Self-sabotage is never limited to just one part of your life

At the start of our road trip to his cousin’s wedding in Illinois, the farmer says, “I have a present for you.”

He pulls out a book that is wrapped in the paper that wrapped the last present I got him: Lolita. Which he reads every time he sleeps over at my house. I knew that he would be too embarrassed to buy it himself because he is still unsure whether it is literature or porn.

He is a good gift giver. It is a romance novel: The Rancher and the Rich Girl, by Heather MacAllister.

“I found it at the library,” he says. “The story is exactly like our story.”

It’s true. The rancher does not want to be romantically involved with the woman, but he is great with her kid, and she wants to use her money to make the rancher do what she wants. Even the riding around the farm together, with her holding him too closely.

I like her immediately, and I start skimming the book, but then I am frustrated: “Where’s the sex?”

“Page 165.”

I read it to the farmer while he drives. Then I read our future aloud, ” ‘Matt was looking around his kitchen at the new refrigerator, dishwasher, and stove.’ ”

The farmer is quiet. It is serious business when I start talking about remodeling his kitchen. Which I talk about all the time.

We drive for a while without talking. Then we stop off at the hotel to change. We are running late, but there is enough time for me to give him the sort of kiss that lets him know that I will try not to say things that bug him. I will try just to have a fun night. He seems happy. Like there’s hope for the evening.

At the service, guests look more like city people than I expected, and I get sort of upset that I let the farmer choose my dress because it’s a little bit too prim for the crowd. But then I realize that the spaghetti strap dresses are not on the farmer’s side of the wedding. The first guy to start a conversation with the farmer is his uncle: “Did you start harvest?”

“No.”

“Everything’s late. Illinois is, too.”

Harvest is a waiting game. All the farmers wait around to see who will cut the corn first. You want to wait long enough so that you don’t have to spend money drying the corn with expensive propane. But you don’t want to wait so long that the stalks start to keel over. This reminds me of working with venture capitalists. They want to invest, but they want to wait until we are almost out of money. And they can’t stop talking about it. The venture capitalists and the farmers would love each other, if they could just agree on a place to meet.

The farmer’s family gathers on the side, and each person asks me where I’m from. I am feeling so good about the farmer that I say Madison. Usually, saying I’m from Madison gives me a rash. Not a visible one, but maybe like a brain rash or something. So usually I say I’m from New York City.

(Side note: This is a good lesson in resume writing here, really. Because this is not a lie but not the first truth that comes to mind, but I always feel like it makes me look good, which is how you should look at a resume.

The farmer, by the way, thinks that it’s a lie. He thinks I should say I’m from Wilmette. Which is the town I grew up in and haven’t lived in in 25 years, and the last time I was there I wasn’t even living in a house but in a mental ward because I was so insanely bulimic. But he still thinks Wilmette is the right answer.

I ignore that. I am the resume expert, after all.)

There is an hour between the ceremony and the reception. We drive around. And walk in parking lots. It is largely romantic because we are both dressed up and we look cute together, even though he picked both our outfits. He actually has a knack for fashion and I wonder where he could possibly get it.

After a while of walking around, we can usually get to friction. Frequently we torture each other about religion. He asks me if Anne Frank died. “I can’t remember,” he says. I tell him that Baroque church art shows St. Teresa having an orgasm. I say, “I think God went down on her.” (That is an example where he is not intentionally annoying me, but I am intentionally annoying him. If we break up, and readers want to blame me for the whole thing, they can refer back to this moment.)

At the reception, the farmer’s extended family is fun. They talk about cities like Peru and Sandwich like everyone knows where they are, and I ask the stuff I’ve been dying to ask but have never had the proper audience. For example, I ask a cousin if the farmer’s sisters hate him: “Why don’t they ever visit?” I ask. The family hates conflict, and my friction-frought conversation gets me nowhere. Well, I do get more blog readers. Because the natural response to someone thinking I’m a lunatic is, “How did you two meet?”

The night in the hotel room is fun, once I stop feeling like I’m at work, since half my work life is spent at hotels. We start to have sex but then he checks his calendar. He keeps track of my cycle in the same spot he keeps track of the cycles for the pigs. And I’m ovulating.

I roll over to his side of the bed and open my mouth to talk about condoms, but all that comes out is, “I think I’m going to die from the stress of funding my company.”

Were you thinking that maybe I am fun to date? Surely this has changed your mind.

I give him back his underwear while I look for mine at the end of the bed. I can usually stay confident about getting funding and keeping the company on track, but now, not checking my Blackberry for ten hours (well, sort of not checking) has left an empty spot in my brain where doubt seeped in. “I am doubting,” I say.

The farmer is surprisingly supportive. He is not the supportive type. I could write about my take on the origin of this deficit, but I’m sure his family reads the blog. So let me just say that he really came through, and then, when I had my guard down, he said, “Why didn’t you get funding when you were not so close to running out?”

This is, of course, a logical question from a man who runs a small business with the cash flow equivalent of a prep-school student on spring break. The farmer is good with money. He could make his farm work on any amount of money.

And this is my problem in life, I think. I have something good. Like a company that is on fire, or a relationship that is on fire, and I do something to mess it up. Not really really mess it up. But mess it up just a little. Like, maybe something is wrong with me that I can’t have things just going well.

But we end up having a truly romantic night where I am even being vulnerable—difficult for me—and the farmer is making me feel like I can conquer the world. Or at least fund our next payroll.

And then, on the drive home, I'm spoiling it again. He is holding my hand and I tell the farmer that the woman in the book got a horse. I remind the farmer that I want a horse. She got it for her son. And my son wants a horse.

The farmer does not like horses. But now he says, “Okay, maybe.”

And I say, “Great. How much is it?”

He says, “Don’t ask me about the horse while I’m driving.”

I know this isn't going over well. So I switch to one of my favorite negotiating tactics: Silence. Sometimes if you are silent the other person will say something that gives you another opening for getting what you want.

Instead, in the silence, I think about how maybe I should just drop it. Maybe I should practice now, seeing that I have a chance to have a nice drive home with a nice guy. I should take that and not mess it up. And then maybe, if I practice this for a while, then when investors tell me again that I have a great company that is totally fundable, I won’t screw that up either.