Hey Amanda! Jessica here.

First I just wanted to say thank you so much as always for your kind words about HedgehogsWithoutBorders. We're so happy you've been enjoying it and that it's been useful during your RTW preparations. Yay! And second, as Tim mentioned in his other email, we wanted to thank you for asking such an awesome question. We've actually never been asked this question before (and are hard pressed to think of too many times we've even chatted about it with other travelers). I think it'll be a great discussion point for other folks thinking about their own travels.

I guess probably the biggest caveat that I should mention before talking about how Tim and I interacted with homeless people during our travels is that we both lived in cities for around ten years prior to our RTW trip. I worked in some of Philadelphia's most impoverished neighborhoods, and Tim lived and worked in both Pittsburgh and Philadelphia. (And after our RTW, we spent 15 months living in Washington, DC.) So both of us – whether it was just walking home to our apartment after work or heading out for a night on the town – had a city person's typical exposure to homeless folks prior to traveling. And I'll admit, though perhaps a bit sheepishly, that living in Philly for so long tended to make us a bit immune to what we saw...or, in most cases, what we simply chose not to see.

I write "simply" but, of course, it was never a simple matter. I can't count the number of times my heart would break. I can't count the number of times I'd feel tears come to my eyes as I walked past someone. That said, I can't count the number of times I'd tell myself, "Keep moving, there's nothing you can do for them" or the number of times I felt like an asshole for thinking like that.

I have to balance the choice to ignore or help with the fact that while I don't think a bag of chips can make someone's life better, I do wonder if a bag of chips might not make someone's day better. And who's to say that having one better day wouldn't be the positive tipping point to a better life? I'm a big believer in little moments, or acts of random kindness, making the world a better place.

So what's the solution? How do we travel and interact with the homeless folks we pass along the way? Is there a way we can make a positive difference short-term and/or long-term? And – yup I'm going to ask it (because I think this will be in the back of many traveler's minds even if they don't want to admit it) – is there a way we can travel and not feel like asses when confronted with homelessness?

What follows below are the sort of guidelines Tim and I follow while traveling. Most of them have come about as we've gone along, and some (like the first one) were simply based on our instincts. These approaches definitely help us navigate such a tricky and emotional area, so maybe they'll be helpful to you as well. (Writing them all out makes them look so lengthy, but really everything below was like second nature for us, as I'm sure your choices will become for you too.) Of course, there's a bit of "swiss cheese" morality to it all – some points below just might not make sense to someone else or may even be contradictory, but they felt right to us.

• We never gave money to any person who was outwardly aggressive or dangerous feeling. We didn't want to acknowledge aggressive behavior and certainly if someone felt potentially dangerous we'd never reach for our wallets anyway.
• We never gave money to folks who specifically walked over to us asking for money. Even when they were completely harmless (like the older blind men who would sometimes be walked along the beach by their children in Thailand), being overtly asked by someone walking right up to us felt like an invasion of personal space. And depending on the situation and the person, there could be the potential for something more aggressive to happen.
• We never gave money to children who asked for money. If a child was selling something like postcards, then we might buy some. But we never gave cash or even food to kids outright.
• We never gave money to mothers who were specifically exploiting their children in the hopes of pulling on heartstrings (and wallets). Specifically what comes to mind here are the mothers along Avenue de Florida in Buenos Aires. We'd be bombarded with (adorable) children (sometimes holding smaller babies) who seemed to be wandering the streets by themselves asking for money. After saying no, we'd watch them scurry off behind a bench, get some instructions from their mom, and race over to the next unsuspecting tourist.
• We never gave money to scammers. (No, they're probably not homeless but I figured I'd mention them here anyway.) I'm thinking about the guy who falls in-step beside you as you're walking along the city streets, makes small talk and has a bit of a cultural exchange with you, and then mentions he's trying to get money together to buy a shoe shining box or the like.

So I'd say more often than not, we did not give money to homeless people. But there were some exceptions...

• So we didn't give money to moms begging with their children. But (and here's some of that swiss cheese morality I mentioned above) homeless folks with animals always got a bit of cash from us.
• We'd often give a bit of cash to any homeless person providing a service of some sort or giving a (usually musical) performance. (To be clear: I'm definitely not saying all buskers are homeless! Far from it. But there seemed to be some homeless folks who were buskers, and we thought, "Cool, let's throw some coins into their hat.")
• Likewise, if there was a mom and her children who were sort of doing impromptu selling of snacks or something (clearly not an actual stall or anything, just sort of selling whatever fit in their pockets), we'd usually buy a candy bar or something from her.
• In countries where there were super tiny denominations – like in Cambodia with the 100 Riel note (which is worth about .02 cents), we'd give 100 Riel notes to the homeless people we saw (excluding our caveats from above, like aggressive folks). This would often be the amount that many of the locals gave to the homeless too, so it felt like a way to fit in with local tradition without being all "I'm a Westerner and let me be ostentatious about giving you money."

• Any money we found on the ground was given to the next homeless person we saw (again, with the exception of the aggressive etc caveats listed above).
• If we spotted someone up ahead on our walk that particularly pulled at our heart strings, we'd chat quietly to one another to decide what amount, if any, we wanted to give.
• In an effort to help more folks in the long-term, we sometimes donated to local organizations that focused on street children, landmine victims, homeless families, or homeless women. (We also have a penchant for street dog organizations, but that's neither here nor there!) Some of these organizations had local shops where we could buy handmade items or postcards, for example. Other organizations ran restaurants, like Friends in Phnom Penh, where all the cooks and waitstaff were reforming street kids being provided training. Making donations like this – either direct donations or through purchases – definitely helped ease our discomfort when we thought of the people we had said no to. And, more importantly, it helped make a difference in the work of the organizations we were supporting.
• This next one is a very important point to me: With the caveat of dangerous-feeling folks aside, we almost always acknowledged the homeless people we passed with a friendly "hello" or "how are you?" or "we wish you well" in the local language. Like a bag of chips, a smile might not make their life better (and it certainly doesn't answer any of their immediate needs) but I'm hopeful it made that small part of their day better. People, above all else, want to be acknowledged, you know? And in a selfish way, it also helps me feel better knowing I'm not ignoring "the problem."

• If you do decide to give money, be sure to keep smaller denominations or coins easy to reach in your pocket or in an easy to get to part of your bag. Don't pull out a wad of cash and flip off some bills to hand to someone. The person you're giving the money to might not be a potential threat, but the person standing nearby observing you might be. So just be careful. It's also, I believe, just more comfortable to be able to lean down quickly with small change or small bills rather than stopping and making your donation obvious, which can be potentially uncomfortable for everyone.
• For better or worse, homelessness was harder for us to ignore in Southeast Asia than it was in Europe or South America. This might have to do with the increased amount of physical deformities, like landmine injuries in Cambodia. Or perhaps it was that relatively, the poverty we observed in Southeast Asia was considerably worse than the poverty we saw in Europe or South America. Either way, saying no became a bit more difficult for us – which is why we started giving 100 Riel notes, for example.

Also keep in mind, of course, that the things above are just what we did. (Remember, your mileage may vary.) Your approach might look completely different and that's fine. And if you decide not to give anything ever, that's okay too. There is nothing in the world that says you have to do so. The only thing you have to do is what feels right to you, ya know?

Okay, I think that's about it for our approach to everything – I hope some of this will be helpful! And definitely let me know if any of the above brings up more questions. It's a super important topic and I'm so happy you've given us the opportunity to write about it.

Happy Travels!

—Jessica (and Tim)