When Jake* got desperate for cash a couple of years ago, he hit up SeekingArrangement.com, a dating site for aspiring sugar daddies and cash-starved younger people. Not long after, he found himself in a relationship with a daddy who seemed to want, above all else, a son, to do things like check out baseball games and shop for produce. The platonic relationship continues to this day.
What was the impetus for all of this?
I dropped out of college halfway through my freshman year because I landed a great job. When that job didn’t pan out, I decided not to go back to school, which has since made things very difficult financially. I had a friend who’d been making money from someone she met at Seeking Arrangement for a long time. He covered her rent and more. He offered a lot, but she had to offer a lot in return. She persuaded me into giving it a shot and assured me that it didn’t need to be sexual and that it could stay purely platonic since there were plenty of people out there who were just looking for a friend.
Had you done sex work before?
I gave phone sex a try for about three months. The money was okay, but it was tough to build a client roster and the hours were inconvenient because I had to be available to talk on the phone at the sexiest times — i.e., very, very late at night. It was, however, a big push for joining Seeking Arrangement because I realized that a lot of people just need someone to talk to. In fact, many of the calls ended up pretty tame; they just wanted to talk about their day.
Is it hard to join Seeking Arrangement?
Not really. It’s essentially like OkCupid. At least it was back then. I can’t speak for it now.
Did you give a lot of thought to how your crafted your profile?
I was kinda flippant about the whole thing, to be honest. I was, though, explicit that I wasn’t there to offer any sexual interaction. I was as straightforward and as blunt as possible about that in my profile.
How did you decide who you would meet up with IRL?
I was waiting for some subtlety. I would ignore anyone who said something explicit right off the bat, which, like most dating platforms, was 90 percent of the time. It was still hard to tell, though. The first guy I met up with for dinner (post-sunset, very posh, all red flags) totally swindled me; a few minutes in, he already started throwing out numbers: “If you’re willing to be my partner, I can offer you X amount of dollars.” Oral would have been $300 each time. I had no fucking idea if that was a good price or not. Maybe I missed out on a great opportunity, but I was like, “No, thank you. … But thanks for dinner!”
How quickly after meeting with that guy did you try again?
It was another couple of weeks before I met the man I’m involved with currently. He had a very tame approach, which is why I engaged. He said he was looking for something platonic as well and that if I wanted to meet, he was interested. Our meeting was on neutral ground — at a restaurant, in the middle of the afternoon — and I immediately felt more relaxed than my first excursion. He was delicate not to talk about the money or mention the site. It was abundantly clear that he had a lot of distaste for the steps it took to get here. I think this had a lot to do with the fact that we authentically hit it off. He was in his late 60s, handsome and casually well-dressed. He told me he was divorced (from a woman) and had no children. We stuck to small talk; I think we both decided quickly that this was what we were looking for.
What was the financial arrangement?
He was curt about it. At the end of the lunch, he told me he would pay me $200 a day just to hang out. I asked him what that would entail, and he bullet-pointed some hobbies. He said he would cover the cost of whatever we ended up doing. Like if we went to a baseball game, he would buy the tickets. Basically, $200 on top of whatever he was treating me to.
Did he give you any sense of how much he wanted to hang out?
Nope. He was very vague. Which I found very alluring. I really got a kick out of it. I knew this was going to be an experience even if it was only for this one day. Admittedly, I was surprised by how curious I became. I had no idea where things were going to lead.
When did he call you next?
About two weeks later. It was so long afterward that I assumed I hadn’t been his taste. I ignored his call — it was from a number I didn’t recognize — and received a very formal message that was vague enough that if it were ever heard out of context, you’d have no idea what the relationship was. Ever since, he’s been just as careful to communicate in this manner. I called him back, and the first thing we did was go to the farmer’s market.
It was a lackadaisical way to meander, talk, ask questions and suss each other out. He wanted to know what I did — both for work and fun. I didn’t pry into his life because I assumed he wouldn’t want to talk about it. He would occasionally pepper in anecdotes about an experience he’d had or where he’d been on vacation. At that juncture, I couldn’t gather what he did or where lived. I also began to wonder stuff like, Would I ever see his place? We ended up spending an hour and a half at the market. He bought himself a few groceries and a bouquet; I insisted I needed nothing.
I figured that we would go someplace else, because how could this possibly be worth $200 to him? But we didn’t. He didn’t say anything about the money either. Instead, he shook my hand goodbye and pulled the slick move of handing me cash within that motion.
And he never once made any kind of move?
Not once. Nor the next time. Or the time after that. So much so that I began to second-guess myself: Am I doing this right? Should I be doing this at all? The whole experience started to make me anxious because these hangouts couldn’t just be it. They were too simple. I began to wonder if he was sterile.
