Taking a trip with someone that you’re not seriously dating is RISKY. Will you be compatible? Will it be a miserable weekend? Or you might get a little insecure and become judgmental of yourself; What will my friends think? Would my parents approve of this behavior (note: who cares what they think)? Is this “weird” that I’m taking a trip with someone I barely know?
These are all valid questions and concerns. But I’m here to call BS, and encourage you to challenge these fears! Life is too short; it’s important to take risks, go outside your comfort zone (free of judgment from others), and introduce more spontaneity in your life. In Chapter 11, “An Epic Second Date” of my book Wise Millennial, I chronicle my adventure of taking a girl I had just met on a second date to Buenos Aires for a long weekend. Yes, you read correctly, a second date. Was it risky? You bet. Had it worked out and we ended up together, I would say “it was the greatest decision I’ve ever made.” We still had an amazing time and learned so much about each other (and ourselves!) in the process, despite the fact there wasn’t a third date. The important thing is to appreciate it for what it is: an exciting adventure.
Here are some real tips on this unique and semi-controversial topic, based on my spontaneous travel experiences I’ve had with a few different girls:
– 1) Take short trips, with cheap flights. The flight should ideally be under three hours (no connections, or one max), and less than 4 days total. Don’t spend more than a few hundred dollars on each ticket. This should be fun, and obviously a little extravagant. But don’t put yourself under so much financial strain that you’re going to be thinking about how much it cost the whole weekend.
– 2) SEPARATE ROOMS – Yes, taking a trip can potentially be a very romantic act. But this is NOT a solicitation or guarantee of sex and/or anyphysically romantic activity, for that matter. In fact, you should go into the weekend with the mental expectation that there won’t be any intimacy. Do you still want to go with this person? What’s the real intention here? Remember, this is just another date (whether it be your 3rd, 4th, 5th, etc).
– 3) Offer to pay. But don’t set yourself up to be used. Inviting someone to take a trip is an incredibly generous and thoughtful idea. Just be careful not to set a false expectation or dangerous precedent that “this is how life is always going to be like,” either. Stay within your budget. Don’t book five-star hotels (unless you agree to split it). If he/she doesn’t like you based on which hotel you choose, that person probably isn’t “the one.”
– 4) Check local culture/food restrictions! Pretty comically, it wasn’t until after we had landed in Buenos Aires (a very meat-heavy culture) that I discovered my date was vegan! While we were able to laugh about it, I was stressed the whole time worrying. It didn’t even occur to me to ask because in most major cities in the US there are lots of options for any special diets!
Dating through travel experiences can be a great way to get to know someone, if an unusual method. Don’t put yourself under too much pressure if you try it out–It’s just another date (granted, in a unique location)!
Peter N. Darrow is a Millennial, a native New Yorker, an entrepreneur, and an expert at learning from his mistakes. After earning an MBA in entrepreneurship from Babson College in 2014, Peter founded Darrow’s Farm Fresh restaurant in Union Square in NYC. A health and wellness entrepreneur with a passion for helping people, Peter has already seen much in the way of success and failure, and speaks to the challenges facing his generation, and dispels myths about what it’s like to supposedly “have it all.” He is the author of “Wise Millennial: A Field Guide to Thriving in Modern Life” publishing April 30, 2019. Find out more about Peter at www.wisemillennial.com.