accepted for it. [This isn’t to say that if you have serious co-dependency issues you shouldn’t work on those. We can all use a little self-growth.]
  3. It’s okay for women to break the rules. Men like women who have confidence and these days some men like to be pursued. It shows confidence for a woman to go out of her way to talk to a man and honestly, it helps dudes out. Some men get rejected often and after awhile some shy guys give up on going out of their way to talk to women. Which  leads me to my next point:
  4. Shy guys are “keepers”. Forget the “bad boys” and the “assholes”. The keepers are the shy guys, the smart guys, the nerdy guys. These are the guys who are grateful for women who go out of their way to talk to them and ask them out. They’re respectful, interested in equality and like you for who you are.
  5. Break all the other rules. Those sexist messages that say you shouldn’t talk to a man, shouldn’t seek out a guy, shouldn’t ask a man out? Break them all. You’ll be happier for it in the long run and you’ll likely land a man who’s really into you for who you are–inside and out.