Dear Prudence,
I’ve admired a woman from afar for the past year. She recently broke up with her boyfriend. They still live together, but she’s trying to move out. Since the breakup, we’ve often seen each other at get-togethers. At one of these events I mentioned that I was planning a trip to Tahiti this summer. Weeks later, she texted to ask whether I was still going. We have since talked about going together, which I would love. I’ve asked her out a few times, but she only joins when other friends are involved. Recently, she said that while we can be great friends, she doesn’t think we should date. She also said that once we get to Tahiti, we shouldn’t hesitate to split up and go our separate ways. I dread the thought of getting stranded alone for two weeks of holidays. She’s an academic, so the Tahiti trip corresponds with her annual sojourn. Should I call off the trip with her now, so that she doesn’t rely upon me for her holiday? Or should I continue planning for the trip and hope for the best?
—Romantic Getaway or Free Ride?