Q This might sound sick, but I have a bad crush on the dad of one of my best friends. He’s pretty good looking for an older dude and a lot of us would tease her that her dad was hot when we were in high school, but it never crossed my mind to do anything with him. Now that I am 21, it’s like, why not? I’m more than legal, and he’s a free man (her parents have been divorced since she was a kid). It’s not like I want to be my friend’s stepmom or anything freaky like that. It’s more that I’m thinking it would be hot to fool around with him. Is that really, really bad? Would it ruin my friendship if I did that? I mean, I would try to hide it from her, but if she found out, would it ruin it, do you think? Is it even her business?

A Technically, as long as the sex is legal and not in someone’s face (or front lawn), then whom you have sex with is not necessarily anyone’s business except that of the two (or more) people involved. But life rarely runs on technicalities, so I’d encourage you to think more deeply about your desires. On the upside, you and her dad might have fun. You might have one or more pleasurable sexual experiences together, and you may even decide you like him as more than just a “friend’s-dad-with-benefits.” (Except maybe that would be a problem, as you said you don’t want anything serious with him.) On the downside, her dad might reject you, or you two might have an awkward sexual experience, particularly if you have very high expectations or he has sexual problems associated with aging or other issues, and that may make things feel weird between you and him. Keeping this information from your friend may make you feel dishonest (though that dishonesty might excite you, but if it does, I’d encourage spending some time thinking about that). Her dad might have such a great time with you that he wants to spend more time with you (even if just in bed), and if you truly don’t want much to do with him, that may be a tough line to walk, particularly if you lack experience communicating about what you do or don’t want in relationships. Then there’s the issue of your friend and her dad. While I understand your concerns about ruining your friendship (and yes, that’s a possibility), it is also possible that your friend’s relationship with her dad might be strained or seriously damaged because of your dalliance. She might feel as if her trust has been betrayed by those closest to her. So while wanting to be sexual with someone who may seem off-limits may feel hot, I think it’s wise of you to think before you pounce. Sometimes, people (of legal age) do have sneaky sex with their friend’s mom or dad; other times, even when they feel attracted to that person, they decide the idea is better left in fantasyland. In fact, some of the hottest chemistry is between two people who want sex but never indulge. If you do decide to go for her dad, I’d suggest talking things over with him to be clear about your boundaries, your feelings for each other, your expectations for your involvement, and your plans for being caring of and respectful of the fact that his daughter is your close friend.

Q I’m a lesbian who has been out for many years. Since late college, I have only dated and slept with other women. Lately I became curious about a regular at a (non-dyke) neighborhood bar I go to—a GUY! I am really femme, and most people don’t even know I am into women unless I tell them. The other night I went home with him and had sex—my first guy since college. I am still crazy sexually attracted to women, but this guy was different. I know I haven’t “turned” straight—but is it weird to want men now? I have always been a loud, proud lesbian—now I’m not sure what this makes me, and I feel as if I can’t tell anybody what happened.

A Dr. Alfred Kinsey and his research team interviewed thousands of women and men in the first half of the century, and what they heard caused them to suggest that people’s sexuality might, to some degree, be fluid—particularly if one doesn’t allow social conventions to constrict one’s behavior. Most people find that their sexual likes (e.g., preferred frequency, types of sex acts, preferred positions, body type they feel attracted to, etc.) change throughout their lifetime and, for some people, this includes the gender of potential partners, too. That said, your concerns are shared by many women and men who identify as straight or gay and then suddenly find themselves eyeing someone of the “wrong” gender. But there’s also an openness to people (regardless of gender) that I’m hearing from you, and that’s something many people try for years to cultivate. Go, you. As to whether you want to open up and tell friends: If you do, you may find that at least one or two friends (lesbian, gay or straight) have had similar experiences—or fantasies—too.

Q My girlfriend and I are in our midtwenties and have been together for almost a year. We have a pretty decent sex life, I guess. But it’s bland. There are all these things that I want to do with her, but she doesn’t want to do them with me. I’ve been wanting to try anal forever, but she won’t let me. That’s probably the biggest one, but I also want to come on her face, and she won’t let me do that, either. She lets me come in her mouth every now and then—but that is about it. There are four or five positions that we do. It seems like, for our ages, we should be doing a lot more than we are doing. I was a weasly runt up through college and got a late start at dating, so I have a lot of catching up to do! How can I get her to see my side of things?

A It’s natural to have fantasies about exploring. It’s also wise that you’re talking to your partner about your wishes, rather than just squirting your ejaculate wherever you want. So here’s the deal: Although it may seem as though every young person is doing everything imaginable—and liking it—that’s just not true. Although the majority of twentysomethings have had vaginal intercourse, and a lot have had oral sex, it is the minority—roughly 20 percent—who have even tried anal sex. And of those who have tried it, fewer do it regularly. So while it may seem as if “everybody is doing it,” everybody actually isn’t. Even if everyone were doing a particular sex act, it still wouldn’t mean your girlfriend should. Becoming sexually experienced may seem as though it is all about trying new positions and places to drop your semen, but it’s actually much more than that. Becoming “good” at sex also involves communication (talking as well as listening), being open to new things (but not forcing others) and being caring of oneself and one another. If you truly desire sex acts that she’s not into—and you won’t rest until you get them—then it may be that this relationship is not for you. It’s okay to be honest with your girlfriend and let her know that, so long as you don’t blame her. It just may be that this relationship doesn’t meet your current needs. You also might check out The Guide to Getting It On! (Goofy Foot Press, $23.95) for both sex tips and helpful advice on communication.

Send letters to Debby Herbenick, Ph.D. c/o Time Out Chicago, 247 South State Street, 17th floor, Chicago, IL 60604, or send e-mail to inandout@timeoutchicago.com