Q: I want to try anal sex with my girlfriend but I’m not sure how to ask her because I don’t want her to get mad or upset with me. It’s just something I want to try, so what should I do? -Curious

CHICK: My advice on this “intimate matter” really depends on how long you’ve been with your girlfriend or how comfortable you two are with each other. Have you ever tried anything else more risqu? in the bedroom? Assuming that this is your first request and that you two are relatively comfortable with each other, then the best thing to do is mention anal sex in an offhand way and watch for her reaction. Tell her some friends of yours have tried it and enjoyed it, so would she ever be interested? Or you could just begin a general conversation on the different things you’d like to try in bed. Ask her first if she has any special fantasies or secret wishes that she’d like to fulfill or act out. Then listen with the same amount of respect that you’d like her to have when it’s your turn to divulge. If you’re still a little shy about broaching the subject, begin this conversation when you guys are in an intimate environment, like spooning after sex or during foreplay. Both of you will be more in the mood and more open to discuss and try new things. And if she isn’t necessarily eager to try anal sex now, who isn’t to say that she won’t be at some point in the future? In the meantime, maybe there’s something else that you’d like to do that she’d be willing to try.

DICK: Honestly, you really want to try anal? It doesn’t do it for me, but whatever floats your boat. Your lady friend might not take to kindly to it. My first suggestion is don’t say “I hear it feels really good because its tight.” That would be implying she is used goods, and last time I checked the girls don’t take too fondly to that. Is the sex that bad that you feel the need to switch it up and be a butt pirate? I hope you know your girlfriend well enough to know if this is out of the question. Is she freaky? Does she like crazy stuff? But most importantly does she have a nice butt? From what I imagine it would be very important to make the butt sex good. Just remember regular sex is better than trying for butt sex, getting turned down, and having to wank it.

Q: How do you act around a friend you mistakenly (and drunkenly) hooked up with? I’ve always had this crush on one of my good guy pals and recently acted on it at a party when we both had been drinking for a while. But now I have no idea how he feels about this whole thing. It’s awkward because we still are friends and all of our friends are friends with each other and so I’m always bumping into him. What do you suggest I do? ~Feeling Awkward

CHICK: Don’t turn this into one of those “elephant in the room” situations, when your little drunken episode is never discussed and just sits there, big and awkward, like an elephant in your dorm room. The best thing you can do is to address the issue ASAP, keeping the conversation as light as possible, however serious you might feel. This way you can gauge his emotions better. Give a little laugh and crack a joke about how crazy you two were that night, and see how he responds. Does he cringe? Does he just smile and laugh? Does he blush? Does he look horrified? Then tailor the rest of what you say according to how he reacts. And as elementary as this might sound, it doesn’t hurt if you can scope out his opinion of that night from mutual friends (someone you can trust, of course) beforehand. The goal of this conversation is NOT for you to feel rejected and crushed, but to clear the air about what happened and see if things can evolve into something more than a friendship. If he still considers you as just a friend, and that night as a mistake, then by all means, call your girlfriends over, indulge in a pint of Ben and Jerry’s, vent and wake up the next morning ready to move on. If, however, he’s game to start something, then look slyly over at him and ask if he’d like to continue where you two left off that night sans alcohol and give yourself a little pat on the back.

DICK: I guarantee he is at least somewhat happy. Guys like hook ups, and friends with benefits are the best. Especially now that it is getting cold and people need someone to keep them warm. My suggestion is don’t feel awkward and just make a move when you’re both drunk again. The key is don’t act differently. If he wants something sober, he would let you know. Plus he is a dude and most of the times they can get it for free. So if you actually want another hook-up, do as Foxxy Brown says and “put your ass into it.”