My Weekly Date with a Liberal


Breitbart slowly approached the woman. This was the second time they had been together in just 3 short weeks. But in that relative blink of an eye, something had changed. Something she couldn’t put her finger on. He was different somehow.

And then he showed her.

Any questions she may have thought to ask would not have been heard above the pounding of her heart, even if she could have mustered a single breath to speak.

It was true: his Big Hollywood had grown monumentally since their first encounter…its potential size and scope immeasurable and undeniable.


It gets bigger.

_______ _______

Note: The above scene is WGA registered.

For those readers unfamiliar with my specific niche within the Big Hollywood community, I urge you to read my initial column before proceeding any further.

Consider it an army field manual of sorts. With a better understanding of my motivation and commitment to research, this manual will help you survive with me, side by side, and together, we will navigate the treacherous mine field which is the dating of a Liberal.

Note: In the case of this field manual, torture is permissible and lawful as it is self inflicted.

If you choose to continue without watching the Pilot so to speak, at least let me share with you one of the sharpest insights I’ve read on the subject.

“The divide between the sexes is great and mysterious. The divide between the sexes with opposing political perspectives could prove to be dangerous enough to cause irreparable harm to anybody willing to explore it.”

– Jon David

As a noble and anonymous crusader for Big Hollywood, I have decided to dive on the grenade for all conservatives and date One Liberal a week. The following self mandated criteria must be met weekly.

  • She has to be a confirmed liberal
  • I can not tell her I’m a conservative until mid way through the date
  • I shall report my findings honestly, and in excruciatingly painful detail.

Date #1 “Gwendolib”

Picking my first liberal proved to be more of a dilemma than I had anticipated. After all, liberals come in many different forms with gradient shades of hypocrisy accompanied by various degrees of passion with which to loathe our great country. However, once I made my choice, I knew I would approach the date with an open mind.

I recall meeting Gwendolib a few years ago at a dinner party. I was with my girlfriend at the time, who hadn’t yet found a dosage of Adderall that would keep her from regrouting an entire bathroom at 4 in the morning. Gwendolib was with her fiancé who carried a book about Falconry in his pocket at all times. Surprisingly enough, neither relationship lasted. But at that party, I recall a connection…a meeting of the eyes…an unspoken understanding between me and Gwendolib. It wasn’t political. I was hoping it was sexual. But when you’re dating someone who’s trying to level out their Adderall, you don’t even toy with the idea of infidelity, not that I would….but a boy can dream. Alas, I think the connection was a silent acknowledgement of our respective relationships coming to their inevitable and timely demise.

Cut to: early last week. I called my ex-girlfriend to see if she was still in touch with Gwendolib. It had been several years. I was careful about my inquiry; sensitive to the fact that my ex still had feelings for me. We talked of the past…the mistakes we made…how hard we tried, and that she had subsequently found out that Adderall was not the appropriate drug for her and that she was now coasting comfortably on a moderate to heavy dose of Lithium. With this revelation, I felt exonerated from any mistakes I had made in the relationship and promptly attributed all of the blame to her, which she accepted calmly. A girl once told me that if you want to make a girl like you, ask her to set you up with someone else. I was semi hoping this theory was correct and through my inquiry, our old passion would be re-ignited. As it turns out, the theory is not true and my ex promptly set me up with Gwendolib without even blinking an eye. *

* Note: I attribute this to the Lithium.

I put the past behind me. My research was the future and my future was Gwendolib.


  • Hometown – New York City
  • Education – Harvard University
  • Occupation – Artist
  • Facebook Political Views – Liberal
  • Bosom – Ample

It was time for my first date with a liberal. I had found her.

Being a traditional guy, I offered to pick her up. She seemed uncomfortable with this notion which then made me feel uncomfortable for offering and then somehow, through this exchange, I ended up feeling like Joran Van Der Sloot. This was not the vibe I was going for. We agreed to meet at the restaurant.

Note: I attribute the death of chivalry solely to the success of Greta Van Susteren.

I parked around the corner for fear she might see the “Wounded Warrior Project” sticker on the back window of my SUV. The last thing I needed her to know was that I was grateful to our troops. My cover would have been blown immediately. My research sample…soiled. So I hoofed it.

We arrived at the same time and promptly had the awkward hug moment, but being a professional journalist, I took the opportunity to confirm that my stats were correct: she did indeed have ample bosom.

I guided her to the bar where we took a seat. Although the original plan was to meet for a drink, she mentioned that she was hungry. Being a fiscal conservative, I pointed out the merits of the extensive bar menu in hopes that she might select the cheese plate or perhaps the Sliders…those trendy mini burgers that have become so popular apparently because they are small. I was hoping these options might create the illusion of an entire meal. However, being a liberal, she was big on entitlements, and opted to order off the pricier dinner menu.

I intentionally chose the day after the inauguration for my first date, as every liberal I know was changing their shorts with every Obama event that week….including the “We are One” concert which was exclusively licensed to HBO. Apparently “We” are “One” only if we have HBO. Bring us together baby. Bring us together.

I figured by the time the actor returned with her Pinot, I would be nodding, agreeing, and voicing these words: Yes. The Inauguration brought tears to my eyes. Yes. I am glad Bush is gone forever. Yes. He is the change he told me that I am waiting for….We are the change he’s been waiting for….We should stop waiting and change….whateverYes. Yes. Yes.

It was like fishing for Halibut…which incidentally I just learned that you don’t strike a halibut…you just sort of let it run with the bait. So I waited and waited. Waiting for the halibut to run so I could pick my moment at the height of hers and announce that I was a Republican. Watch her expression change from joy to disgust to anger and then I would fight. I’d fight that halibut to the bitter end, drag it up to the boat, Billy club it with facts and common sense, and then come home, gut it, cook it, and serve it up Al Mojo on Big Hollywood….on the pricier dinner menu.

But here’s the thing. The Halibut never ran.

She never brought it up. Not once. She never mentioned Obama, the inauguration, change, hope, tax hikes, socialism….nada. Now let me recap real quickly…..this is a girl living as artist in LA, raised in New York, a Liberal from Harvard, ample bosom, and she never even uttered his name the day after the inauguration. Now there are a few ways to interpret this:

  1. She hadn’t heard about the election.
  2. She was classy enough to not assume I was an Obama fan
  3. She had ample bosom.
  4. B and C

I was pretty sure the answer was D. Now this may be disappointing to some readers but I have to remind you all that I promised authentic reporting regardless of the outcome. The goal here is to learn.

And what I learned was that Gwendolib was very charming. She was flattered that I remembered her from years back, and was “pleasantly surprised” that I contacted her.

She had a great sense of humor with a hint of vulnerability sprinkled with that certain I have showered today vibe which I had not anticipated. Bottom line was…I liked her.

All of the sudden I was racked with guilt. I was a liar…a manipulator. Should I tell her the truth? That I used her? That I prejudged her? That I think Falconry is pretty cool? As I wrestled with this moral anaconda, I sensed something strange….a presence. I looked down the bar where I saw a phantom image of Breitbart, unshaven and very pissed off. He was staring at me. He whispered but I heard it: “Dig deeper Jon.” Then he swallowed 7 fingers of straight bourbon, punched the guy next to him in the face for no apparent reason, and sauntered out. He was right. I had to dig deeper.

It was at that moment, the actor brought our meal: a strawberry pecan salad for her…Sliders for me. She looked down at my plate with a half smile. Although there were only 3 mini burgers, I felt as if she wanted one, so I offered 33% of my meal to her. She declined. Gwendolib was a vegetarian. I felt a tug at the line. Breitbart who had apparently come back in for another tumbler of bourbon, whispered from the end of the bar “Let out some line.” Then he punched another guy in the face.

So I asked her a single question: Why are you a vegetarian?

And then the Halibut ran…..As I raised the slider toward my mouth, she described to me in detail, the cruel and horrific process by which cows are raised…the inhumane conditions…and their ultimate violent slaughter. I won’t bore you with the specifics, but it actually sounded kind of brutal…if you’re a cow.

I considered what she was saying. Was this enough? Was this enough for me to stand up right there and announce:

I am a Republican. I am a Carnivore. Ted Nugent kicks ass. But again, I didn’t and I’ll tell you why. Because as my eyes went from her, to the mini burger then back to her again, she smiled, winked, and said “Dig in. I’ll still kiss you.” I felt a stimulus in my package but maintained my composure.

I said “I like your leather boots. Maybe I’ll kiss you back.”

She smiled, acknowledging her own hypocrisy and my witty repartee. I felt sufficiently vindicated and sunk my teeth into the 1st of three Sliders.

I know what you’re thinking. This guy’s changing the rules as he goes along. He’s not adhering to his own mandate. Sound like anyone else?

But as I mentioned early on, liberals come in all different forms and I have the honor….the distinct privilege of writing a recurring column and such it is my responsibility to make tough choices. That being said, I felt that there was no need to declare myself a Republican, and that there was more be learned by revisiting Gwendolib in the future. Let out some more line.

Already I had learned something: I could have chemistry with a liberal. It’s pretty obvious when you see us together.

Jon David (R – L.A.) Gwendolib (D – New York/ L.A.)

Note: I walked her to the Valet. Being a liberal, she was big on entitlements. Of course, she drove a Prius, on which there was no Obama sticker to be found.


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