I’ve been bouncing from one relationship to the next since I started coming to the U of C. Every guy I meet is either hyper-clingy or just isn’t ready to commit. Am I doing something wrong here?
Chris: If you are noticing that pretty much all of the guys you’ve been going out with fit into those two categories, the problem lies with you. You are not being picky enough when choosing men. So, here’s a few things you can do. The next time a guy asks you out, you should ask him up front: “What are you looking to get out of this date?” I know, I know. It seems a little weird and too forward for a first date, or even just an exploratory coffee. But if your relationship investment is in the black, then you need to be a little more shrewd about how you spend your time with potential partners. It’s better to get it out in the beginning than to be led on. On another note, you should probably get a second opinion before you leap into asking this question. Your best friend probably knows your type, so he or she should have some sound advice as to whether this new guy is worth it.
Anna: While Chris has a point, the problem probably isn’t just you. It could also be your environment. I know we’ve all heard the stories about U of C being the place to meet your match, but, quite frankly, it might not be for you. If you find yourself doing the same dance here at U of C, maybe you need to open up your dating pool. The city of Chicago is a big place, and we often forget that in our little academic bubble on the South Side. Maybe you should take a trip to another college campus, a concert, or a museum; you might just meet someone who catches your eye. Maybe the kind of guy you’re looking for is a Loyola or Northwestern guy, or maybe he’s already working. Be open, be patient, and be proactive.
I’ve been thinking about trying something new in the bedroom: anal. The thing is, I haven’t talked about it with my girlfriend because I don’t want to freak her out or think that I’m unsatisfied with what we’ve got right now. How should I bring it up without sounding like a total perv?
Anna: I think it’s great that you’re taking a minute to think before bringing up a sensitive subject like this; it just shows that you really value your relationship. You should start by telling her exactly this—that you thought about her feelings before asking something of her. But before you even bring up the idea, think: What has she said about anal sex in the past? Has she expressed any distaste for the idea? Has she ever brought it up at all? Keep her perspective in mind when thinking about how to bring up the subject.
If she hasn’t talked about it, even in casual conversation, you should take it really slow. Give her the facts, but keep in mind that you want to do this to share something special with her. She is what you desire, and the anal sex would just be a great bonus. If she says it’s not for her, then don’t push it, but do remind her that it’s nothing to be ashamed of. It’s a perfectly normal thing to want, but if you care about your relationship, well, there are other things to get you off.
Chris: This is definitely the kind of subject you need to bring up gradually. You don’t want to skip straight to anal sex, but maybe ask your girlfriend for a little anal play (e.g. touching, stimulation, etc.). When you bring up the idea of anal sex, make it clear to your partner that this new dynamic to your bedroom fun is coming from a desire to explore a little, and not about being fulfilled or “satisfied” in the bedroom. There’s nothing wrong with a little exploration. Though, what you are asking for tends to be a very tricky subject for pretty much everybody. While there is nothing wrong with anal play, it has a tendency to be viewed as dirty or uncomfortable.
I mean, to be honest, gay anal sex is pleasurable because of the existence of the prostate. For women, who obviously don’t have a prostate, their pleasure comes from the stimulation of the wall between the vagina and anus, so don’t get too upset if your girlfriend isn’t up for it. Sex should always be something you are both comfortable with and can enjoy.