Why?
Something was amiss. It was like he was filling a void — caused by what, I don’t know. It became so paternal so quickly. Slaps on the back. Sincere, eager interest in my well-being at work and socially. They way he dished advice was so sage-like. And he was protective. Over the years, he’s even helped me career-wise. It felt like he was playing dad every time I was with him. But much like an actual parental figure, I don’t tell him everything. In fact, I often lie.
Do you think he’s roleplaying because he’s lost a child?
That’s what I wonder. Even after all this time, though, I’m careful not to ask about it. Because again, our relationship has never not been transactional. It’s understood he needs someone to hang out with, and we have still yet to touch on why. Only one thing is certain: It’s a father-and-son dynamic. That’s definitely what he needs.
What if things stopped being transactional?
I’m sure he would simply become a deeper mentor. But I couldn’t tell you whether or not that would be a comfortable transition. It fucks with my conscience to have perpetuated this for so long. It speaks volumes of me.
I do well to make sure he doesn’t ever feel taken advantage of. I’ve kept a lot from him that could potentially be spun as if I were fishing for more. There was a period where I was so down and out that I was living in my car. He will never know that. It would destroy him. No doubt he’d be overjoyed and insistent to lend a hand, but I couldn’t deal with that. I just couldn’t. I hesitate to use to word “inappropriate” in a scenario as socially unorthodox as this, but it would most certainly feel inappropriate.
How often do you see each other now — two years after you first met?
Maybe once a month. The last time we hung out, we went to a museum. It was a quiet excursion, with little exchange. Some of our hangouts are like that. There was even a point last year when I didn’t hear from him for over three months. When I did eventually hear from him again, we didn’t discuss why. It’s important to note that I never call him.
How well do you think you really know him?
I know what he does and who he is. He’s of a specific age and wealth that keeps him from having a social media footprint. Everything he’s told me, though, definitely checks out. Of course, I ran with what little I know. I also know that he dates. That was shared pretty quickly, actually. “I’m seeing this new woman,” etc. I will tell him about the people I’m dating — to an extent.
He never seems jealous?
No, but he remembers and checks in. He’s genuinely concerned about my well-being.
And it’s never strayed beyond the paternal?
I’ve never once gotten a touch, look or tone of voice that suggested more. Nor has he ever invited me to his home. We always meet somewhere neutral. It took several months for us to hug hello or goodbye. Even now, it’s a handshake-pulled-into-a-hug. And sometimes that gets totally botched and is very stilted. He’s a very, very, very well-disciplined man across the board. It’s easy to speculate as to why, but with this many secrets coming from both sides, it’s easiest to just take it at face value.
What would happen if you stopped responding to his texts or calls?
I think he would take that with a lot of grace.
Have you talked about the future of your relationship at all?
No. Though financially, I’m at a point where I don’t rely on it like I used to. The initial need has run its course. At least, on my end.
How would you feel if he stopped texting or calling you?
That his needs had been fulfilled or that they were being fulfilled elsewhere.
You wouldn’t miss him?
I wouldn’t miss the charade, that’s for sure.
*Name has been changed.
Josh Schollmeyer is MEL’s editor in chief. He last wrote about an equally dysfunctional relationship between a father and son—Vince and Shane McMahon.
More from The Daddy Issue:
- When Mom and Dad Call Each Other Mom and Dad – MEL Magazine
- Fifty Shades of Daddy – MEL Magazine
- Weed Has A Daddy, Too – MEL Magazine
Josh Schollmeyer
Josh Schollmeyer is the co-founder and editor-in-chief of MEL. Previously, he dreamt up the popular Kinja site Playboy SFW, an effort to bring back the brand’s commitment to social-sexual values (but with a 21st century sensibility), and helped make The Chicagoan, a coffee-table-book like magazine that doubled as a love letter to his hometown and that sold out in under a month. He’s written a bunch of stuff, too, most notably, the best-selling ebook Enemies, A Love Story, about the bromance between dueling film critics Gene Siskel and Roger Ebert. (The Atlantic included it as one of the 10 Best Oral Histories from 2012 You Haven’t Had Time to Read Yet — admittedly, it was very long.) He later served as a producer on the Steve James-directed Ebert documentary, Life Itself, which was short-listed for an Oscar and won an Emmy. He was most recently named to AdWeek’s Creative 100 in the media innovators category, and chosen as a finalist for Digiday’s 2020 Publishing Executive of the Year. In another life, he helped The Bulletin of Atomic Scientists win a National Magazine Award for General Excellence. He is generally the tallest blond of any room he’s in.
