“Why the hell would I do that?”
“Because I’m daring you.”
“Ok, I love you.”
Jessica stared at the ceiling; Derek wondered how he could take the condom off without ruining the mood. They only met two hours earlier. Since then, they had shared six beers, a plate of nachos and a slightly drunk sex session.
Years later, neither Jessica nor Derek would remember who had dared whom in this conversation. What they did each remember, however, was that neither had meant it.
For a first dare on a first date, they had started out pretty big. After this, they took a step back. The next few dares were pretty small.
“I dare you to buy me roses.”
“I dare you to run around the mall shouting ‘Down with capitalism!’”
“I dare you to grab my breasts in front of that nun.”
Jessica’s previous relationship had ended seven months earlier when her then-fiancée had told her he was so very tired of her conversation. He’d wanted her to dye her hair blonde and, frankly, “sexy-up” her clothing. Right then and there she’d put on her leather jacket and left, pounding the stairs in her Doc Martens on the way down.
“Screw you,” he texted her later, “not everything we do has to be meaningful.”
He went on to date a younger woman who, six months later, dumped him because he was “old and boring.” Jessica was satisfied and had closure when she’d heard this.
The longer Jessica and Derek were together, the more the dares escalated.
“I dare you to get a small tattoo of a shrimp.”
“I dare you to buy six rainbow trout and hide each one in a different store.”
“I dare you to cancel your cable and give me all the money you save for three months.”
For some reason, this last dare freaked Derek out. Not only was Jessica weirder than he’d imagined, this challenge reminded him of his ex-wife. They’d only been married a few months but the possessive, power-crazed arguments had begun even before they’d gotten back from their honeymoon. Derek had no intention of getting dragged back into a relationship where he would let someone mess with his mind.
Mind you, Derek thought to himself, two can play at that game.
After two months of no communication, Jessica was surprised to receive a letter from Derek.
Here’s the money for the cable. I dare you to call me twice a day for a week (I won’t answer) and leave messages saying you’re sorry. On the seventh day, park your car across the street from my house and sit there for an hour with binoculars looking at my living room window.
After the week of phone calls, Derek was sitting in his car, diagonally across from Jessica as she watched his house. It felt good inside to know she was peering through the binoculars at a room he wasn’t even in. Exactly 60 minutes later, he watched her drive away. He knew he’d upped the ante and felt proud of himself. Derek was excited to see what Jessica had in store for him.
I dare you to go to your usual bar every night for a week and drink four martinis. You are to approach one stranger a night and tell him/her how much you loved me and how you foolishly lost me because of your ignorant behavior. If you see me there, I will be with friends having a good time. You are not to disturb me. You will not be having a good time.
Being a man who liked to feel in control, Derek rarely drank. On the first night, he sat next to a man with a weathered face and white moustache.
“I just lost this girl…”
“Don’t talk to me about women!”
“But she was so special…”
“My wife just left me you’re talking about some girlfriend. Don’t talk to me about women!”
The man told Derek all about his ex-wife and Derek grew restless. He saw Jessica with friends by the window. She didn’t make eye contact. He looked away.
The second night, Derek busted out his best moves on a woman with dyed blue hair. He could tell he was getting somewhere and felt sure Jessica’s eyes were burning the back of his neck.
“I’m sorry,” Derek sobbed to the woman with blue hair, “I’m so sorry.” For the first time in his life, Derek feigned tears. “I haven’t done this in so long. I don’t think I’m ready yet. I lost her! I lost her! You’re so wonderful, but I don’t think I’m ready to do anything yet.”
“It’s okay,” she said, “it takes time to heal. I’m so sorry for your loss.” She looked at him as if he were a rescued puppy.
After the blue-haired woman left, Derek drank two more martinis, went home and throw up. By the seventh night, Derek was gray-faced and knew all the bartenders’ names.
I dare you to come out with me on a date. I will make it very awkward. We’ll watch a terrible movie, eat at a horrible chain restaurant and then have a fumbling, embarrassing kiss on the doorstep to your apartment before I leave. I will mumble something about not being ready yet. You will wonder what happened.
I dare you to introduce me to your parents. I’ll tell them I converted you from being gay, that I’m deeply religious and don’t believe in sex before marriage.
I dare you to invite me to your sister’s wedding. I will get very drunk and will embarrass you. As we leave, I will ask you to marry me.
Married life was uneventful. After a few months, their dares became timid and gradually fell into a pattern of normalcy.
“I dare you to put the toilet seat down.”
“I dare you to do the dishes.”
“I dare you to stay awake for five minutes after we’ve had sex.”
This went on for some months until Derek found a post-it stuck to the steering wheel of his car.
This is boring me. I dare you to rear-end a Lexus.
Derek did as he was dared, but barely tapped the bumper. He was worried about the money and his insurance going up. Even so, this was just the kick they needed to get them out of their rut. One night in bed, after she’d fallen asleep, Derek texted Jessica.
“I dare you to let an obviously sick child cough on your hands and then for you to lick your hands.”
Jessica had flu for a week.
She texted him back. “I dare you to eat the chicken at the back of the fridge that’s been there for two weeks.”
Derek had the worst diarrhea of his life.
Each enjoyed how happy they felt seeing the other miserable and ill.
“I dare you to just fuck off and leave me alone.”
“I dare you to leave.”
As they’d been married less than five years, the divorce was simple. They each kept what they’d gone into the marriage with. Derek found a new apartment, but the texts continued.
“I dare you to never be able to be with another woman without thinking about how much you loved me.”
“I dare you to spy on me with my new girlfriend and see how much she wants me.”
Jessica and Derek never failed to do what the other asked.
“I dare you to be single for the next five years.”
“I dare you never to have children.” (Even though it tore her up inside, Jessica followed even this dare.)
“I dare you to have two wives simultaneously.” (It took several years for Derek to extricate himself from the legal and financial fallout from this one).
“I dare you never to be happy.”
Their wishes came true.
Jessica now lives alone by the sea. Her hair is gray. She owns a bed, a table and a chair. Five years earlier Derek had dared her to sell all her other possessions. In return, she’d dared him to gift his retirement fund to charity. They both faced another cold, lonely winter and an uncertain future.
I dare you to end this.
Jessica closed the card up, put it back in the envelope and wrote “Not at this address, return to sender” after scribbling out her address. Then she wrote on the back, in a tired hand, “Double dare.”