First dates can be a bit stressful for some. You put on your best face; and most try to be on their best behavior hoping to make a good impression. Then there are some out there, who could clearly care less. And, lets just say this date in particular, was a bit egregious.

It was September 2012 at a Congressional Black Caucus (CBC) event that I met this individual. At this time the election for the new president was in full throttle.  With it being election season most people attending the CBC at this time were in President Obama’s corner.

I’ll start by saying that he was attractive and nicely dressed (a man in a nice suit just really does something for me). So, when he approached me referencing my natural puff, I was willing to engage. After the evening was over, he asked me if I wanted to go grab a bite to eat, and since I home bound with nothing to do, I accepted his invitation.

Over the late night dinner, we learned that we had both grew up in the mid-west, him being from Chicago, and me being from Cincinnati. He, however, had just come to the area to work on a campaign. The conversation went a like this:

“What brought you to DC?” I inquired making small talk.

“I work for a campaign.”

Now considering that he simply said “campaign”, I thought it was weird. Most African-Americans would have jumped at the opportunity to tell someone, hell anyone, that they were working for Obama ’12. He, however, was a too ambiguous.

“So, you work for Romney.” I concluded.

He laughed. “Funny that you would suggest that. Most people assume since I’m Black that I work for Obama.”

“Well, if you worked for Obama, you would have poked out your chest and just come out and said it.”

“I guess you’re right.”

He went on to tell me that he changed to a republican in 2008 while working as a lobbyist in Chicago.

“I met some people, and it just happened that way.”

“So you became a BLACK Republican in Chicago, which is the city of Obama, in ‘08’, which was the year of Obama.” I sarcastically asked for clarity.

“I know. Crazy right.” He responded with excitement.

Although, this was shocking to me, I tried to remain open-minded.  I thought that if we kept in touch after this night, we would have some really interesting conversations during this election season.  The conversation moved to what I did for a living, (really it changed to the reasons I don’t like my job). I explained to him that I would be more satisfied if I could get my non-profit off the ground. He then started reciting bible verses and telling me how God actually has design things for me to be happy. I was thoroughly impressed at his Bible knowledge- to the point where I found it to be an attractive trait.  That’s when I began thinking that this guy may be ok, and I may be open to doing this again sometime.

The next part of the conversation reversed my previous notion…

He started with, “I have a question.”

“Shoot.” I reply.

He leaned back in his chair and asked, “May I please place my dick between your breast.”

Umm… ok… WHAT?!? When you’re on a first date and someone asks something as ludicrous as this, you just assume that someone is pulling a prank on you or you are on an episode of Punk’d.  Even most guys would think that’s a little ambitious for a first date.  It’s just something that you don’t think will come out of the person’s mouth that’s sitting across from you.  Not unless this is a previous arrangement of some sort and you both already know the deal.

After I looked down at my breast to see if they were revealed or abnormally huge, I politely replied “No.”

The silver lining is that he was up front and honest from day one! I knew exactly what he was about- aside from the fashionable suit and professional demeanor during happy hour. It just so happens, that lifestyle isn’t for me.

The worst part is that I’m forced to see him quite frequently as a news commentator.   He looks so dignified while commentating on how well he thinks his once presidential candidate is  performing now being in office (which was the appropriate pick for him given that elected official thinks it’s ok to grab women by the private parts).

My experience shows that you can never really know what to expect on a first date. You can go into it with high expectations and leave disappointed, or you can go in with low expectations and leave completely satisfied (that just not this story). But you should never let that fear of uncertainty stop you from going on another first date. Who knows, maybe your next first date will be your last (again, not this story).

Tail your craziest “Dating is” story below.