So long, farewell, auf wiedersehen, goodbye!

Where do I begin? It has now been several months since the BBLand Dating Challenge, but this one encounter still lives fresh on my mind.

Perhaps it’s because it was the only date from the challenge, during which I felt any form of a connection, or perhaps it’s because he wooed me with his Smart Car — hey, a car is a car, and if he’s willing to travel up to Harlem for me, that’s a major win!

Regardless of why, my dates with Smart Car Boy stood out. That’s why when our two-date tryst ended (a mere 4 days after it began) I was surprised by my devastation.

It all started late on a Tuesday in March. I had just celebrated my birthday and decided that this 27th year of life would be the year that I get my ass off the couch and actually put some effort into dating and meeting new people — and that meant going on late-night weekday dates. That’s why, at 10:15pm, I strapped on my first-date boots, grabbed my keys and headed out the door to a new bar by my house.

When Smart Car Boy walked into the door, I immediately knew that I liked him. He was cute (in a nerdy kind of way), and we had great chemistry and conversation. By 12:45am, I decided that it was time to call it a night and politely suggested we end the date.

“Oh, you’re ready to go? What are you doing after this?”

Ummm… what?! It’s a work night. You think I can just stay out all night? What’s your game dude? Do you think this is a booty call?

“Ha ha nah, I have to work early tomorrow.”

“Oh, okay. Well let me grab the check.”

And with that we parted ways with a polite hug goodbye. But of course, that wasn’t the end. As soon as I got home I sent him a text, thanking him for the drinks and letting him know that I had a “nice time” — to which he responded “I’m glad you had a nice time.”

In my 27 years on this earth, I have always prided myself on being able to text with boys. I mean, I’m no boy-whisperer, but I have always been able to hold an intelligent texting conversations and get my point across. Well apparently, I was wrong. According to one of my best (and bro-iest) guy friends, my “I had a nice time” text signaled that I thought Smart Car Boy was boring — so not the case! His recommendation was to be more straight forward, and ask him out on a second date. And so I did.

We made plans to meet up on the following Friday. While we were supposed to grab drinks at 7, he had to push the date to 10:45pm (late again, I should have seen this red flag).

Since I wanted to see him again (and I wanted to get that second-date point), I agreed to the new meet-up time and arranged to grab dinner with some friends. As you can imagine, one margarita turned into five, and it soon came time for me to meet up with Smart Car Boy.

Date #2 was just as lovely as the first one, if not a bit drunker. We went bar hopping, he took me to some cool new digs, and ultimately we ended the night at his house. Let’s just say that I earned that second-date point, and should have earned the “third-date” point as well 😉

But of course, all New York romances must come to an end. Turns out that Smart Car Boy was headed to Europe for two weeks, and once he returned, he was never to be heard from again.

But wait, you may ask, I thought you had chemistry? I thought you had potential! Yeah, so did I. But whatever, there’s far too many fish in the sea, so I’m on to catch the next!

Bossy Babe



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