First Date Chronicles with HowAboutWe.com {Part Deux}

Last week, I told you about my new found obsession with the relatively new online dating site, HowAboutWe.com. Thanks so much for helping a sista out with the profile. I'm happy to report that I scored a date. Several, actually. Unfortunately, this busy single momma only had time to go on one of those dates. Bummer, I know.

Now remember, HowAboutWe.com is all about getting people to get offline and on dates. The easy-to-fill-in prompt goes: "How about we..." and you fill it in with your best date idea.

My idea? "How about we... take a stroll through The High Line before it gets too chilly outside to do so." My logic was that my date and I could talk a bit and get to know each other a bit... and I could scope out new cuties just in case the date turned out to be a total bust.

But it wasn't.

I managed to get through the date with no fumbles. I think.

I was running 10 minutes late and when I walked up to the corner of 14th street and 10th avenue in NYC's Meatpacking District, there he was. Smiling. He's taller than he seemed in his profile pictures. 6'2" to be exact. I should have worn heels, was the first thought I had to my barely 5'4" self. He's broader in the shoulders and slimmer in the waist than he seemed in his profile pictures. Hmmm... he's cute, was the second thought that I had to my single self.

I smiled and nodded. He smiled and waved. Very smooth greeting. This could be good.

The weather was great -- warm and sunny and perfect for a stroll through Manhattan. Our conversation was good -- we spoke about our summer activities and vacations, our interests, our day job, Facebook (it's totally taking over the world), and his family (not mine, with the exception of Aiden). He was a total gentleman the entire time and halfway through our conversation I figured he seemed... safe. He's old...er than I am. Dude's got 6 years on me. And based on his let-me-tell-you-all-the-important-details-about-myself constant shift in conversation, I figured he may be ready for an actual relationship. I'm not trying to go there just yet.

Still, I tried to keep it light. And fun. And easy-going.

Our date continued and we indulged in delicious ice cream (vanilla flavor for me, cappuccino flavor for him), then drinks (glass of Chardonnay for me and a beer for him). There was laughter. Check! There was smiling. Check! There was a little flirting. Check plus! And then there was the question... "So, what are you looking for in a relationship?" he asked. Ooh no... check minus. 

Really?! On a first date?! Sheesh!

In my humble opinion, the people who ask this question on a first date are the people who do not want to waste their time on more dates with someone who is not looking for the same things as them. How do I get out of this one gracefully? And without fumbling?

"Wow, you're just getting straight to the point, huh?" I say with a chuckle. "I was not at all expecting that question."

"I just thought we should get these questions out of the way," he says. This guy is not playing games. He seems to want to settle down. Sooner than later. Suddenly, he's not looking so cute anymore.

"This is like a job interview with Chardonnay," I quip. "Well..." I proceed to say that I am enjoying the dating process and getting to know different people. I add that once I find someone who is compatible with me and I see potential with them, I would consider dating them with a more serious purpose.

He totally ate it up.

A few days after our date, I got a call from him politely requesting if he can take me out again. So I guess I didn't fumble after all. And I guess the theory is totally true -- if a guy is interested in you, he'll call. Period.

Don't forget that HowAboutWe.com is offering ONE MONTH FREE subscription to help you get back into the online dating game. Simply select "One Month," use the code "FallDating," and get your groove back, Stella! (Please tell me that you totally get the reference.)

{Disclaimer: This post is being sponsored by HowAboutWe.com. All opinions expressed herein are my own.}