Charlie’s Rules for Traveling with a Woman

Huge BoobsI love to travel.  The new experiences and perspective I gain from a trip can be one of the the most rewarding things in life.  And while traveling with your team to foreign lands filled with spicy food and chicas calientes is certainly one of the great pleasures in life, sometimes I like to mix it up and bring a girl with me.  No one enjoys holding court with my bros at the perfect location at the bar or club surrounded by our new Russian girlfriends drinking Russian Standard Vodka more than me, of course.  But it’s also nice to travel for other reasons and sometimes a romantic trip with the right woman to a tropical paradise is just perfect.  However, there are some major pitfalls to avoid, unlike a trip with your bros a trip with the wrong woman can go south in a real hurry.  Not south to Mexico south, more like south like William Wallace’s attempt to conquer England south (I love that movie).  If you’re in a bad relationship nothing will expose the flaws of that relationship more conclusively and obviously than an international trip.

So I present to you: Charlie’s Rules for Traveling with a Woman.

Rule 1:  Bring the right woman, or rather, don’t bring the wrong woman. This is obvious advice but often ignored.  I’ve done it, thinking, “Oh I know I’ve seen the warning signs, but I’ll choose to conveniently ignore them.  I’m sure that once we leave the country all of her personality flaws will just melt away and influenced by the beautiful weather and palm trees that everything with us will be perfect.”


Traveling brings out the worst in people.  The Romans said in vino veritas (in wine, truth), and I say as a corollary, “In via veritas”, which translates roughly as “If you bring a pain in the ass bitch to Malaysia, she will become 10 times the pain in the ass when you get there.”  (Note to you-know-who, of course I don’t mean you, let’s go to Langkawi again tomorrow.) As you see I am quite the Latin scholar.  Let’s do a brief rundown of personality issues to consider.

1.  Don’t bring a High Maintenance Woman (HMW). – Traveling is by definition often messy and unpredictable.  You may show up somewhere and find that your accommodations are less than ideal.  Or you may find that you have to ride a Guatemalan chicken bus for a little while.  Fine, no big deal, you gotta roll with it, right, that’s part of the fun of traveling anyway, right?  But a high maintenance woman needs to have everything just so.  If she has a problem with something, it becomes your problem.

2.  Don’t bring a stupid or helpless woman. – When traveling, whoever is with you is a team member.  If you’re traveling with a dumb or generally useless girl she is going to need extra looking out for and will not add anything to the team’s strength.  Carrying around dead weight on a trip is exhausting and aggravating.  If something bad happens like getting in trouble with cops or criminals, losing passports, missing flights, etc, you will need a competent person to help you navigate the situation.  Plus when you travel with a woman you will be forced to spend time with her pretty much nonstop so if she says a bunch of stupid stuff all the time it will get very aggravating.  Remember you can only have sex for a small percentage of the time of a trip, but you will have to talk to her the whole time.

I was on a trip to France once with a completely retarded but hot American model girl and she just said a knee-slappingly idiotic thing every ten minutes.  Once we were at a restaurant and the menu in French said, “Nos entrees, Nos plats, Nos desserts, etc.”  She looked at it and asked:

“So does this mean, ‘Not desserts’?”.

Now mind you there were things listed in that category like crème brûlée and chocolate mousse.  I said:

“No sweetheart, it’s French so “nos desserts” means “our desserts”.

“Oh, I see.  Can we have dessert?”

“Of course.”

Then the next day at dinner she asked the same question.

3.  Bring an outgoing woman. – When traveling as a couple it is much more difficult to meet other people and get into trouble (the good kind).  People are less likely to approach a couple so the onus of extroversion is on you.  Having a nice friendly outgoing chick with you makes a huge difference in who you meet and how much fun you have.

4.  Take a woman with similar interests. – When I travel I like to sleep in, then sit around at cafes doing nothing during the day with the occasional stoned trip to the museum, and then I like to go party my ass off at night.  If some chick I’m with want to drag me off on touristy trips to boring ass old churches at 9 in the morning, one of us is not going to have a good time.  Make sure you discuss beforehand what you want to do with your time on vacation and make sure you’re both on the same page.

5.  Don’t take a woman you haven’t slept with yet. – The temptation is strong.  I think often, “This chick is super hot and we seem to get along, so a trip to Playa del Carmen will totally seal the deal.  Mistake.  Sometimes this works out, but the truth is that you never can really know how well you will get along with a girl until you sleep with her.  Plus the absolute worst thing ever is when you go on a trip with different expectations about the nature of the relationship.  Chicks will accept trips and somehow convince themselves that you’re “just friends”.

One of the lamest travel experiences of my life involved a girl I had briefly hooked up with but not slept with while she was “on a break” with some long term douchebag boyfriend who subsequently forbade us to contact each other.  When they broke up, she promptly called me up to tell me and I said, “Great, let’s go to Vegas.”  So she agreed, I bought tickets and hotel rooms and met her there.  Once we met there I noticed immediately that she seemed uncomfortable so I asked her what was wrong.

“I just don’t want you to get the wrong idea on this trip, I just want to be friends.”

“What the fuck, I bought these tickets, is that what your “friends” do?”

“I don’t know, I thought you were just being nice.”

“What?  What did you think we were going to do here, play checkers?  When a guy buys you a plane ticket to Vegas he just wants to be friends?”

“I don’t know, I just wanted to see Vegas.  I’m dating girls now.”

That was a real low point for me.  At least the Vegas gods felt for me and after I ditched her for the craps table all weekend I ended up winning back the cost of the tickets and hotel.  Thank you Vegas, I really needed that.

6.  Trip duration must be relative to how well you know a woman and how good your relationship is. Don’t bring that girl you have only spent one night at a time with on a two week long backpacking trip to Cambodia. It’s better in that situation to have a weekend in New Orleans instead. A good rule of thumb is to always audition a girl with a short trip before inviting her on a longer one. Once you travel with her a little you’ll have a much clearer idea if she’s qualified for a more substantial vacation.

7.  Don’t go to Russia (this is what we call bringing sand to the beach or bringing a sandwich to a picnic). Nothing is worse than going to some place where the chicks are super hot and not even being able to check them out without pissing off your traveling partner. Nothing magnifies your perception of your Western girl’s mediocrity than having hot smart Eastern European girls walking by all day.

8.  Don’t go to someplace super expensive.

9.  Try an outdoors trip. I like the outdoors, but the main problem with a backpack trip is that there are no chicks there. So bring your own.

Charlie Bushmeister

Call me Charlie. I decided to join with others to write this blog because I feel that I have learned a lot about how to succeed in life in general. It took a lot of trial and error and I've developed a wealth of philosophies, skills, and tricks of the trade that would be very useful to like minded guys out there. There's no need to repeat my mistakes, of which I have made many, instead I urge you to read this blog, absorb and practice its lessons, and then go out and have the most awesome life, on your own terms. To me that means good health, success in your career, the number and type of relationships you want, and general satisfaction that you're not wasting your life spinning your wheels, but going forward always towards your goals.

You may also like...

%d bloggers like this: