A Real Story

I signed up for Seeking during my second year of grad school with $34,000 in loans and a very specific plan: no sex, just paid company, maybe $2,000 a month. I built a whole spreadsheet before I even matched with anyone, columns for hours spent, gas money, what counted as a ‘date’ versus a ‘meeting.’ The first guy, I’ll call him R., was 58, ran a commercial roofing company outside Sacramento, and took me to a steakhouse where he ordered for both of us without asking. He was polite. He tipped 30 percent. He also texted me at 11:40pm on a Tuesday asking what I was wearing, which was not in my spreadsheet anywhere.

The arrangement with R. lasted about six weeks and $3,200, and it genuinely helped, I paid down a whole loan servicer balance. What wore me down wasn’t the dates themselves, it was the emotional bookkeeping in between, figuring out how enthusiastic to sound in texts to keep the allowance steady without giving him the impression I was actually his girlfriend. I started rehearsing responses in the Notes app before sending them. That’s when I noticed I was working a second, unpaid job just managing his feelings about the first one.

What finally ended it was small and almost funny: he asked me to come to his daughter’s college graduation as his ‘plus one,’ no romantic pretense, just company, and offered an extra $500 for the day. I said no and he got genuinely hurt, not angry, hurt, like I’d broken some understanding neither of us had put in writing. That’s the part nobody tells you going in, that the money is the easy, clean part of these apps, and the ambiguity around what you actually owe someone emotionally is the part that costs you.

I still think the model can work for some people, I know a woman from a forum who’s had the same arrangement for three years and calls it the best part-time job she’s ever had. For me, the spreadsheet eventually had a column I hadn’t planned for, labeled ‘how tired am I after,’ and once that number stopped being worth the deposit, I deleted the app.