Love & Sex

How a Terrible Blind Date with a “Jeopardy!” Winner Shook My Self-Confidence

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"You're a lot fatter than I thought you'd be," he says.

The smell of perfume fills my nostrils as Timmy and I walk through the cosmetics section of Macy's.   

"So I was on this date with this conservative Republican," he says. Timmy and I are on a date. A first date. Is it cool to talk about another date? I ignore it. "And she was just so militant about it. I couldn't take it."

"Yeah, I normally stay away from people who admit to being Republican or say they have close personal relationships with Jesus," I say.

"I have a close personal relationship with Jesus and he wants to have one with you, too," Timmy says.

"Of course he does, I'm awesome, but Jesus already knows this."

Timmy stares at me. I look at him, searching for a sign that he was joking.

I was already doubtful when he suggested meeting at a mall in the suburbs. I am not a fan of shopping, but he kept insisting that he knew women love to shop. To be honest, I wanted to meet him because he said he won at Jeopardy! and I am a sucker for trivia. And he lived in Europe for a while.

We continue to circle the mall. He occasionally asks if I want to shop and I decline each time. He tells me I have great tits and I look at him and shrug.

"You know I don't mind your curves," he says.

"I am not really worried about it," I reply.

"Oh, well I thought you would be. I mean if I were with a guy like me, I would be worried that I looked good enough."

Again, I can't tell if he is joking. He doesn't look like Quasimodo, but he also does not look like a man who should utter that sentence. He stands at about six feet and he sports a sizeable paunch. His sandy blond hair reminds me of Emilio Estevez's in "The Breakfast Club" and a pair of wrap around sunglasses, complete with cord for them to dangle around his neck, emphasizes his '80s look.

When we met, I was surprised. I have seen a picture of him that was about 10 years out of date. But that surprise was quickly upstaged by another one when immediately he asked me if I wanted to have kids. I stammered something about loving my niece and let my sentence end awkwardly.

"You know, I don't think this is working out," I say.

"No, you know what? We just need to get a drink and sit down and talk," he says.

He suggests Applebee's. Also, not a restaurant I'd choose, but I figure I could use a drink. We settle into a booth and a waitress brings us oversized beers and he orders an appetizer.  

He starts again, asking me what music I like and I mention Arcade Fire, the Avett Brothers, and a few other bands.  

"So indie hipster shit," he says.

"Well, um, I guess."

I chug my beer and then say again, "I'm really sorry I don't think this is working."

"To be honest, you're a lot fatter than I thought you would be," he responds while shoveling something called Wonton Tacos into his mouth. His tone is so matter-of-fact, as if this is the only logical way to respond to my comment.

Tears spring to my eyes, but I don't want to cry in front of him, so I rush to the bathroom. I furiously start texting my sister. As I sniffle in the stall, I think about this guy with his feathered hair and pronounced beer gut and I wonder where he gets off commenting on my looks.

The sniffles turn into sobs and I fear the waitress fixing her makeup will send for help. I can't believe a 35-year-old man who lives with his parents and introduces himself as "Timmy" can shred my self-esteem with a sentence. I start justifying my looks. Sure, you've gained some weight, but you did just experience a messy divorce and it happens. I leave the stall, drying my tears, and examine myself in the mirror. You're not fat. Maybe there are a few areas to work on. And I stop my pep talk. Why should I care what he thinks about me?

The more I think about it, the madder I get.

Here is the problem: He drove me from my car to the mall. So I go back to the table and watch Timmy shove deep-fried disasters into his mouth, while I ask for the check (which I end up paying).

This is not my first bad date and it probably won't be the last. One man revealed he had a felony arrest record and used to drink a fifth of Jack and drive to the neighboring state. Another guy spoke endlessly about the sex addiction group therapy he attends weekly to learn more about himself "as a partner." (I said eight words during the date, so I'm guessing he actually learned little.) And there was the former day trader who now writes poetry in his parent's basement. He wasn't interested in me but hoped I'd read his work. Another guy boasted of his IQ being above 160 to which I said, "That's the geek equivalent of saying you have a big dick." His response: "My dick is big." Later, he asked me to rate the date on a scale from one to ten. I declined. I figured guys with IQs of 160 don't like learning dates with them are less than 50 percent fun.

But most of these awkward dates lead to funny happy-hour stories, not tears. And when I thought this date with Timmy was as bad as it could get, it got worse.

As we drive to my car, he begins screaming.

"You're a fucking bitch for forcing me out of my house. I have OCD and hate public places," he yells as his face reddens and gobs of spit fly from his mouth. "This was really hard for me."

As his voice becomes louder, I look at the door to see if it is locked. I might need to jump out of the car. I will laugh at this one day, I tell myself.
"You know not every date works out," I say. "That's why you go on dates to see if you can be with someone." In my head, I scold myself for talking. Why provoke him?
"I know who I should be with, my ex-girlfriend, but she doesn't want to be with me," he says. "I'm going to go to her house after I drop you off."

"Um, okay." I feel relieved. But again my conscious nudges me.

"You probably shouldn't go to her house," I say. Why I keep saying anything to this unbalanced man boggles my mind.

"And you know what? I am not 35. I'm 40. You'd probably never go out with someone as old as me," he screams.

Finally, we get to my car.

"Well, goodbye," he says. "I know we will never talk to each other again. I know we won't be friends. I hope you have a nice life."

I'm actually afraid he will try to run me down in his teal Pontiac, so I jog to my car and wait for 10 minutes, hoping he did, in fact, drive off and won't follow me.

Later, I call my sister and we review him. He enjoyed reading and was well-traveled, which also makes him seem like a confident, well-adjusted man. While he admitted to being close to his parents, I thought that showed emotional maturity, not realizing it was code for "I live with my parents."     

As much as we belittle Timmy, I let his fat girl comments affect me. I hate admitting it; he found my deepest insecurities and exploited them. One sentence and a horrific car ride set me back.

My sister assures me that the problem is Timmy not me. He's obviously crazy, she says.

For weeks, I avoid eye contact with attractive men and ignore messages on dating sites. I believe that if I interact with a guy he'll bring up my shortcomings, which I am neurotically cataloguing.

Every day after getting out of the shower, I stand in front of the mirror, examining my body. I pull at my skin, deciding what is muscle and what is fat. I conclude that my large bust makes me look heavier than I really am. I have a round face, which gives the illusion of being fatter. A thousand neurotic judgments into my appearance, none of them wholly true.

I consider taking a permanent break from the dating scene and joining the nunnery, but I realize that Timmy is an outlier. And, I become smarter about dating. Instead of making a mad dash to find someone to fill a space, I decide I'm going to find someone who is more than a few cool details. Healing from my breakup doesn't mean I need to be with just anyone. And, I set boundaries. If I don't want to meet in the suburbs because I live in the city, I don't. I have no intentions of moving to the suburbs and he likely lives out there because he doesn't want to be a city dweller.

Armed with these new revelations, I agree to meet someone at a bar blocks from my house. As I walk there, I feel a wave of nausea. What if he calls me ugly or yells, I wonder, as I start to panic. But then I stop myself. There is no way I will ever have such a terrible date again. And—just like I told myself I would during those terrible, painful moments with Timmy in the car—I laugh.