Why Did We All Date Losers in Our Twenties?

For this current Millenial generation, there is now a new phase of life most young women will experience.  There is adolescence, then college, then there is dating losers, till finally we reach adulthood.  I know some of the most accomplished, beautiful, smart, compassionate women and yet so many of them had these starter boyfriends in their early twenties, it can’t be a fluke.  Some of them are married now, some are still single, but regardless we all seem to be asking ourselves the same question, how did we date those guys for so long?  I’m not talking about men who weren’t right for us – I’m talking about genuine losers.  Guys that were jobless and mooched off us and took us for granted and never lifted one finger for our relationship and depended on our social life and didn’t realize what they had.

Why did we put up with so much?  One friend of mine was waitressing at two different restaurants to support herself and her boyfriend so he could run the business they were starting.  This may have started out like an equal division of labor but by the time I met the two of them, she was declaring him on her income taxes and he was drinking, playing soccer with his friends, and later we found out cheating on her.  She’s a smart girl and now she’s dating a guy a thousand times more worthy of her but how did she get there?  How did I get there?  Why did we put up with these total losers? 

Another friend of mine wasn’t allowed to acknowledge their relationship publicly on facebook so no one would knew they were a couple (he also was determined later to be a cheater).  Another girl dated a wannabee actor who was so poor, she was paying for most of his food, then she finally got him a bartending job where he promptly spent all his time getting wasted at the bar with his new friends and developed an adderall addiction.  Another friend was constantly complaining about her boyfriend who she didn’t think was very smart and would publicly embarrass her by saying crass idiotic things in front of her co-workers, yet she stayed with him for four years.

And then there’s me.  I too was in love with a loser once.  Of course, at the time I didn’t think he was a loser.  I thought he had promise and was about to make it big and was cute if you looked at him from the right angle and my personal favorite: he’s just smart in a different way than I’m smart.  Once I got out of that relationship and became alerted to the coterie of men that were out there to date in comparison, I slowly realized the truth.  I too, had been dating a loser.  But that’s the thing about love.  It doesn’t just blind us to our partners.  It blinds us to what we should expect from any partner.

I know there’s a temptation to use a bit of revisionist history when analyzing past relationships that didn’t work out.  So if it were just one or two of my friends, I’d be hesitant to make this blanket statement.  But it’s true for so many women, it seems to be a legitimate phase that most women in their late twenties or thirties have gone through.  I think a lot of us girls were struggling in our own careers or even struggling to understand what we wanted out of life after college, so perhaps a lot of what now makes them a loser at the time seemed to make them struggling actors/entrepreneurs/musicians.  But now, I know where some of those guys are, and none of them seemed to have really achieved the level of success where we thought they were heading.  But many of us are now dating men who are treat us well and prioritize us and gainfully employed.  So why did we put up with it?

Perhaps, this is because many of us had our first serious relationship after college.  For the baby boomers, relationships got serious in college.  For my generation, hook-ups were serious in college.  College is not conducive to relationships.  You move in a circle of friends and most men want to play the field and there aren’t that many serious relationships around you.  So you sort of quasi-date, but for many of my friends, our first serious relationship and the first man to truly impact us emotionally, came along in our early twenties.  The first time you fall in love is monumental.  It rocks your world and shakes you to the core and you become addicted to the feelings love and intimacy provide.  So for the first time in our lives, we were in love and we kept those guys around because it’s hard to break-up with someone you still love.  Why didn’t we realize nine months into the relationship that these slackers were lame and dump them right then and there? 

Perhaps some of it was fear of being alone or a fear of not doing better.  But the fact that I personally know hundreds of women who went through this phase, it seems to me it was more generational.  Perhaps as we came out of college, also insecure about our own career plans or life decisions, we chose to be more conservative in our relationships.  We all had big dreams and big plans and were making big daring decisions that our parents had not made.  And so the one place we chose not to be daring was boyfriends.  We were brave enough to move to New York or the Phillipines, brave enough to pursue filmmaking or investigative journalism, brave enough to take assistant jobs that paid nothing and didn’t give us health insurance, brave enough to travel the world or become a ski instructor for a year while we figured it out…but we weren’t brave enough to do it alone.  At least not right away.  None of my close friends are still dating the loser guys they dated in their early twenties.  And it taught us all valuable lessons – I appreciate all the little ways my boyfriend is thoughtful now even more because I was in a relationship with someone who wasn’t nearly as thoughtful.  Every time Mr. Dreamboat takes me to dinner now, it’s not just being taken to dinner that I appreciate; I appreciate that he remembered the day before to make reservations because for years I dated someone who didn’t even care enough to make reservations on my birthday.  So can I really regret dating a loser in my early twenties?  It’s hard to say I have any regrets when I’m so happy with where I am now.  But then again, I wonder if someone had said to me a year in, wake up, you’re dating a loser and not all men are like this, if it might have saved me the headache of the next two years of my life in a relationship with a guy that was living off of his parent’s allowance. 

Tamara Shayne Kagel is a writer living in Santa Monica, CA. To find out more about her, visit” title=”@tamaraskagel.” target=”_blank”>@tamaraskagel. © Copyright 2011.