Needing To Date “Challenging” Men – “Good” or “Bad” Tendency?

Posted by Delaine - November 5, 2009 - Dating & Sex, From the Dating Trenches, Longing...and Learning, Support & Girlfriends - 7 Comments

dating sex challengeWe’ve all heard the expression being thrown around in the dating realm: “He/she needs a challenge.”  Maybe it’s even something you’ve said aloud yourself.  But recent conversations I’ve shared with various girlfriends has me wondering: Do we need to thoughtfully consider what this expression really means to us, especially now that we’re starting over?  Does ‘needing a challenge’ look different in our relationships at different stages of our lives?  And is it something we need to be cautious of?

My married and longtime girlfriend Tory threw my ponderings into motion when, as I described to her the kind of man I envision being with in future (intelligent, gentle, a wonderful step-father figure etc), she tacked on: “AND he has to be a challenge.  You need that, Delaine.  You need all these other qualilties too.  BUT – he needs to be a challenge.”

I knew she was right in a way.  But I just grinned and left it alone… until it came up in conversation with Tara and Hali, our other close girlfriends who are both divorcing.  I said:  “Tory is convinced that even though I SAY I want a ‘nice’ man in my life, I ultimately need to have a challenge. ”

Tara’s response surprised me.  She said the expression had an underlying tone of anxiety to it. “It’s as if there’s no peace, no sense of completion,” she said.  “As if the relationship should keep you on your toes and be a source of stress, of ups and downs, highs and lows.  I don’t think it’s a positive way to phrase what you ultimately need. ”

My best friend Hali’s take on it was even more poignant.  “We tend to attract the same kind of men into lives over and over again, but to different degrees.  You’ve been attracted to men who were hurt, broken and liars, so chances are, some part of you will unconsciously continue to mix that into ‘the challenge’ thing – hopefully on a lesser scale, of course.”

Both of my girlfriends’ spin on this expression made me re-examine what it meant to me.  Sure, when I was younger, I liked ‘the challenge’ because I was immature and enjoyed the thrill of the chase.  And yes, I often (unconsciously) went after ‘Bad Boys’ hoping to win them, capture them, maybe even change them (usually to end up rejected and dejected).  So I wondered: Am I pursuing the same futile dynamic again today by saying I want a challenge?

I phoned Tory back – I needed clarification.  She laughed, “Oh Delaine, I didn’t mean it in a bad way.  I just meant that you are a highly intelligent person in terms of how you think and process things.  And you need a man who can meet you on that same mental/spiritual level .  If you DON’T attract a man like this, you’ll end up MANAGING a broken man in another broken relationship instead of being with someone who challenges you  to reach your potential and become a better person.  ‘Challenge’ can be meant in a positive way.”

So who’s take on ‘needing a challenge’ do I think is most suitable to me?  Well…all of them really; none is absolute.  But all this has reminded me just how important languaging is to us – how we can all think we’re talking about and feeling the same thing, when we aren’t – we’re actually responding to a rich internal world inside our head that has been framed by our past experiences and beliefs.  And I admit - up till now, when I’ve used the expression “I want a challenge”, the visual/feeling I got was similar to that of my younger days.  And to me that means one of two things:  Either I need to change that visual and the feelings it invokes or…. I need to a new expression.