HowAboutWe: There’s Someone Out There For Everyone. Maybe.


So, my OkCupid Month of Yes has hit a little bit of a halt because I am preparing for my half marathon on Sunday [SUNDAY!]. I am trying to stay away from jazz and liquor so that I can be in tip-top shape for the race, which presents a little bit of a conundrum for going on first dates [I wish I was someone that didn’t prefer a little liquid courage, but I’m not. My therapist and I are working on it. Ha.]

Anyway, below I present to you an online-dating story from the archives. 

I joined HowAboutWe because a friend of mine had had some success with meeting quality suitors there. As is standard with these sorts of sites, you can peruse and click “I’m intrigued!” for free, but if you want to send or receive messages, you must pay a monthly fee. 

I hadn’t committed any money to the operation (I hadn’t even really filled out my profile or added a picture), but I was receiving their daily [hilarious] emails and date recommendations. One day, I opened my email to find a suggested activity with a guy I found attractive. I clicked “I’m intrigued” and waited. 


I also added a picture to my profile. You are 95% more likely to get a response when you have a picture, yadda yadda yadda [so the FAQs tell you]. I mean, I would never respond to anyone without a picture [save for during OkCupid Month of Yes], so obviously this is a requirement if you are going to actually USE these websites. However, up until that moment, I had just been window-shopping, so a picture wasn’t necessary. The picture that I added was one of me from Halloween, when I dressed up as [a blonde] Joan Holloway from Mad Men.


I received an alert that I’d gotten a message almost immediately. HowAboutWe was withholding said message from me until receipt of payment, so I scoured the internet for a code for a free week. [Listen. I’m a girl on a budget.]

When I was finally able to read his message, all it said was: Are you wearing a wedding ring?

I was, in fact, wearing a wedding ring as part of my Joan get-up. Profile picture FAIL. 

We exchanged a few messages, discovered that we had the same first name, and he asked me for my gchat handle. I was tentative to send it to him [“If he knows my gmail address, then he’ll figure out where I live and come and kill me!” Every time, that’s where my mind goes. Every. Time.] 

He immediately messaged me on The G. He revealed to me that he was not actually located in New York. He lived in San Francisco. I was perplexed because HowAboutWe only sends you local dates. Why did he appear in my inbox? I eventually came to understand that, apparently, he had been in New York on business and changed his location. He was now back on the West Coast. Interesting. 

Since I am from the West Coast and was going to be heading out there in a few weeks, it didn’t seem like such a lost cause. 

We engaged in some casual small-talk [like you do on your very first gchat conversation], and then he had to leave for lunch. But just before signing off:

Him: And by the way.
If we like one another when we meet we have to have sex.
Like has to be done.
I have never hooked up with someone with my name.
How awesome would that be!

Thus began a string of gchat conversations wherein he revealed his crazy fantasies and fetishes to me, and I blushed and sent a demure “haha” in return. 

Eventually, he confided his ultimate goal for our same-name-tryst: “I would love to watch my girlfriend fuck the hell out of a big dick. Right in front of me. Then throw him out when she was done and cuddle me and say sexy things to me. And sweet things.”

You guys.

This is why the internet was created.

People can find someone to fulfill their cuckolding fantasies. Sadly for my same-named friend, I was not the gal for that position. We never met.