The 911 of the week:

I have been planning a trip with a group of friends for some time, and as the date gets closer, people have dropped out, except myself and one of my guys in the group. When it was a big group there was no problem with splitting rooms, but now that it is just he and I, I don’t know if I should go. I have a boyfriend, and I don’t know what he would think about me rooming with a guy for one week. My boyfriend can’t go for work reasons, and I like the friend, should I just bail out or keep the reservations as they are?  

Dear Ms. All inclusive,

Group trips are great, but you might have a better time with a guy friend than you would if there were more opinions on what to do and when. Fun in the sun does not have to be full of sexual tension, in fact the two of you can be good wingmen as long as you can handle being tipsy and cohabiting with some one you kind of like for a week in paradise. The friend should be under no pressure to cancel the trip, it is his vacation too. It could be that you are worried about what your boyfriend thinks because you know in your heart that something might happen given the circumstances. If you are feeling pre-cheating guilt then maybe you should think about why that is, and why you have the boyfriend you do.

This could be a great opportunity to break one relationship off and start a new one with your soon to be roommate. A man can’t help but think about sex when he stays anywhere near a woman, but it doesn’t mean that he will attack you. He will be paying close attention to how you act, and if you want to give him an opening, believe that he might take it. When you get back there are going to be small talk and rumors anyway, so they can either be squashed, or you can earn the water cooler chatter. I think you should let this be an exercise in trust for you and your boyfriend. If something does happen, establish the rules ahead of time and take it to your grave. What happens on vacation needs to stay on vacation. Best of luck, remember that you matter most!


Author of I’m Sorry, You are Not a Pick-Up Artist

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