So, the other day I was helping my girlfriend get her digital music collection backed up on a hard drive, better organized and updated.  I was using her computer and her iTunes to get everything set up, and at one point, I opened the video tab to find, to my surprise, a few porn clips on there.  I didn't play any of them, but could tell from the image frame these weren't Cinemax Red Shoe Diaries soft-core. 

We have a pretty happy and active sex life, though she was pretty inexperienced before we met.  And we've even pushed a few boundaries with "racy" texts and photos while separated by travel and a couple of, let's say, more daring escapades.  But the subject of porn has never been brought up in any kind of remotely serious manner (or non-serious for that matter). Now, I don't know for a fact that she downloaded those clips (or has even watched them), but I'm not sure how else they would've gotten there.  And though I wasn't snooping when I stumbled upon them, I didn't want to draw attention to them, nor am I sure I should do so now. But the idea of watching porn with her is an intriguing one (not that I'm a porn connoisseur myself; I don't have any downloaded on my computer), and this has certainly piqued my curiosity. 

I know guys probably ask all the time, "How do I get my girl to watch porn with me?" but that's the backstory to my asking.  And I'm interested as much for her pleasure as mine.  So, should I mention the clips I found?  Not mention them and just straight out suggest watching some one day?  Let sleeping dogs lie?  And if and when we do make the leap, where's a good place to start (assuming she doesn't already have a stash and has just been waiting for me to ask)?



Could Be on to Something

Honestly, my knowledge of technology is pretty limited, CBOTS, so I have no idea whether or not you would accidentally get porn shoved into your iTunes account. I see two possibilities here: either your girlfriend has no idea that the porn is on her computer, in which case she would probably want to know and get rid of it and figure out how to block it from getting there in the future; or she downloaded it and she knows it’s there, and she wanted you to find it. Either way I think you’re safe bringing it up to her. I think your best bet is to just ask her where she wants it stored—“Do you want a separate porn folder? Do you want this to download onto your phone, or is it just for computer use?”—and see how she reacts. If she’s embarrassed, tell her you’re kind of intrigued and turned on, and you might want to watch it with her. If she’s upset and grossed out, well, then you have your answer. Delete it and move on.

I am a 30-year old straight girl who just got out of a six-year relationship. It has been almost six months, and even though it has been a big adjustment (he broke it off and I was totally shocked), I have been enjoying rediscovering myself. I am living on my own for the first time, I started a new job that I hope will end up being a new career, and I hope to be ready to start dating again soon. Last week I was traveling on business with my new bosses and one of our clients. It was a great time and an excellent learning experience. We bonded in a way that we couldn’t have done any other way. They are like my big brothers now. During this trip, I met a guy that the company does some business with. He was charming and attractive, and he made it very clear almost as soon as we met that he was interested in me on a more personal level. After dinner, we all went out for drinks. It was obvious to everyone what was going on. I was definitely flattered, slightly intrigued, and very conflicted. My bosses were joking about it afterward, and they didn’t seem to care much either way. Our client, who is a good friend of my boss, was telling me that I was an idiot and that I missed the boat. The guy wanted me to join him for another drink after everyone else was turning in, but I begged off, claiming jet lag and exhaustion (both true). He told me he was “smitten.”

This is a guy who lives very far away, with whom the company does business on a regular basis, but who I will likely not see more than once or twice a year. He relies on us for his business and not vice-versa, so I feel that there is little chance that anything that happens between us would damage the working relationship. And yet… I don’t know. He will be coming to our city on business in two weeks, and I will be in charge of showing him around and taking him to meet other clients, etc. He asked me if we could have dinner while he was in town, and I said yes, of course, but now I don’t know where to draw the line. I’m not really a one-night stand type of girl, and I know this is not a relationship that would or could ever happen, but part of me wants to just have the fling when he comes here. What do you think?

Not (Usually) That Kind of Girl

If you really think that your bosses won’t care, then I say go for it. You have already shown some restraint, you have already been professional, and you seem to have weighed all the pros and cons. You got through the business trip in everyone’s good graces and an obviously important client and friend of the company was cheering you on. It sounds to me like you’re in a good place. Do make sure to put all your cards on the table ahead of time. Tell this guy that you don’t want anything to interfere with your working relationship, that you’re not interested in anything serious, etc., etc. You don’t want to hurt him. Then, if the chemistry is still right, have at it and have fun. It will probably do you some good.