I'm 28 this year and I have been with my boyfriend for two and half years. Things were little rough in the beginning of our relationship because I have never had a serious boyfriend before and didn't understand how relationships need lots of work. But I think I can see myself with this good man in the long run but now I have doubts…

The problem is, before him, I've only had physical flings and I have never had orgasms with them. I figured it's because things were only physical with those past guys and thought things would improve once I find someone I really truly care about. However, with this current guy, I still haven't experienced and I think it's due to many things: 1. I'm just not that sexual of a person (I do it because I enjoy the intimacy part of it); 2. I haven't found the right man; 3. I don't know if I'm capable of experiencing it due to my pretty conservative Asian/Catholic upbringing. I don't know who to talk to about this, because even with my very close girlfriends, I just don't feel comfortable sharing all this because I feel like there's something wrong with me.

I thought I'd hear from you first before I seek professional help. Thank you so much!
Sincerely, Frustrated.

Oh F, if you could see me right now. I’m all squeamish and sweaty and like, 13 all over again. This may come as a surprise because I’m a pretty vile person, but I have a really hard time talking to people SERIOUSLY about producing fluids. See what I mean? I can barely write this without being a weirdo.
My main problem: “SERIOUS FACE”.
You know that look where a person’s face gets all concentrated and constipated right before they’re about to blow their load. Ugh. Sick. We all have it and let’s face it (pun intended), it’s not attractive. Well at least to me it isn’t. And when people want to get real with me about their sex life, I can’t help but picture their SERIOUS FACE.
I wish I was more mature, more in touch, more free about this subject, but I’m not. However, the reason I wanted to write back is because A) I know how much courage it took you to write to me and B) it’s time for BOTH of us to get a grip.
Let’s start by addressing some of your concerns.

1. “I'm just not that sexual of a person”
Unless you are truly asexual, everyone is sexual. The only difference is to what degree. Some people want to bump nasties three times a day and for others, three times a month is enough. I don’t think one is better or worse. So F, don’t let people make you feel bad for not being some horn-dog – not everyone wants to be Jenna James.

2. ”I haven't found the right man”
Even if you find the RIGHT dude, it doesn’t mean his dick is going to miraculously unlock your sexual dormancy. This stuff takes work, so you’re going to have to put some elbow grease, in this case, lube, into it.

3. ”I don't know if I'm capable of experiencing it due to my pretty conservative Asian/Catholic upbringing”
This is totally NOT true. Believing in God or being a certain ethnicity doesn’t prevent you from having an orgasm. While your religion/background may have played a part in how you think about sex, it doesn’t stop you from physiologically getting your rocks off.

F, both you and I know that I can’t ‘fix’ you, so here’s what has to happen. First, you NEED to start talking with your man about this - he needs to be looped in. So that means saying some things that might embarrass you at first. Touching some things. Switching up the positions. Fiddle with pressures here and there. Basically you need to get down and dirty.

I know, I know, but it’s important. EVERY relationship goes through some sort of adjustment period when it comes to hittin’ the money spot. And F, it’s also important for you to learn how to hit the money spot on YOUR own. No one can do it for you if you can’t do it for yourself. If you still don’t get what I’m talking about – pop in American Pie 1 and watch Natasha Lyonne school Tara Reid.
Now, the next step is to find a good therapist who can get to the root of some of your issues. Bottom line is you need to take care of this mental block in order for it to release the other block, ahem, happening down, you know, there.

Hope this helps and keep me posted. xx

Dear Sasha, I am 20 and my boyfriend is 21. We had been together for over a year when he went and interviewed for and got a job 3,000 miles away, which would start when he graduated from university.

We spent the next several months going back and forth on whether or not we should continue the relationship long-distance. The contract was for 2 years but he wasn’t sure if he’d stay longer and pursue his master’s degree in the same city. Our relationship had been pretty great up until then.

He finally told me that he wanted to stay together for the moment and break up in the summer before he left for his new job. He felt it would be just too difficult with his long hours and the time difference to keep anything meaningful going. There was no way I was going to fall even more in love with the guy and then lose him months later so I broke up with him right after Christmas.

He ended up taking it really badly. He wanted to get back together right away but still maintained his position of breaking up when he left. I kept re-iterating that if he wanted a long-distance relationship and would be back in 2 years I would get back together with him and otherwise no way. He still said no, but wanted to be with me until he left. This went back and forth for months with no resolution.

Now, after all these months he has decided that he wants to get back together, do the long-distance thing and come back in 2 years. If he had said this a while back I would have jumped back into his arms, but now I am going on exchange to another country next year and am not sure if I want to have a boyfriend during this time.

