Dear Jackson,

I have started dating this girl who I really like, but there is something about me she doesn’t know. I told her that I live in Cambodia “exploring businesses opportunities,” which is half true. What she doesn’t know, however, is that my business involves remotely running an affiliate website for gay pornography. I don’t actually produce porn, which is made in Thailand, I just collect commission from other porn sites every time someone goes to my website and clicks on a link. I’m afraid that if I tell her what I do, she’ll think I’m gay, or that she will find it objectionable somehow. How do I broach the subject in the most benign way possible?

I knew a couple of guys in college who starred in solo webcam shows. They were all straight and their audience was predominantly gay, which they didn’t mind – after all, they were making $50/hour to masturbate… something they would be doing anyway. Still, when girls found out, they were generally turned off by these guys’ part-time jobs.  Why? Because it hinted at a type of exhibitionism and promiscuity that is at odds with traditional monogamous relationships.

You need to be prepared for her to run. Having said that, it sounds like the relationship is fairly new – openness could be your means of salvation.

Broach the topic lightly. Ask her what she thinks of pornography. Most couples have this conversation at some point. A good lighthearted question to start with could be: “You know, a lot of guys like watching lesbian porn. I’m not sure why ... But do women get off on seeing men go at it?” Gauge her reaction. Some women are stringently anti-porn, and they have every reason to be.

Once you start the porn conversation, you need to ease towards your goal. Perhaps talking about it in a bar would be good – it will show that you’re comfortable with what you do. Mention your other business ventures, if you have them. Then slip in, “I also run an affiliate website for gay pornography.” Your girlfriend will likely be shocked at first. Explain what it is you do. Assuring her that it’s 100 per cent gay might ease any misgivings she has about porn − gay porn tends to be more egalitarian than its straight cousin – but it will also make her question your sexuality. If you do get off on the stuff, be open about it. Who knows . . . she might be into bringing another man into the bedroom. If not, you should be ready to tell her exactly how and why you got into this business. Tell her why you still do it. Sharing how much money you make might help. She’ll probably want to see the website. Expect for her to judge you based on its content. If the stuff is raunchy, you’re probably doomed. If it’s porn with passion, you might be OK.

If she still finds this all objectionable, you need to decide if this woman is worth giving up your business venture. That, however, might not be enough – the fact that you were even once involved in the gay porn world will likely send her running. If you love her, however, it’s worth trying … If you don’t, or if it doesn’t work out, don’t fret – I’m sure there’s a more open-minded woman out there waiting for you. Have you ever tried picking up a girl at a gay bar?

But one more thing: If you’re going to be living in Cambodia, make sure you’re aware of the country’s stringent anti-pornography laws.

Got a question about sex or relationships for Jackson? Email [email protected].