Friends in a Hopeless Place

Yesterday I had coffee with Will. My feelings before the date hit a wide spectrum from excited to intimidated. It wasn’t so much because I thought we’d click, overwhelmed from the possibility of real sparks; it was more because after reading his HowAboutWe profile I concluded that the chances he was a psychopath were not bad, but of course that was the reason I was “intrigued” to begin with.

He posted the following dates that caught my eye:

Date Option 1. How about we… go out for drinks and you can listen to me talk about my last relationship. I’ll detail how we met, the great memories we had and what led to its downfall. I’ll conclude by talking about how awful she is and why she has made me a miserable person. If time permits, you can say a few words about yourself.

Date Option 2. How about we… We make our own hot toddies at our apartments (or your parent’s house if that’s where you live) and Skype for a couple hours. That way we can continue to browse howaboutwe.com for people that we’d actually want to go on dates with AND we can improve on our multi-tasking skills.

Date Option 3. How about we… dress up, head to a park with my buddy dave who is a professional photographer and take engagement photos. We’ll then post the photos and update our facebook relationship status to “engaged” and confuse our friends who didn’t even realize we were dating anyone.

Date Option 4. How about we… Get a box of Oreos, go to times square and flip a coin to see who has to throw each one at a police officer. First one to get arrested loses and spends the night in jail.

His dates were the first that made me laugh. I was pretty sure they were jokes but they were still the most creative ones I saw on the site. I clicked “Intrigued” for the first one. He then messaged me back to try and talk me out of the date. I wouldn’t budge. He clearly had a sarcastic, albeit dark, sense of humor that I was attracted to.

I gave him my number and he called. This was the first time I’ve talked on the phone with someone prior to meeting them on a date. I know that’s typical protocol for many online daters, including Granny, but so far I’ve only dealt with men of the 21st century who stick strictly with readable communication (i.e. online messages, emails, texts, and sexts).

Our phone conversation was just as bizarre as his date suggestions. I was unsure of what was sincere and what was bullshit. He played me Rihanna’s “We Found Love” and asked me if the chorus “we found love in a hopeless place” reminded me of the online dating process. I was sold.

I knew what I was getting myself into, on his profile he answered: “For me, a first date no-no is: being serious.” And, “What I would bring to show and tell: 2 dozen mice and a lock for the door. A story you should remind me to tell you on our first date: I brought two dozen mice to show and tell and locked the door on everyone.”

We grabbed a coffee at a café in Union Square. As soon as we spotted each other neither of us knew how to react. We had an awkward introduction until I asked him to please recount the story (fictional or realistic) of his last relationship as he said he would on the website

He began to get into it, “She slept with my dad… and my mom… then my brother caught them,” he joked, but in person it was hard for him to keep up his schtick. “Okay, she’s actually a super sweet girl. We dated for six years, since high school, but neither of us were ready to get married so we broke up,” he confessed.

We both cracked up, settled down, and dropped our guards. He was clearly taking the piss out of the site but I was still amused. Now that the band-aid was peeled back on his ex, he let his theory on relationships flow. We talked about how when you’ve had a serious relationship fail at such a young age, in our society where marriage is a crumbling institution, it’s hard to let yourself seriously fall for someone again.

Now he’s basically just looking for a girl to attend all of his buddies weddings with and maybe grab a beer or two during the week. Commitment seemed to terrify him. He told me about how he likes online dating because it’s an ego-boost. He’s very self-confident and finds that he is able to dominate conversations and work on his game through online dates. He told his friend before our date, “This girl, she thinks she’s gonna win, but I’m gonna win.”

I tilted my head and gave him a look that read, “Come on, bud, we both  know whose in charge here.”

“Yeah, I think this one is a draw,” he said. Then he gave me some advice, “You’re very self-assured, I think it’s probably intimidating to the guys you’re meeting from the sites.” I know he didn’t mean it as a compliment but I chose to take it as one anyway.

We crossed into friend territory very fast. We looked around the coffee shop and decided that anyone who looked at our table would assume we had been pals for years. We were definitely like-minded people, masters of TMI. Will was more than intriguing. We were both clear on the fact that romantically we’d both slaughter each other but we as friends we’d kill it. Next time we hang we’re gonna go with date option number 4.

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4 Comments on “Friends in a Hopeless Place”

  1. helensadornmentsblog says:

    What a trip and very funny. Sounds like you had a good time.

  2. raregirl says:

    Date option 3 sounds like a great April fools joke!

  3. LaMurphy says:

    God, what’s with the men scared of self assured women?? You’d think/wish they’d like that.

  4. Amanda says:

    I’ve also been told that my confidence is intimidating to men. Is it too much to ask that a guy grow a pair and be ok with a self assured woman?

    BTW, I just started reading your site and really enjoy it.


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