Dear OkCupid Guy: Chin up


janeJane Chung Co-founder of Klooff

One morning I received a message from guy from OkCupid:


Currently driving across the country looking for a place to put my roots down and looking for work. I've driven 6000 miles so far.

I'm looking for some specific qualities: #1: Social boundaries with members of the opposite sex #2: Religious integrity

#3: Attraction and compatibility

Anyway...You fulfill these qualities.

You seem intelligent and I love that. Would like to meet? I would. My only reservation I think is, "is she going to put a lot of pressure on me?" and I don't do well with a lot of pressure. I put a lot of pressure on myself. My efforts are often internal and I don't tolerate someone 'cracking the whip' with me... that is to say I have a low tolerance for manipulation...

I hesitate contacting you mostly because of where I am in my career. If you want to know more just ask.

“Too much pressure”? “Cracking the whip”? Who WAS this guy? A bit appalled and slightly annoyed by how he clueless he was, I ignored it. A few hours later, I received another message from him:


Could you help me out? I've had a profile on this site for a number of months. The only women I attract are crazy or overweight women. Honestly. So what is it about my profile?

Is it that I'm not 6'2"... that I don't lie to myself about my height?

Is it that I'm not yet making 600k/year? I could be an unmotivated deadbeat perpetually unemployed. I'm not, does my profile suggest that?

Is it my pictures? I am attractive. I know my pictures don't convey how I really look in person. I'm an introvert and I don't pose for pictures and stuff like that. But is it my pictures? Should I pay a professional to capture how I really am?

I would honestly like to know. I'm getting quite frustrated. I have experience and know that I'm not going to date someone who drinks a lot, smokes pot, believes in aliens or something new-agey, doesn't have faith in anything, doesn't practice that faith with action, time and effort, has liberal boundaries with men, is on anti-depressants, etc.... And damnit, I would like to date someone slim.

For a split second, I had compassion for the guy. He sounded so desperate. What if he went around having the wrong idea why women didn’t want to date him? And then it occurred to me that his issues and insecurities stemmed from what society and culture has shaped us to believe about gender roles: Women value men with money and status, and men value women with looks. While studies and statistics conclude that such stereotypes are valid, that stereotype didn’t hold true for me when choosing mates. I know I’m not alone on this issue. I know plenty of my friends who are gorgeous, smart, quality women who don’t go for men because of their accomplishments or lack thereof, and vice versa for men.

In fact, my personal experience has actually found that men of such power, stature, and wealth are often susceptible to feeling invincible of consequences when it comes to committed relationships. They’re only available when they feel like being available, which goes against the selfless nature of healthy relationships. And with many women at their disposal, it gives an illusion that there are “better options out there” which impedes from getting to know really know someone–the ugly and beautiful parts and all.

I didn’t want him to interpret my silence to contribute to his wrong assumptions. I had to clarify, and at the very least, shed some light onto his blind spot:


Hi there,

First of all, thanks so much for contacting me. I'm very flattered, and it seems like you’re on a life-changing road trip.

I'm sorry that you are feeling frustrated, and from the amount that you invested in writing to me, I can offer you why I didn't respond.

It wasn't the fact that you don't make money or the fact that you are between jobs. I would suggest, don't start with, "I would hesitate to contact you bc I don't make money...I don't have a job, etc..." Be proud that you're on a life journey and be bold in who you are, with or without your identity on those things. Good, quality women will see that.

Here is some feedback: I was off-put when you wrote, "I don't tolerate someone 'cracking the whip' with me... that is to say I have a low tolerance for manipulation..." after you write that you think I'm going "put a lot of pressure on me." It felt negative to me that you assumed those things about me. I appreciate honesty, but believe in positive communication packaged with tactfulness.

To the ones I respond to, I look for qualities that feel selfless, generous, and thoughtful. They are often thoughtful messages that tell a little about themselves and inquire about me. Then they ask if I'd like to meet up. If I do accept, they ask me which neighborhood I'm coming from and when I'm available. Once I tell them, they pick a time, place, and confirm before we meet.

Hope that helps and good luck with your search. Don't be discouraged--if it was so easy than it wouldn't be as gratifying when we finally meet 'the one.' ;)


My dad used to give me advice on choosing men, and the more I date, I realize his advice is wise.

He told me when choosing a man he should:

  1. Have a sense of responsibility. Takes ownership of his actions and consequences.

  2. Keep his word. If he says he’s going to do something, he does.

  3. Show up on time.  He respects his time and other people’s time. He plans.

  4. Do the right thing. Doesn’t cut corners and has integrity even when no one is watching.

  5. Not be lazy. Works hard but also knows how to enjoy life.

  6. Stays away from vices (women, drugs, etc). A man should know his weaknesses and not put himself in tempting situations that can harm his loved ones.

  7. Knows how and when to compromise. Both people will have strengths and weaknesses. Both people will have different thoughts and opinions. Knowing how to navigate it is key.

  8. Love his woman. Communicate it in actions, words, affection, time, and money.

Sure, it doesn’t hurt if the person you date is a supermodel or earns a gazillion dollars. But the wiser and smarter I grow, the more I look for someone who has these qualities, and realize it’s more rare and far between.