[Edit: I've moved! If you're interested in up-to-date info on free travel, check out Free Travel in Your Twenties]
One of the biggest shocks I've encountered in my points obsession thus far came shortly after traveling to the Caribbean with my wife. I had paid for both tickets with my card and listed my frequent flyer account number for both of us, yet only received points for one traveler! After doing a lot of digging into what I could have possibly done wrong, I learned that points only count when the name on the ticket matches the name on the frequent flyer program. In other words, you have to be the one doing the actual travel in order to get the miles, regardless of who pays for it. Turns out this was a rookie misconception on my part, and I consider it one of my two most important lessons learned - the other being that you do not earn points for travel paid for with points.
The silver lining was that most airlines allow you to retroactively redeem points within 60 days, so I set my wife up with an account, looked up her ticket numbers on our email confirmation, and therefore ended up still getting the miles for both our tickets. But now what? It's a rare exception for us to travel together, so it won't take long before our accounts have significantly different amounts of miles. I can't put both sets of miles into the same account, but I also don't want those points to go to waste!
Some frequent travel programs allow you to pay a fee for transferring miles. For example, Delta SkyMiles can be transferred for $0.01 per mile plus $30 per transaction - a terrible deal, since most miles are only worth $0.01-$0.02 miles each! There are a few other programs, like British Airways Avios, that let you combine miles as long as you share the same address. Be sure to check with each program to see if it's worthwhile for you to combine points into one account.
The advantage of combining your miles is that the extra miles help you reach award levels faster, but it is a rare case that you can transfer miles without penalty. An alternative option is to use the two accounts to book separate awards. For example, I could save up my points until I had two reward tickets from the US to London. During the time it took me to save those points, perhaps my wife traveled much less, but still enough to redeem two much cheaper award tickets from London to Paris - I could then book those tickets using her points!
The final option is something called a Companion Pass, which is exactly what it sounds like - an extra ticket for your companion! There are different ways to get companion tickets - the British Airways Visa gives you one companion ticket when you spend $30k in one year (yeah, right!). Other cards, like the Alaska Airlines Visa, offer one companion pass per year for only $99. Companion Passes can save you a ton of money - obviously, the more expense your ticket is, the more money the pass saves you. The $99 Alaska Airlines pass could be used for a first class flight to Hawaii, saving you up to $2,000!
Southwest Airlines has a slightly different promotion - earn 110,000 miles in a given year, and you'll receive a Companion Pass good for the remainder of the year plus the entire year following! This means the name of one person of your choice gets put on the Companion Pass, and they fly with you free as many times as they like for up to two years! Keep in mind though that the 110,000 miles have to be earned from flying (or credit card sign-up bonuses), not from things like credit card spending, free surveys, bonus miles, etc.
Most hotel programs allow you to earn points from up to two rooms per stay, as long as you are paying for them both. If you're traveling on a budget, sharing a room is still a much cheaper way to go overall. But if you're organizing a trip that includes others that aren't into free travel (parents, perhaps??), this can be a great thing to keep in mind!
Overall, things tend to get more complicated when traveling with another person. Coordinating schedules, needing twice the miles, finding double the award space available... But if you can start your planning early and perhaps take advantage of a few of these tips, hopefully some of these downsides can be mitigated. And remember that it's always more fun sharing travel experiences with someone else!!
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