Hire a Boyfriend (Dean Winchester)

The First Date

I met him through an app called HiBoy, a blend for 'Hire a Boyfriend'. It is a platform where people can rent others to be their boyfriends or girlfriends for the day. My friend Frida is a regular customer, she says it makes her feel less lonely, and she even has her favorite 'boyfriends' for hire. She says it is more like renting a friend because when the date is over, the hire is over. It is not an escort service and, under any circumstance, they are allowed to kiss you. Holding hands and hugging is the highlight of the date. And while at 32 I consider those things to be for middle-schoolers, here I am, waiting for my hired boyfriend.

The 'need' for a partner has never been present in my life. I've always been perfectly happy with hookups and one-night stands. However, when the invite for my cousin's wedding came through the mail three weeks ago, I realized that I was officially the only +25-year-old in my family without a steady relationship. This wouldn't have bothered me if it weren't for my mother's and aunt's constant questioning about kids and marriage in every family gathering I've been to since I reached 28 and remained single. So, two weeks ago, when I brought it up to Frida, she told me I could hire a boyfriend for the wedding and avoid unnecessary conversations. Back then, I thought she was kind of crazy, why spend money if I could just pick any guy and invite him? But she rebutted me with very valid cons. Why if the guy was crazy? I would have introduced him to my whole family as my boyfriend. And also, what kind of first date happens at a wedding? That would have scared any potential no-psycho bachelor.

So here I am, waiting for my date. I handpick him from a bunch of guys on the app. Most of them were fairly young, and I was not into that, so I had to filter it to +30-year-olds. The list was considerably reduced. Then I decided to pick someone handsome and masculine because if I was going to pay, I wanted a handsome boyfriend. Afterward, I chose someone who I wouldn't normally date. With different interests than mine. Dating wasn't for me, just sex. I was never the fall-in-love type, but I didn't want to take any chances. So I selected a few guys and showed them to Frida. Like teenagers, we made a list of pros and cons, and I considered money-quality criteria. It felt kind of odd thinking of them as products, but in the end, I managed to select one guy. He was tall (according to his profile), had green eyes, blondish hair, and a strong jawline. He liked wild western movies, cars, beer, and girls (yes, he put that on his profile). From what I could gather, we didn't have much in common: it was perfect.

A week ago I contacted him and told him my situation. We agreed to have a date before the wedding date, just so we could be on the same page, considering I was going to tell my family that we've been dating for months.

The little café downtown is relatively empty while I wait for him to arrive. It is 4:54 p.m. and he's bound to arrive any minute now. I'm slightly nervous and embarrassed. But I remind myself that none of these people know that I'm a loser renting a boyfriend. Only my 'boyfriend' knows, and he is the loser getting rented.

The door opens and in walks a handsome man. He is just like his profile picture, and I'm not disappointed. He is wearing jeans and a leather jacket over a t-shirt. Simple, I like it. His eyes scan the tables, and he instantly meets mine. He recognizes me from the picture that I sent him. He smiles flirty and with long steps approaches my table.

"Hey baby" His voice is deeper than I imagined. Our only contact has been texting on the app. So it's no surprise if his greetings send shivers down my spine.

"Hello, Dean" If I had met this man at a bar, I would have definitely taken him home. And that's a problem. "I hope this place is to your liking. Please sit." Without waiting for a response, I continue, "I would appreciate it if we do this as professionally as possible, you don't have to woo me like your other customers."

Dean raises an eyebrow in skepticism but sits in front of me and says, "Yeah, I gathered as much from our texts. You are not interested in my company, you just want to fool your family?" It is not a question but sounds like one.

"Yeah, I'm over 30 and single, my family doesn't seem to think that's... healthy, to say the least." Dean nods in understanding and I sense there's a story there, but he doesn't say anything. "So, as I said over the phone, I need a date to my cousin's wedding that pretends to have dated me for four months. I schedule this date before the event, so we can get to know each other a little bit and... pretend better."

Dean tries to conceal a smirk, "You watch too many chick-flicks, don't ya, sweetheart? Sorry to break it to you, but this is my job. I'm not gonna fall in love with you after, like in the movies."

As soon as he says that, the thought of him in bed leaves my mind instantly. I pick him, alright, there's no way I'm enjoying my time with this guy. Does he treat all of his clients like this, or is it because I told him not to fake-like me as he does to his customers?

"Not to worry, sweetheart. I'm not falling for you anytime soon, either," I snark back.

As I'm about to say something else, the pretty waitress that took my order earlier comes to the table.

"Hello, there" her eyes are firmly on Dean. "What can I get for you?"

He smiles charmingly and goes through the menu quickly. "Just coffee and a slice of pie, thanks."

The waitress nods and lingers for a moment longer than necessary, looking at Dean. He pretends not to notice, but when she leaves, he glances at her ass. She moves her hips slowly, it's obvious she wants him to watch.

"Subtle. Not. Is this something you do on all of your dates?" I ask once she's out of earshot.

He chuckles while he takes his coat off. "You just told me the show was for your folks and family only, so I'm turning it off for now."

I raise an eyebrow and play with the spoon in my teacup. "Turning it off? Turning off pretending to be in love with your customer?" I ask.

He shrugs. "That and all the sorts that come with the job," he doesn't elaborate any further.

"Right, well, about the job, I have a few questions." He tells me to go ahead, but the waitress is back with his food, and I wait until she leaves again. "So, my friend, she um- she recommended the app to me, she told me that you guys are certified?"

"Yeah," he responds while stuffing his mouth with pie. He takes another bite and continues talking. Well, the guy was right when he said he was turning it off. "We get a bunch of interviews and tests to make sure we are not psychos. If we pass, then we are hired, and they create our profiles." He pauses as if remembering something, "same thing doesn't happen with the customers, let me tell you."

I suspect there's a story there, but I don't ask. Instead, I move onto my next question. "So, when I signed up, there was this notice listing a few rules for the dates..." Dean watches me warily. The rules were mostly about physical boundaries, such as no kissing or sex. There were also emotional rules for the customer to have in mind that the date was, in the end, not real. "Relax, I'm not gonna ask you to break a rule, I'm just wondering, has anyone ever tried before?"

Dean eases up. "Well yeah, have you seen me?" He jokes. "Protocol dictates for us to reject them or leave the date, then the customer is banned. Why'd you ask?"

"Just curious." He looks questioningly at me. I sip my tea. "Whatever, just tell me about yourself. Only what you are allowed to... do you have another job?"

He brightens up. "Of course, do you think going out with girls pays enough?" He chuckles then adds, "I'm a mechanic. I love cars, I have a beautiful 1967 Chevrolet Impala..." Then he proceeds to tell me all about his car (he calls her Baby) and other curiosities about himself. I notice that he avoids mentioning his family and friends. He also doesn't acknowledge any place where someone might relate him to, like addresses. The boundaries are expected since I'm a complete stranger; a client, so I don't ask him about it.

For the next hours, we get to know each other enough to pass off as a couple. We talk about random superficial matters. I don't have the same limits as he does. He's supposed to meet my family, so I tell him about them. However, I do keep to myself certain personal, private aspects. By the time we are done, the sun has almost set, and he has had another slice of pie and me another cup of tea. Each of us pays for our respective meals, and we part ways with the plans to see each other in two weeks for the wedding. The night is cold when I walk home.