Should I go on a crazy journey with a girl I have feelings for?

beach-vacation-people-sandTravellerofWorlds asks:
I met her last year at college and we’ve been rather good friends ever since. I never really managed to ask her out due to several reasons, one of them being my insecurity with certain aspects of life. Anyways, we both travel a lot and always keep in touch when we are on the other side of the world. Now she sent me a link to a video where some US students try to live in South America for 1 dollar a day, to experience poverty and broaden their horizon. I was totally hooked and asked jokingly if we’d do the same thing. And she said yes. I told her that I’m serious and she said she also is. So we already made our first plans on where to go and I started learning the local language. The thing is, I have a crush on her and I’m not sure she does.

So what would be the best thing to do before leaving? Should I confess my feelings before leaving and risk not going to this amazing journey or do nothing? Help!


Demetrius says:

You know honestly, I’m sort of struggling with how to answer your question. On the one hand, I always encourage people to be honest and open about their interest in others. On the other hand, those people tend to not have huge international trips planned together. I’m hesitant to say “Just tell her how you feel” because most people can do that and have the luxury of being rejected and never seeing the person again. You don’t have that luxury and it’s very possible that she could flat-out reject you, and then you’re both in a foreign country together where you have to rely on each other. Like I said, this is not a simple question or situation, which I love by the way.

I’m not sure what your level of commitment is here in terms of planning. Did you already buy tickets and accommodations, or is this a theoretical trip at this point? That does change my answer a tiny bit. Another factor is a question you need to answer: What’s more important to you in this scenario, the trip itself, or taking the trip with her?

If you’re more focused on the trip instead of her, and if nothing has been purchased for the trip, by all means tell her how you feel. Best case scenario the feeling is mutual, you get to go on an awesome vacation with a friend you’re attracted to, and maybe you grow closer on the trip. If you’ve paid for any travel or accommodations for the trip already, and you care more about the trip than being there with her, you might want to tell her, just know that you risk either making the trip really awkward, or her deciding not to go on a trip. I can’t think of a situation as bad as planning a trip with someone who is attracted to you that you have no interest in. Again, that’s the worst case scenario, and I’m playing devil’s advocate here. It’s entirely possible that she’s into you and telling her your feelings will only heighten the enjoyment of the trip. Or not. Just know what the risks are before you decide on a plan of action.

If taking the trip with her is more important than anything else, tell her you’re attracted to her after the trip is over. You can flirt with her before and during the trip, but don’t put her in a position where she’ll be uncomfortable because of your flirting or advances. It sounds like an amazing experience to undertake, and it also sounds like an amazing experience to do with a friend so if I had to choose a plan of action if I was in your shoes, this is what I’d do. If you want the trip to be about bonding together, I’d avoid telling her about your feelings until you’re both a position where you don’t have to rely on each other. I’m sure that if she spends enough time with you, she’ll realize you’re attracted to her. Alternatively, if she isn’t into you right now, spending that much time with someone can help build a bond and could potentially lead to her growing romantically interested in you. It would definitely be a good idea to hold off and let things develop if you want to do this trip with her.

Personally I wouldn’t plan a trip with someone I was kind of sort of interested in dating, but screw it, what do I know? Whatever you decide to do, just be aware of the risks, and what your actions might mean and the reactions they might elicit. If you want to date her more than you want the trip, ask her out now, especially if you haven’t paid for anything. If you want to do the trip with her more than you’d want to date her, don’t tell her how you feel until you get back home. Best of luck with whatever you decide!

Good Luck Out There.

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