Question: I'm very attracted to one of my friends/classmates, but I don't know if he/she is gay. How can I find out?
This question came in from several people over the past month, and it's not an easy one to answer. Frankly, when I found myself heavily attracted to one of my friends in high school, I was far too afraid of him finding out I was gay to do more than lust from afar. College taught me a few tricks in this realm, but there isn't really a sure way to find out if someone is gay or not. I'll do my best to give some pointers, but I can't make any promises.
When approaching someone of questionable sexuality, the most important thing is to be honest about your sexuality. If the person in whom you are interested is in fact gay but is afraid of being harassed because of it, they aren't likely to be honest with you unless they feel safe telling you that they may be attracted to members of their own sex. The first part of making them feel safe is by letting them know that you share that attraction. If you yourself are closeted, this means risking letting someone know your identity who may or may not share that identity and who may subject you to harassment because of your sexuality, so be aware of that risk before you start. Approaching someone whose sexuality you don't know is a lot more daunting than approaching someone you know is gay.
While honesty about your sexual preference is important in making your friend see you as a confidant in the matter of his or her sexuality, it is almost equally important to approach your friend in a manner that isn't overly sexual. Remember, just because you are gay and attracted to said person doesn't mean they'll necessarily be attracted to you no matter what their sexuality. Before you can make this person a sexual partner, you first have to become someone they can trust, and if their first image of you is as someone who made a heavy unwanted sexual advance, they're not likely to trust you later. Push your attraction for this person aside and get to know them as a friend first. Once you have a positive relationship with this person established, you can bring up the fact that you think he or she is really cute, but again don't be overbearing in the way you approach your friend on this issue. Hammering the point home again and again will eventually make them feel uncomfortable around you and they'll be more likely to end their relationship with you than accede to your desires.
So, let's say that at this point you've gotten to be fairly good friends with this person. He or she knows you are attracted to members of your sex, but hasn't been forthcoming about his or her own sexual preference. What do you do now? Well, finding some time and space alone with your friend at this point is important. Have them come over to work on some homework together, or go shopping some weekend just the two of you. Again keep it a casual just friends kind of deal--don't make it seem like an invitation for a date. The point of this is to find time alone to talk about things the two of you might not want to talk about around other people. Don't tie your emotions too tightly into this one, your friend may turn you down the first few times you offer some private space. Don't immediately assume that's a rejection of you, and be sure to let them know the offer is open any time should they choose to take it. On the other hand trust your instincts--if it becomes clear that the person wants nothing to do with you apart from a common location or circle of friends, continuing to pursue them is probably an unhealthy decision.
Instinct can work either way for you at this point though. One of my best friends in college was a lesbian who lived in my dorm freshman year. We'd spent a certain amount of time hanging out together talking about our lives and our views on the world, and while I didn't know what her sexuality was at the time, one night I asked her if she wanted to go to one of the meetings of the Lesbian, Bisexual, and Gay Alliance on campus with me. She agreed, and later that night I found out that she indeed was a lesbian. If you've come to the point of knowing that your friend is at least very gay positive, invite them to a meeting of the local gay youth group, to go with you to the local coffeehouse that everyone knows is gay, or to go see a gay themed film. Inviting them into gay space may be what they need to come out to you.
So now that we've gone through all the tips I can give you on approaching someone of questionable sexuality that you find attractive, let's talk about the possible outcomes. The first outcome is that your friend is straight, closeted, or willing to come out to you but not attracted to you. In this case you have a new friend, which is never a bad thing. It's up to you to put a lid on your attraction for this person to maintain that friendship, though, and frankly this will have to start long before you'll have an answer to your question. Always keep in mind that there are other people out there besides the person you are currently pursuing and don't become so singular about your pursuit of this person that you aren't available to take up another opportunity that may come along. It may be that your friend won't realize how attractive you are until you are unavailable, or that you may find your friend isn't nearly as attractive as you thought at first.
The other possibility of course is that you both find each other attractive and decide to become involved in some sexual way. I received email from several people this month asking what they needed to know about safer sex, often in conjunction with the question above. Safer sex in my mind begins with keeping two thoughts in mind at all times. The first is that you can't really know anyone's sexual history accurately because you haven't lived their life, so in order to protect yourself you have to assume they may have something you don't want. The second is to remember that while certainly AIDS is the biggest threat to anyone who is sexually active, there are other sexually transmitted diseases out there that can be equally dangerous. Venereal diseases are generally passed through the exchange of bodily fluids--namely blood, vaginal fluid, and semen, although some like hepatitis can be passed through saliva. Always use a latex condom with a water based lube for anal sex or vaginal penetrative sex, and don't re-use condoms. It's probably safest to avoid cumming inside of your partner as not even condoms are 100% breakproof. In terms of oral sex, the risk of AIDS infection is much lower, but if you want to be on the safe side, use a dental dam (saran wrap works in a pinch) or non lubricated condom, and certainly don't allow your partner to come in your mouth. Real sticklers for safer sex would also say that if you plan on using your fingers or part of your hand to penetrate your partner, you should wear a latex or rubber glove (or fingercots, which are latex sheaths meant to cover a single finger), but frankly I find that to be a little over-cautious. After all, sex is supposed to be fun and spontaneous as well as safe, and constantly having to rummage for a new piece of latex every time you want to touch something gets to be a hassle.
If you want to be 100% safe, there is always the option of avoiding any sort of penetration and concentrate instead on other erotic activities. There has been many a night when I've wished I simply had someone to massage my back and neck or whose back and neck I could massage. Often I think when people think about sex, they think only about oral, vaginal, or anal sex and forget that there are erotic or sensual pleasures to be found in exploring one's partner's whole body. I'd encourage anyone starting out having sex to take the time to explore the whole body and the pleasures involved in each part before getting right down to intercourse. And don't forget about frottage (rubbing your and your partners genitals against each other) or mutual masturbation either. Both activities are completely safe and enjoyable.