redo: the act of starting over again when you’re not pleased with the outcome of the initial attempt

My mom taught me two things in life: 1) never depend on a man for financial security and 2) never marry a man who cannot provide for and tend to the family. I used to think these two points were in opposition with each other. Now I understand what she was saying: relinquishing your financial security to another person is tantamount to handing over your personal independence – your power of self. The second point was made as a testament to moms: it’s a full-time job, being pregnant and raising children, and men need to step up to plate, not simply as providers but as active participants in parenting. She also said you should only marry someone who brings as much to the table as you do. Otherwise the relationship is doomed.

Over three years ago, I met the man I thought I’d marry. Dexter was everything I wasn’t and everything I needed. I was 27, he was 32. He was separated from his wife. I was living with my boyfriend at the time, too chickenshit to end it. We met at a work happy hour. I was smoking a cigarette, something I did at bars when I was drunk and bored. We started discussing the merit of hedonistic investing. He owned stock in Phillip Morris. I said I would never invest in tobacco, or any other industry that was detrimental to human lives. He laughed obnoxiously and said he loved making money off of hypocrites like me. He didn’t smoke. I finally stopped.

By the end of the happy hour, Dexter invited me to continue the evening at another bar. He was already well past the point of sobriety. A partner standing next to us interjected with a “Maybe you should go home to your wife.” He wasn’t wearing a wedding ring. He wasn’t acting like a married man. I declined and went home and called my boyfriend who was in Texas for work.

The next morning Dexter pinged me on IM: Good morning, Dollface. We started chatting. Just banter. Nothing serious. Every morning from then on, as soon as I logged into my computer, I would get a ping from him that started with: Good morning, Dollface. Finally, after week, I asked him over IM the question I’d been wanting to ask him ever since the happy hour:

What is your marital status?

You really want to know?


Ok. I’m separated. My wife left me two months ago, right before Christmas. Three months before that, my wife was pregnant and went into premature labor. I was here in DC. She was in Scottsdale. I got on plane and made it to the hospital in time to hold my 24-week old twin sons in the palms of my hands before they died.


From then on, he laid it out there for me. How his mother passed away the year before, with him going through her tax records to discover she only made $16,000 a year. How his dad left him, his mother, and his younger brother when he and his brother were just toddlers. How he grew up in a trailer park. And resented his mother for working all the time and never being able to provide the things all the other kids had. How he told his mom at the age of 6 he would become a millionaire one day. How he worked 3 jobs and gave blood plasma as often as legally possible to pay for college. How he graduated at the top of his class and landed a high-paying job. How he started and sold his first company several years later. And how became a millionaire before the age of 30.

He was a self-made man. Something I utterly admired. Everything in his life he had worked for and achieved on his own. He had earned it.

That was the beginning of our relationship. That’s the beginning of my story. I should have started with this as my first post but it scares me to put it out there because I know what’s yet to come. But I’m going to do it anyway.