More often than not, the men I interact with have an obscene amount of money, hiring me because they don’t have time for relationships, too focused on work and their businesses to care about finding a forever sweetheart. Knowing there was no pressure to give anyone a happily ever after took most of the stress off my shoulders.

I’ve worked hundreds of outings, but I’ve never done an overnight trip. I’m not opposed to the idea; I’ve just never broached the possibility of giving up so much of my precious free time to devote my attention elsewhere.

Four days is a long time. An extended assignment calls for a thorough background check, lots of patience, and a ton of prep. It’s easy to fake a partnership for a couple of hours in a ballroom while eating a meal. Multiple days, however, means being on for a prolonged period of time, no escape in sight.

I’m going to have to really get to know this guy.

The foundation of my business is anonymity. I never expect clients to share their real names or photos of themselves off the bat. A handful of the men are high-profile individuals, hesitant to reveal who they are until the last possible minute.

I get it. I don’t want my services to seem like a traditional dating app. As long as background checks come back clean, and I don’t get any uncomfortable vibes from the man on the other side of the computer and phone, I couldn’t care less about what they might look like. I’m not doing this to date the hottest man in the city; limiting myself to events with only the most subjectively handsome men hinders how much money I can make.

And I really want to make money. I’m tired of living paycheck to paycheck, and ready for financial freedom once and for all.

All the inquiries I receive, including JD’s, follow a strict procedure: We start by sharing basic information and submitting a background check. After the data comes back clean, we begin the process of getting to know each other, diving deeper into why they want to hire me.

Communication with a client starts strictly via email. It’s more open-ended and formal, giving the man time to back out without divulging too much information if they don’t feel like continuing the arrangement.

After a week of computer interactions, we transition to texting, done through a third-party app. Safety is paramount to me; I don’t need random people knowing my phone number in the off-chance things go south and take a steep nosedive toward freaking weird.

There’s nothing monumentally profound discussed in the text messages, but it’s significantly less rigid, more friendly, and super laid-back.