I’m crazy about him and we get along great when we’re not arguing about this. I think we could have a great future and can totally see myself married to him in 5 years or so. He says if I don’t agree to be with him he’s moving away and moving on. I’m so conflicted! Confused

C, here’s the long and short of it: Do YOU.

Look, I know you love your boy but girl, you are so young and this is the time to really live life. To experience what it’s like to be out of your parent’s house, to experience other relationships, and to experience what being an autonomous hard core chick is all about.

Here’s the reality of this situation: if you do decide to stay together, things are gonna get hella complicated. I’ll bet my savings, all $200.00 of it, that one of you will eventually fall off the faithful wagon. Trust. Long distance relationships are hard as f*ck at the best of times, and two years apart is a long ass time, not to mention a long time for people to get up to no good.

C, you’ve also got to ask yourself - why did he so badly want to break up after summer was over? Sure, maybe he wanted to bang some chicks, but more likely than not he wanted to be free from any and all relationship baggage: the calling, the coddling, the effort. Fair enough.

I remember when I was leaving for university the thought of leaving my boyfriend was as dramatic as Alicia Silverstone in the Cryin’ video. He was my world. We even had a pact that if we started dating other people we would always cheat on them with each other. (Chill, we never did)

Cut to my first week on campus – I had already developed a major crush on some boy and was partying like a cast member from The Real World. Soooo, yah.

The point - other than forcing you to watch a RAD Aerosmith video - is that we used each other as safety blankets to get us through the unknown. And C, I can’t help but feel that this is exactly what’s happening between you and your man. Look, I know how comforting it is to have him, but I think some discomfort could do you some good right about now. C, I want you to go away on this exchange and feel some independence, some free-will, and some unabashed FUN! I promise you, you won’t regret it. And if you do, lose my email address.

Dear Sasha,I visited some friends lately in my old hometown and on the same trip bumped into another old friend. I have always considered this person my friend, he’s funny and smart and we used to spend a lot of time together in a group but didn’t really have a close personal friendship. I moved away a year and a half ago and was really excited to meet my old posse again this spring. I contacted this friend and invited him to come and see us all well in advance, I didn’t hear from him but he ended up coming anyways. I was very happy to see him but still a bit miffed that he didn’t respond to the invitation and just showed up. Anyways we agreed to meet the next day (in a group) but he refused to give his phone number (should taken the hint), instead I e-mail him the next day, after all I haven’t seen these people in a long time and was really excited. He doesn’t answer of course. I saw this person again a few weeks back and he totally didn’t even acknowledge the whole incident. I find his behavior incredibly rude and disrespectful but on this latest visit also discovered something else. I reacted really strongly to him physically, like I have feelings for him. Now I have somewhat of a past of liking guys that are unavailable to me and this reaction just freaked me out big time! I don’t really think about him when I’m not around him, I definitely don’t think we’d make a good couple and think his behavior is generally appalling, so why did I react this way? I freaked out so bad, I just couldn’t wait to get away from there and felt totally depressed for days after! I feel like such a mess right now, please shed a little light on my predicament. L

Are you telling me that because he wasn’t ‘nice’ to you, you’re going to get him back by investing fake feelings in him and then turn it around like he rejected you? WHAT?! WHYYYY?! Do you see how this makes zero sense?

L, I get the whole ‘love what you can’t have’ thing. BUT if that ‘what’ is a guy who doesn’t give a sh-t about you, then dang, it’s time to check yourself. And what makes this even more problematic for me is that you just admitted you don’t even like the dude…like, at all.

To top it all off I don’t even think his behavior is all that appalling. Who knows, maybe too much time has gone by and he doesn’t think you guys are all that tight. Maybe he has a girlfriend and doesn’t want to be chatting on the phone with some other girl. That’s all legit if you ask me.

Sure, it sucks that you thought you were coming home to something different but thems the breaks. The last thing you should do is let it mess you up this badly.

L, never give someone you care so little about this much power. Instead, invest your emotions in the friends that did come out, the friends that were excited to see you…you know? And listen up, this part is important: when it comes to men, never seek out the ones who treat you badly. There should never be anything attractive or enticing about that. When someone makes you feel sh-tty about yourself that is not an invitation to let them in further. So please, if there is one thing you take away from this, tell me that you’ll always set your standards high.

I’m leaving you again this week with another song. If Lil’ Wayne is singing songs about how women should learn how to love, then, sh-t females, we REALLY need to get it together.