My girlfriend keeps trying to postpone our trip

There’s three ways this can go, right?

1. You can stay home and put it out of your mind.
2. You can go on the trip without her.
3. You can find a way to take the trip together.

I get the sense that the first option is a non-starter. So what are you left with? If this relationship is really important to her, and after five years I sure hope it is, then you can probably blackmail her into going by threatening to pack up and go without her. But would that really be your dream trip? Nothing sounds less fun to me than dragging around someone who wishes they were home and shows it.

Instead, I’d suggest making a serious and thoughtful effort to figure out what’s really keeping her home. Even if it was just a romantic fantasy for her, there’s nothing better than turning a fantasy into reality — and you can be the man who made it happen. Chances are, she’s hung up on one of the same three bugaboos that are holding a lot of other travelers back too: Could it be fear of the unknown? Money worries? Concerns about a big gap on the résumé?

These are all legitimate issues, but they’re not worth missing a dream over.

Fear of the unknown is in many ways the hardest one to conquer, because it’s not completely rational. You can’t debate someone’s fears away. The most important thing is to be understanding, because otherwise it can grow into a barrier that prevents her from wanting to discuss the trip at all. And to the degree that you share that fear, be open about it so that it becomes something you’re working on together.

By comparison, money worries are a whole lot easier to work with. Draw up a budget for the trip. Negotiate about which luxuries and destinations you can do without — by cutting short that swing through Europe and using the time in Latin America instead, and staying in youth hostels while you’re in the more expensive countries, you might make that budget significantly smaller.

Many people seem to think that if they just wait a few years and sock some money away, they’ll be better able to afford an ambitious trip. But I’m not so sure about that. When you’re young, you can sleep in a $2 thatch-roofed beach hut and it’s a fun adventure. Spend a few years working, building up your bank balance and getting comfortable, and next thing you know you’ve turned into a person whose ideal vacation features a whole lot more air conditioning and hot showers. The corrolary of this, of course, is that someone who doesn’t feel rich enough to travel at 22 with $5,000 in the bank, is probably going to feel the same way at 27 with $15,000 saved away. So make the trip fit the money you have. Missing out on a few destinations is better than missing out on the whole thing.

That leaves us with the easiest hurdle of all, the résumé gap. Remember when you were 12 years old and acted up in school, and the teacher warned you that your misbehavior was going to end up on your Permanent Record? It sounded pretty scary at the time, but I’m going to let you in on a big secret: Nobody cares about your epic lunch-hour spitwad battle with Jimmy Sanders. You are forgiven.

It works the same way with your résumé. The only time a gap is an issue is immediately afterwards, when you’re looking for your first job after the trip. Once you’ve got some productive experience under your belt, that’s what matters. And that’s not all — many returned long-haul travelers report that their journey actually helped them in interviews: It provides a wealth of examples that can be finessed to demonstrate your cultural adaptivity, financial acumen, and overall resourcefulness. And the more places you’ve visited, the greater the chance that one of them is your interviewer’s dream destination too.

Of course, your girlfriend’s issues may be slightly — or very — different from these. But the basic point is the same: If the idea of travel appealed to her, then the reality can too. You just have to figure out how to get her there. Ultimatums won’t do it, and they aren’t necessary. Listening, planning, and compromise are your best tools.