Intimate Inquiries

Sometimes, when I engage myself in sexual behavior, I like to wear the clothes of the opposite sex and it turns me on a lot. But the girlfriends that I’ve done this with, and my current one, don’t like it and I was wondering if somehow there is a way to make them more comfortable with it?

Lost on Fantasy Island

Dear LFI,

The only way to get your girlfriend into what you’re into is sitting her down and talking to her about it — you can’t just bust out a sundress and a lacey pink thong without answering some questions. If you can’t get comfortable openly discussing your sexual fantasies with your partner outside the bedroom, there’s no way you’ll both be comfortable with it once you’re there.

There are two things you should do. First, you need to have a conversation with her about what gets you off. Second, while it might not seem all that important to this particular dilemma, you need to ask her what she’s into.

Opening up to her is a great first step, and letting her know that you’re open to testing waters beyond your own comfort zone might help. If she doesn’t toss any curveballs your way the first time, all is not lost. She might just be a little shy about letting loose, so set it aside for now and leave the door open to the possibility. If she starts to share, make sure you’re taking notes.

If you’re not getting anywhere after the first few tries, you might need to start with some baby steps to spice up your sex life — not everyone can jump into cross dressing and role-playing right off the bat.

Instead of asking her to think of ideas herself, take a trip to the book store and hit the “adults only” aisle. Go through a few of the books together and pick one that’s as user-friendly as possible. Make sure you get a range of positions — easy and hard — to work from.

Starting with the simple premise of trying new things will allow you to eventually graduate to more in-depth fantasies.

Happy bumping!

My ex-boyfriend and I broke up about two months ago. We dated for a year, but now all my feelings are starting to come back. I know he still has feelings for me too, but when I told him I missed him, he just kept saying, “we can’t” and “we shouldn’t because we would just fight a lot again and eventually just break up.”

I actually believe it is true, because I’m graduating this year and would move back to Northern California while he’s still here. Also, I know my parents would not approve, knowing the person he is (younger, not Chinese, doesn’t go to UCI, etc). In other words, I’m saying I know there is no future between us, but I miss him so much and he made me really happy.

I miss being with him, talking to him, cuddling and kissing with him. I miss him always being there for me, having someone to depend on. But I know after college, it wouldn’t last. I know the reasonable advice would be to just forget about him now, because going back to him and breaking up again would just be worse, but if he makes me happy, wouldn’t the juice be worth the squeeze?


Dear Juicy,

I’d say your answer hinges on what exactly you’re squeezing.

Take oranges, for example. Squeezing a few of those will pretty easily yield some nice, refreshing orange juice. Pomegranates, on the other hand, are comparatively much more difficult to squeeze and even if you are successful in getting somewhere, drinking straight pomegranate juice isn’t something many people find appealing.

Juices aside, with your relationship, what you’re going to have to seriously consider is whether the effort you put into it is worthwhile. This is not something that you want to jump back into quickly. You might not know it, but you’ve done a lot of work having stayed apart for two months after a break up and returning to the relationship does mean you’re starting over if you break up again.

If you’re being completely honest with yourself when you say that it’s him you miss, and not just the comfort of having a boyfriend, then it just might be worth the effort to work out the issues you guys have had in the past.

It’s possible too that what’s really going on is that, after two months of living the single life, you’ve really begun to notice that you want that consistent support system back and that’s some dangerous ground to be treading.

And, honestly, I’m not sure I buy this whole deal about the breakup being inevitable and I’ve never been a fan of the whole “enjoying it while it lasts” theory. It’s never that simple and it pretty much never works out.

Breakups are a product of two people figuring out that they don’t function well together or that they can’t work out some issue between them. So, thinking that you guys are going to break up down the road should not be the basis of the fate of this relationship. Don’t cite your parents’ disapproval, his age, ethnicity, or his physical distance from you.

First, make sure you have people around you who can help to support you if you need someone to talk to. That’ll help put you on the right track to differentiating him as a person from the role he played in your life.

Then, look at the relationship from the perspective of the here and the now. If you really are constantly fighting, then it’s a bit like trying to get a cup of juice from that pomegranate — it becomes way more effort than it’s worth. You need to sit yourself down and consider whether you think the two of you can put an end to the fights.

This isn’t something your friends or your parents can decide for you and their opinions certainly shouldn’t be the basis for whether you view him as a long-term option. You need to deal with the here and the now before you factor in the future — and after that, you might just find yourself having that long-term “breakup or stay-together” choice decided for you.

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