I am a 27-year-old straight female in a monogamous relationship with a 33-year-old straight male. We both adore you and love your show. We have been in a relationship for almost three years now, living together for two years. We have a very healthy, adventurous, and fulfilling relationship, and travel a great deal together and apart. We are both very supportive of one another and encourage each others independence.

Here's the issue. My boyfriend was offered the trip of a lifetime by a friend, which entailed purchasing a Unimog (an all terrain vehicle made by Mercedes) and driving it from Denmark to Mongolia over four months. He asked me if I was okay with him going on this trip. Of course I said yes. I want him to be happy and I want to be supportive. There was no doubt in either of our minds that we were going to stay together through this. I am also visiting him twice on this trip for three weeks each time. I have a couple more weeks until I see him, and I am counting down the days.

The problem is the guy he is on the trip with is very difficult to deal with, a misogynist, an asshole, selfish, etc., who has very much made this trip into a guys only Euro vacation of drunken debauchery. I got upset when I Skyped with my boyfriend today because I asked what they had been doing in Prague for the last few days, and he responded getting drunk and hanging out at a pool. I was up front that I was annoyed by this, because I am taking care of both of our lives and our dogs while he is gone which has been very tiresome, and I was hoping that this was more of a "cultural enlightenment" trip. My boyfriend and his friend are both avid hikers and mountain climbers, so I figured they would be doing a lot of thrill seeking activities and hitting museums, temples, etc. This hasn't been the case. I'm trying not to get upset, but it's really difficult at this point. My boyfriend accused me of being insecure and jealous and told me I needed to talk to someone about it. I wrote him an email after our conversation to let him know that this was not the case. At this point I'm just annoyed because I keep hearing about how they are hitting every European red light district and getting shit-faced.

Here's a little bit of a background as to why he jumped to the insecurity conclusion. My boyfriend is the most attractive and most confident guy I have ever been with. I have always dated guys that were far below me physically, so this has been a difficult thing to get over. I've actually had random strangers come up to me and tell me "good for you." I assure you I am no troll. I was raised by wonderful parents and brought up to be a secure, confident young woman. Unfortunately, I was in two relationships with very jealous and abusive guys (verbally and physically) and this is my first "healthy" LTR. Needless to say, I have gotten annoyed in the past with all the swooning over my boyfriend. I feel like it is a direct result of my past relationships given that I never felt an ounce of jealousy in relationships prior. I trust him, but not completely, because there's a part of me that wants to protect myself from getting hurt. We have both gotten jealous in the past, mine has just been more frequent and I of course agreed to work on it because I very well know a relationship cannot sustain itself without trust. He has been really great about getting me to vocalize when I feel insecure. It's just simply stating, "Hey, babe, I'm having an insecure moment, please reassure me that such and such is not the case..." which has worked really well. The other piece of this insecurity puzzle is his past. He was a cheater for a good part of his early twenties and is also a very good liar.

I want to trust him completely, Dan. I have come a long way and I know there are plenty of people that could not deal with my current situation. Listening to your podcast has helped in so many ways. Any advice you can give me would be wonderful. I really respect you and value your opinion.

Girl Left Behind

My response after the jump...

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Your boyfriend is on an epic road trip for the next four months, GLB, but you're going to join him on the road twice, for three weeks each time, before it's over. That means you're only going to be apart for ten weeks total. That's two-and-a-half months, not four.

So try to chill the fuck out.

Okay, okay: your boyfriend is swoon-inducing beautiful—or so you claim (I usually require pics when someone makes a claim like that, GLB, but I'm making an exception because you're a fan)—and you're naturally worried about Czech sluts throwing themselves at him, to say nothing of the the bad influence of his shitty, shitty friend and those twin inhibition demolishers, booze and distance. Those are all legit concerns. But you can't give the boyfriend your blessing to go off on an adventure and then blow up at him for not having precisely the sort of adventure you assumed he would be having.

Moving on...

Immediately after explaining to me via email that you're not being insecure—which you did immediately after explaining to your boyfriend via email that you're not being insecure—you go on detail all the good reasons have you to feel insecure. The cheating in his past relationships, the likelihood that Czech sluts are throwing themselves at him (swoon-inducing beauty), the fact that he's a very good liar. Your feelings of insecurity, given the circumstances and the history, are entirely reasonable. It's not too much to ask your boyfriend to begin your Skype sessions by rattling off the same sorts of reassurances he does at home: "Hey, babe, we're doing a lot of partying but I'm not messing around with anyone else—and I can't wait to see you."

Finally, GLB, I want to draw your attention to one particular sentence in your long, long letter: "At this point I'm just annoyed because I keep hearing about how they are hitting every European red light district and getting shit-faced." That's what we in the advice biz call "a solvable problem." And here's how you solve it: After your swoon-inducing boyfriend is done reassuring you about his faithfulness, GLB, tell him to shut the fuck up about the drinking and the red-light districts and the pool parties. Since hearing about the partying feeds your insecurities, talk about other shit when you Skype.

And remember—finally, finally—that your boyfriend and his shitty, shitty friend will be leaving Western Europe soon enough. Soon they'll be leaving Europe altogether. They're going to find fewer red-light districts to hit—and fewer pool parties to attend and fewer Czech sluts to fend off—as they make their way from Czech Republic to Slovakia and into Motherfucking Russia. By the time they hit Kazakhstan, GLB, there won't be any of red-light districts for them to enjoy or for you to worry about.