Envisioning a Date With Each of the Presidential Candidates

Ruth Fremson/Pool/Bloomberg/Getty Images

Now that the all-important Iowa caucus has come and gone, it's time for the candidates to court the rest of us. And you know what? Presidential hopefuls ought to push harder than ever before. I want to see these candidates put a little extra something into their wooing routine if they expect me to pay attention.

The parties are much like the two preeminent dating apps. On the Democratic side, you've got Bumble. The message is a little more streamlined and organized, and the whole thing is essentially set up to be controlled by women. On the Republican side, you've got Tinder. It's a (secretly more fun) flaming-hot mess with a bunch of dudes (and one intensely forward lady) bragging about themselves, flexing for the camera, and aggressively sending their junk to you.

OK, they really want my vote? Since we met on a dating app, they had to take me out before I’d even think of putting out. Wine me, dine me, and who knows... maybe one of them could get lucky.

Jeb! Bush 

Poor Jeb. We actually didn’t meet on Tinder -- he used a desperate dinner invite to get my attention and, lucky for him, I'm a sucker for lost causes. Once we got to the place, he wouldn't stop talking about how cool his dad and big brother are and how he should win the nomination, "because, you know." 

When I got up to use the restroom to consider how to cut and run, sure enough, I bumped into Papa Bush and W., who gave Jeb a ride to the restaurant. We all stood together for a moment, shaking our heads as we watched Jeb give himself a pep talk at the table -- complete with his own round of applause.

Marco Rubio

Things with Marco actually started off well. He’s young and seems energetic, he's a minority and the son of immigrant parents, he's had a relatively short stint in the Senate... remind you of anyone? But once he stood up to grab our drinks from the bar, there they were: the boots. I just can’t do the boots. I'm sorry, Marco. 

See? I didn't even mention how he sucked down all the water even once.

Jim Gilmore

Wait, who?

Oh, that’s the guy with the Tinder profile without a picture I accidentally speed-swiped right on. Did anyone even know if he really existed before he sent me that upside-down smiley face emoji opener? Unmatch.

John Kasich

He came well recommended -- we have a mutual friend from back home in Ohio. As we sat at the table and he droned on and on, looking like my most boring college professor, I felt my eyes getting heavier, and heavier... and soon enough I was face first in my salad. I literally fell asleep from how boring John Kasich was.

Once I woke up and made it home, I called my friend out on his bad endorsement. His response: "Hey now, I never said he was really great, or really even good -- he's just the least-bad choice you're probably going to get to take you out." 

Ben Carson

I never thought it could happen, but I guess after my date with Kasich, karma was coming after me with a vengeance. That’s right: about 20 minutes into the date with Ben Carson, after warning me about his hot-tempered bad-boy streak and pausing mid-sentence, the good doctor fell asleep sitting up. 

I just got up and left. For all I know, he’s still there, dreaming about the days when he was the second-most popular of his group of friends.

Carly Fiorina

I actually skipped out on this date after she told me what her idea of role-playing entails. I don’t really get turned on by bringing kids into the equation.

Chris Christie 

Chris and I actually had a great time. He's a real people person. We gabbed and ate spaghetti, then he ate more spaghetti. And... more. He talked about how much he loves Springsteen and how "you know what, Obama is kind of an OK guy in my book." 

Then, something snapped. He started babbling about deporting anyone and everyone and bombing the entire Middle East, no questions asked. I was confused at his sudden change -- until I felt a leering presence hovering behind me. 

Ted Cruz showed up and crashed the date. 

Ted Cruz

With a quick bridge into a new conversation, Cruz immediately set the tone for our time together. He knew what he wanted to talk about and he didn't care whether I liked it or not, but I was going to sit through it and bear it. I was a dining-room table hostage. 

The worst part about the whole thing was having to look at his smug face the entire time. No, wait, it was having to listen to his smug voice the entire time. Wait, actually, it was all of the smug things he kept saying the entire time -- but at one point I'm fairly certain he was just recapping the new Star Wars movie and talking about Dr. Seuss, so I had to give him some points there. Too bad he never let me talk.

Bernie Sanders  

After my brush with Cruz, I decided I needed to take a swing across the aisle so I could experiment with a little of the old blue. So I finally got in touch with Bernie Sanders via his landline rotary phone and let him take me out somewhere nice and cozy -- and cheap.

You know how this one went. First, he knocked over his soup (of course the 74-year-old ordered soup) with a sweeping hand that was totally unnecessary to emphasize his point because he was yelling so loud. Bernie proceeded to rant about the evils of Big Soup for 10 minutes. When the check came, he demanded the senior discount... and that we split the check down the middle. 

Hillary Clinton

I didn't really have a choice on this one. When you go out with Hillary, you see, you're not dating her. She’s dating you. She started the night off with a few robotic smiles -- and a strange effort to agree with everything I said. No matter what I told her, in fact, she had an identifiable story with which to relate. 

But she could tell I was getting bored and saw her window closing -- so she flipped. Before I finished my pasta, she'd asked for the check, ordered me into the car, and taken me straight back to her place.

I'm just relieved this wasn’t 2020 Hillary. At that point, she'll be so desperate that she'll skip straight to the payoff: having her way with you without any courtship or questions asked. 

Donald Trump

Hillary was overwhelming. I took some time off the dating game and thought about calling up Rand Paul or even Martin O’Malley if I ever got really desperate. I didn't.

Instead, I got curious. I knew it was dumb, and probably something that could sink me for the next 30 years -- but I had to do it. I had to know.

So I went out with The Donald. Sure, from the minute we sat down to dinner he was heckled. Of course he spent the whole date talking about himself, getting distracted when catching his reflection on mirrored surfaces, and tweeting. But I forgave those flaws.

I'd heard all of his major points before, so nothing was new or shocking. I just needed to see the man behind the enigma. The one thing I couldn’t forgive was this: the whole time we talked, he kept coming back to one thing. And that was the fact that he was pining away for another. It's true what they say. The Donald would much rather have been on a date with his daughter.

Heartbroken after this final disappointment, I decided that no candidate would win my heart. Well, none of these jokers, at least. What was that you were saying, Michael Bloomberg?

Sign up here for our daily Thrillist email, and get your fix of the best in food/drink/fun.

Brett Williams is a writer in New York City. After all this political courtship, he's wishing he could just hang out, no-strings-attached style, with a lame duck politician like President Obama.