What are your feelings concerning online dating? Would you treat it like a new business, considering the interactions?

What are your feelings concerning online dating? Would you treat it like a new business, considering the interactions? –@jeehtoven

To make online dating work for you, you have to treat it as if it were almost a fulltime job. Every evening, if I was not out on a date, I was signing up for online dating services, I was sending or responding to over 20 emails a night. I was making phone calls (after “chatting” through the service sometimes people want to hear you on the phone to make sure there’s not a wife standing right there).

I became so proficient about the good and bad features that I started my own online dating service called 140love.com. Unfortunately, that venture did not work. The basic idea was that not only would you get matched to someone but you could quickly decide if you liked their personality based on their profiles as well as their tweets.

The problem with the service was that many Twitter accounts are not anonymous. Nobody wanted to sign up for a non-anonymous online dating site.

So I was online 3-4 hours a night sending out messages to profiles I liked. I spent an hour filling out the eHarmony form and only at the end they told me I wasn’t qualified (“Our research shows that people who are separated usually do not have relationships that work out.”)

I cut losses very quickly. If a conversation started that I felt was going nowhere, I stopped it. If a date happened and I sensed it was not going to work out, I cut it short and that was that. Even if I felt like things could move forward, if I didn’t think it would end in a long-term relationship, I stopped it.

I had very clear goals. I wanted to fall in love. I wanted someone to fall in love with me. I didn’t want any games where we had to pretend to not love each other while we slowly eased into it. I work pretty fast. I wasn’t a believer in “the Rules” and whenever I felt I was being sucked into that game, I would back out.

Nor did I lead anyone on. For me, there was no point in just going on dates if I knew the relationship was not going to be long-term. Everything you do in life, good or bad, has consequences. The most obvious consequence of having sex with someone you don’t want to have a long-term relationship with is that you could hurt that person’s feelings AND, that could’ve been the night you would have met the love of your life if only you had been home sending messages out.

The one thing I will say is: get used to tons of rejection. Maybe 10:1 on rejections no matter how good you are (unless you are a beautiful woman, then the ratio is probably reverse).

For me it was work. Every day sending messages. Every day trying different services. And then the actual dates. I made the mistake of arranging dinners with everyone. Claudia, who became my wife, had a better method. I met her through an online dating service.

On her profile she said she was from Buenos Aires. I wrote her a first message saying, “I always wanted to visit Brazil”.

She wrote back saying, “That’s great but Buenos Aires is in Argentina.” So I thought I blew it. But she suggested meeting for a cup of tea. I pushed for dinner. Who knew what could happen?

“No,” she  said. “Tea.” She had it right. A tea could be just fifteen minutes. A dinner is two hours and two hundred dollars (at least the way I was drinking back then it was).

And so we met for tea. And now we’re married.