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And about a month later, I was boarding a flight to San Francisco and preparing to spend two days on the Golden Coast with a stranger. Full disclosure: the PR firm covered both of our expenses (including separate hotel rooms), and I'd had a chance to chat with Josh in advance, so I knew from the get-go there was zero pressure to "earn my keep," so to speak. Admittedly, our travel styles were fairly different (I'm more of a "let's wander down side streets and nap in the park!
I checked into the hotel around 2 p.m., a few hours before Josh was set to land, on cloud f*cking nine. Even if Josh was planning to murder me, it all seemed worthwhile. After all, I couldn't escape this with a fake panicked phone call from a friend or a "work-related emergency" (my exit plans for bad Tinder dates in the past); I was stuck with this human for a full 48 hours.
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We spent the first night strolling through Pier 39 and eating tacos in the Mission and day two snapping pictures across the city, from Alamo Square to Crissy Field. " Josh ordered a car as I burped on the street corner, thinking, "If he'd had any hopes tonight might take a romantic turn, I am definitely killing them right now." We rode back and parted ways in the elevator, and I wished Josh a good night before throwing up for a few hours in my room (how charming! Fortunately, I felt totally fine the next morning, and Josh didn't seem to resent the fact that my weak stomach had ruined his night out on the town.
We decided to take a nap break that afternoon (thank goodness), and when Josh suggested we head to Land's End to watch the sunset later, I wasn't even afraid he'd push me off a cliff. We grabbed brunch at Mama's on Washington Square (FYI: the cranberry orange french toast is well worth the wait), packed up our things, and headed to the airport.
When I was first pitched on the idea of Miss Travel — a dating site designed for singles to find travel partners (think with Caribbean getaways instead of dinner and drinks) — I thought, "This sounds like a ploy to get me into sex trafficking," not, "This is going to end with me dry heaving in front of a San Francisco strip club." But life is full of surprises, and evidently, so were the tacos I'd purchased that night. After reading a piece I'd written about why women should "get on the plane," a PR representative for Miss Travel slid into my inbox and asked if I'd be willing to apply this adventurous philosophy to my dating life (i.e. A few cursory Google searches suggested that it was created for attractive women looking for sugar daddy vacation sponsors, and I was terrified. But I'm not one to turn down a free trip or the chance at a crazy story. I wandered around Chinatown and North Beach for a spell, feeling like I could definitely get used to this travel blogger lifestyle, then met him for drinks at the hotel restaurant around 6 that evening. But I guess that's kind of the challenge of traveling with anyone, right? Conversation with Josh was easy, and the lulls were never awkward.
As someone whose default fears in virtually every situation are that I'll be murdered or sold into the sex trade, traveling with a sugar daddy seemed like a horrible idea . So with a push from my mom (of all people) and sister, I agreed to give it a go, sex trades be damned. Not only was my travel date — we'll call him Josh — far from the 50-year-old in Boca I'd feared, but he was also a natural-born Instagram husband and down to keep things strictly platonic. Though I'd already spoken with Josh here and there, the socially anxious side of me was heavy breathing over my daiquiri. He was cheerful, exceptionally friendly, and happy to pass chunks of time silently scrolling through his phone.
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