Miss Information

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A closeted guy told me he wanted to experiment with me. How should I proceed?

by Cait Robinson

Have a question? Email Letters may be edited for length, content, and clarity.

Dear Miss Information,

On New Year's Eve, I met a closeted bisexual guy in his thirties who told me that he wanted to try fucking a guy. As a twenty-something gay guy myself, this is a fantasy realized. What is the best way to navigate the situation? Should we discuss beforehand what he's comfortable doing? I'm quite a sexual person and would love to be able to play out some fantasies on a newbie. But I don't want to get into this situation and have him to freak out when it comes down to having sex. When we kissed on New Year's Eve, it was the first time he'd done anything sexual with another guy, and he was very keen. What to do?

— Un-Closeter

Dear Un-Closeter,

I love that you are taking this guy's sanity into account, even if it's just for the sake of fulfilling your fantasy. It's a responsible and generous approach, and one we should all take with our partners, no matter how experienced.

It's a great idea to talk to him first to get a sense of what he expects/wants. You can also keep your antennas out for any hint of weirdness (i.e. any hesitation, nervousness, Republican senatorial affiliations, etc.). Better plans are laid while the clothes are on. This way, by the time you get into a dark room, you know he wants to be there and he knows you're looking out for him. That kind of trust will reap dividends. 

When you're in the moment, keep an eye on him. You don't need to ask if he's okay every ten seconds, but get consent before anything big, and keep communication lines open and light throughout. Also stay tuned in to nonverbal cues. If you are afraid of overstepping bounds, let him take some agency: put yourselves partway into a position, then let him take the initiative on the last bit. You also may want to arrange a "safeword" if you don't think the standard "ow" or "wait, stop" will work.

Before you go in, be clear on how you will react if he panics, backs out, or otherwise seems hesitant. This possibility may be remote, but it is nonetheless a possibility. If he chickens out — explicitly or implicitly — it's game over. Under no circumstances should anybody be wheedled into a sexual act they are not prepared for, period. If you think it will be hard for you to respect this, or that the temptation to whine/beg/plead will be too strong, do both of you a favor and bow out now. Otherwise, you run the risk of being both his first and his last.  

Dear Miss Information,

I'm twenty-years old, and currently in a long-distance relationship with my twenty-two-year-old boyfriend. I feel the need to elaborate on "long distance." We met two years ago. At the time, he was living only an hour away, finishing his last couple months of college. Once he graduated, he had to move back home to south Florida. At first, it wasn't that much of a problem. We got to see each other for a week or so every three months; some people aren't that lucky. A little time together is better than none at all. 

But now I'm moving a couple miles north of my current location to start college. This will put us at a total of 294 miles apart. To solve both the issue of distance, and the fact that I really could use a roommate to help with bills, I asked my boyfriend — even though I knew the answer — if he would move in with me. As I expected, he said that he couldn't because he needed to fix his broken car, and find a job to pay loans. This I understood and accepted, even though I was really unhappy with the answer. 

Instead of getting any job that will pay money, just to get him started until he could get he job he really wants, he has teamed up with his best friend, who also went to college for something similar. He's aiming higher and is chasing only his desired career (which is great, don't get me wrong). Waiting for him to get a job, pay off his loans, then get enough money to move will take a long time as it is. 

I don't see why he couldn't start that here with me. I would be willing to help him move — even pay every bill myself until he could find a job. Lately I just feel second to his career and less important in his life. It feels like it'll be years before he is ready to move in with me. I know he isn't blowing me off, because he never wants to leave when it's time for him to go home and we both cry every time. I almost snapped not too long ago from the weight of distance once before, and he saved our relationship. No one who wants to blow you off would bother with that. 

I feel that I'm being selfish. I want him, but at the same time I don't ever want to stand in the way of his dream. Is it wrong of me to want him to put the dream on hold for just a little while? Would it be bitchy of me to give him a choice: "It's either me or your company?" I want no one but him, but I just don't understand why can't he chase his dream here, with me. 

— Too Selfish for Love

Dear Too Selfish, 

When you graduate from college in this economy, your options are basically "marry rich," "nepotism," or "Artificial Flower Factory." Until you do it yourself, it's hard to understand the peculiar cocktail that is post-graduation. Your frustration is understandable, but you have to let your boyfriend put down his roots right now. The years immediately following college are, for many, more important to who they become than the years they spent in college.

Though "boyfriend = roommate" seems like an attractive option, no jump in commitment should ever be borne of economic interests. ("Let's have a kid so we qualify for those sweet food stamps!") If you need a roommate, go through your university or your friends, or hit up Craigslist. Pulling your boyfriend close at the expense of his stability, while you're both on unstable ground, couldn't possibly end well. 

You're right, though: it may be a long time before you two are in the same place. Being geographically tethered by college and/or unemployability is just one of the things that sucks about being young. But "living together" and "stuck apart" are not your only options. There's a whole range in between to explore, so enlist your boyfriend and make a plan. Schedule some visits in advance, and, if he has flexibility with his self-made job, see if he can crash with you for extended periods. Ask him what his vision is for this company he's starting, and see if he has plans to take it away from Florida in the long-term. Enjoy him when you see him, and throw yourself into your own life when you don't. 

This isn't a rooting and growing time for him alone — you're in a big transition phase too, and you'd do well to commit as best as you can to your education and what you hope to gain from school. Ideally, you'll become more settled in your academic life, he'll have some traction in his career, and then you guys can meet in the middle — no compromised dreams required.