Then it hit her: They'd be together four straight days. What if they got in a fight? What if a really annoying personality quirk emerged?
What if they broke up before they even left?
"I was like, 'Oh my god, the trip is as far away as we've been dating,' " Gresh said. "Hopefully nothing goes wrong in the next month because we're both going to be out a lot of money!"
Despite a missed flight, cold weather and her admittedly annoying, compulsive search for the cheapest airfares, the duo found they were compatible. By the vacation's end, their relationship had passed a major test: the holidate.
Long gone are the days when a young couple's first trip together was the voyage home to meet the parents. Lured by the ease of Internet travel planning, couples are jetting off to the beach, piling camping gear into the car and putting their relationships to the early test.
The hotel and tourism industries are starting to take note. Fairmont, a luxury chain of 55 hotels worldwide, has begun offering packages designed for new couples, including "icebreaker" specials that pair romantic dinners with more adventurous outings. The Ritz Carlton Orlando Grande Lakes suggests Orlando, Fla., as a "great destination to be the first mark on your love story map," packaging a lake-view room with tickets to Discovery Cove, an upscale water park.
"We think we've got something here that's satisfying a need," said Brian Richardson, Fairmont's vice president of brand marketing and communication. "I'm not going to suggest it fell out of any profound, deep scientific research. . . . There was just evidence to suggest that couples fairly new in a relationship are increasingly interested in traveling together, doing interesting things together and wanting to make an impression."
To test its hunch, Fairmont partnered with Lavalife, a Canada-based online dating site, to survey whether people in new relationships would consider traveling with their partner -- and how soon they'd be comfortable heading out of town. Of more than 5,500 people who answered the poll, 50% of men and 41% of women said they would take a trip within the first two months of dating.
Fairmont's concierges noticed the trend after fielding calls from anxious men trying to plan the perfect romantic weekend. They desperately asked for advice: Red roses or yellow? Is a dozen too many? What should we do for fun?
Concierges were surprised to learn the guys weren't planning engagement proposals or anniversary celebrations.
"They're always very honest and upfront: 'I'm bringing my girlfriend. We don't know each other all that well, but I want to show her a really good time,' " said Judy Mendel, chief concierge at the Fairmont Mission Inn & Spa in Sonoma, Calif. Although the potential for disaster is there, she said, a holidate isn't necessarily a bad idea.
"It's like I told my kids: Travel with your prospective mate before you marry them because if you can't travel with them, you've got a problem," Mendel said. "It's a good test of a relationship."
For Gresh, who lives in Toronto and works at website Travelzoo.com, and boyfriend Glen Bastedo, 30, who has backpacked in 32 countries, travel compatibility is a relationship requirement.
"It was kind of like the true test," Gresh said.
Bastedo said that as they were planning he didn't know whether it would work out, but going on the trip seemed natural.
Of course, all trips don't end well. Elizabeth Buckser, 23, of Pasadena drove from California to Pittsburgh with her college boyfriend, her sister and her father a few years ago.
"It was a disaster, an absolute disaster," she said. The couple, who had been dating six months, broke up not long after the 11-day trip.
She said her boyfriend expected her father to pay for everything, but tried to dictate where they should go and what they should see. Yet he grew uncomfortable being alone, even when she wanted to take a nap, she said.
"It told me a lot about his character and who he really was," said Buckser, who works for a theme-park planning and production company in Burbank. Without the trip, she said, "I might have been with him a lot longer."
Kim Hughes, editor in chief of Lavalife, said the Internet had made last-minute travel easier for singles looking for more unusual dates.
"Dinner and a movie sometimes seems a little passe," Hughes said. "The whole dance of dating is to find out compatibility. It's as much what you can't live with as what you can live with." Traveling together is "a litmus question."
Such pressure is what has men -- and it is mostly men doing the planning -- dialing in to Fairmont's concierges.
Jim Carey, director of concierge at the Fairmont Copley Plaza in Boston, said he typically planned a lot of activities for couples on their first travel date.
"You don't want to spend too much time just sitting together in a room," he said. "You want to keep busy the whole time."
That's exactly what Gresh and Bastedo planned: tobogganing, ice skating, dancing and a visit to an art gallery.
By the end of their long weekend, Gresh said she had seen enough to know the relationship was headed in the right direction. When she was grumpy and cold, Bastedo suggested stopping for a cup of coffee. When they missed a connecting flight, he remained calm. With the first trip out of the way, they're planning more.
"We're going to New York in April," Gresh said, "and then I think we are actually going to commit to a weeklong trip the last week in June, renting a cottage."