Nice Guy or Pushover?

Dear Gilly,

I’m tired of being the nice guy.  I’ve gone on plenty of dates and always end up being the friend and confidant rather than the boyfriend.  I keep meeting women and becoming friends with them (because they don’t feel “that way” about me) only to be their sounding board for the a**holes they end up dating.  What gives?  Why do women say they want to find a nice guy and end up dating jerks instead?

Nice No More.

Carmel Valley San Diego Community | Gillian Walker | Pushover Male

Dear Nice No More,

No woman wants to date a jerk , at least not consciously.  What you are dealing with here is Nice Guy Syndrome.  Of course we all want men who will love us, respect us and go to the ends of the earth to please us.  BUT…. and it is a huge BUT… you have to have a pair.  Of balls.  Let me explain.

When you consistently date women and end up on the friend ladder every time, you are not being too nice, you are being too easy.  We want a nice guy, but we want a nice guy who has a backbone.  When you are told you are too nice, it is code for saying you need to grow a pair.  Here is a breakdown to help you understand the difference between being nice and being a pushover.

Nice Guy 

  • Calls when he says he will call
  • Shows up on time
  • Communicates well
  • Treats you with respect
  • Opens doors, says bless you, brings flowers
  • Is available
  • Has similar interests as you
  • Not afraid to express emotion
  • Has a healthy social life outside of you


  • Calls you every hour on the hour
  • Shows up unexpected
  • Asks about your feelings constantly
  • Treats you like a baby kitten
  • Is too available
  • Is interested only in you
  • Tells you he loves you on the first date
  • Wants to move in with you after the first date

Most importantly, a nice guy knows how to play the game, whereas a pushover lays all cards on the table right away.  I know what you’re thinking.  You’re thinking, wait a minute Gilly, what about the fact that girls are always saying that they don’t want to play games?  I thought I was doing the right thing by not playing games.

Listen carefully:  There are games and there is the Game.  No one enjoys games, which are basically mental and emotional head games that immature men and women play to avoid real connection.  However, whether you are male or female, when you are dating, you are in the Game.  And this Game has rules.

Check in next week for my breakdown of The Rules of The Game.

I hope this was helpful for you.  Email me with your questions at

Shine on.


Carmel Valley San Diego Community | Gillian Sky WalkerGillian Sky Walker believes in you!  Her belief that her life’s calling is to be an inspiration and source of encouragement to as many people as possibe led her to create, where she offers personal growth and wellness videos as Shiny Gilly.  Gillian has over 15 years of counseling, teaching and speaking experience.  She is the founder of Therapeutic Trance Training and leads several trainings a year, certifying others in this method.  Her authentic and dynamic delivery makes wellness accessible and fun for everyone.  Her certifications include Certified Clinical Hypnotherapist, NLP Practitioner, Registered Yoga Teacher and Reiki Master.  Gillian spends most of her time speaking, teaching and filming.  She and her husband run Shiny Gilly Productions, filming web content for local business owners out of their home studio.  They also co-host a youtube show together where they discuss current events, interview local business owners, and answer relationship questions.  They are finishing up a book on dating advice that will be released later this year


Carmel Valley San Diego Community | RIDE Cyclery Encinitas

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