Transitioning Woes and Dating Safety

Question: Hi, I know what I’m planning is illegal but I have to ask someone. I understand you no way encourage this activity but hypothetically speaking. I’m pondering on changing genders (MTF) and while I get my life in order, I have a need for money. My low paying work isn’t going to cover my expenses and while I only currently crossdress, I have noticed quite a fanclub on a few dating sites i frequent. I haven’t met anyone yet(as a female)but I have been offered cash for sex numerous times. If,no certainty yet, I decide to take men up on these requests, what safety issues should i make mandatory for sexual partners? Testing, meeting locations, personal safety issues i maybe overlooking? Time to convince me it’s a bad idea:(

Answer: There are tons of sites out there that discuss sex work in ways that are empowering to women. I am not certain of any that are particular to transwomen or cross-dressing, but these websites will likely give you a good starting place in understanding what someone who does do this might experience.

As this is a subject I don’t know much about, I am not sure which websites are well-regarded within this community of women. It’s not really something that is currently under the umbrella of my knowledge. I did type “sex worker safety” and “sex worker resources” into google and got a variety of results that looked to be helpful. I would recommend if you are curious about studying up on sex workers rights and general women’s safety that you read some of these sites.

I would also recommend that you search for websites that discuss this specific to your local area. Remember laws surrounding these things vary from place to place.

For general information and starting points I visited the sex workers rights wiki page (here). If anyone can recommend a website that they feel would be useful, or if you are more involved with sex workers rights and health/safety than I am, please leave a comment.

I would like to focus more on your health, happiness, and safety. I would put a big hold on this and, if you haven’t already, seek out local resources for transitioning. From your question, it seems as though this is a matter of money. For many, this does seem to be the best option for them, or an option that they genuinely want to explore. See if there is someone you can talk about all of this with who knows what you are going through and may be able to offer more assistance. Again, I don’t know where you live, so that makes this more difficult in finding you help.

When I searched for my area I found a school page that provided a lot of helpful links (transgender resources) – as an example.

As for general dating safety, here are some of my go to tips. It’s by no means a comprehensive list. They are things I kept in mind not only for dating but spending time with people I don’t know very well in general.

1. Talk to someone prior to meeting them. On the phone and in written form. If something feels off about them, don’t meet them. Gut instinct is important.

2. If something feels off when you do meet face to face, understand you are not obligated to continue the date. Continue to follow your gut.

3. Always meet somewhere public where other people will be around. Somewhere well lit is a good idea.

4. Tell someone where you’ll be and when you’ll be there, and check in throughout the evening.

5. Get tested regularly and, best case, ask for a print of their latest checkup. It’s also helpful to get a feel for how they care for themselves (do they have good hygiene? when they talk about sexual health do they use responsible language? do they always practice safer sex?) It’s not a surefire way to prevent the spread of infection but you probably already know that there is no way to be 110% safe.

Best of luck to you on your journey and I hope you’re able to find the help that you need!

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Question: Conservative Exploring Casual?

Hi! A friend of mine recommended I ask your advice on a topic. I’m a 32 year old man, and have lived a very conservative life due to my religious beliefs. I was a follower of waiting until marriage until very recently. I’m in the process of re-examining a lot of things about what I want and believe. A short time ago, a woman brought up the possibility of a FWB scenario. This isn’t the first time, but previously there was a combination of moral doubt combined with the knowledge that the women in question really wanted more than I did, and I knew it would be using them to take them up on it. However, this new girl has caught me at a time when I’m questioning my old moral position, and further I don’t think she actually wants more than sex. Consequently, I’m giving serious thought to the offer. One thing I’m not certain of though is the idea of separating emotional intimacy from sex. My lack of experience means that I have only had one previous partner, and I already had an emotional connection before we took that step. I know I can’t really tell whether I’m emotionally capable of casual sex until I actually try it, but are there any indicators that might give me some hints? Thanks so much for your advice!

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Well thank you for your question, and welcome to the blog! It’s nice to have you. The first thing I would like to point out, which may help ease some concerns you have, is that it definitely does not sound like you are using your lady friend.

You mentioned that she may want more, but that you think she is comfortable with just having casual sex. If this is the case, let her be that free thinking lady that she is and trust her. You’re two adults looking to connect and explore and it’s okay to have hesitations as long as you’re both consenting.

A healthy FWB relationship will have open lines of communication and mutual respect for one another’s situation.For instance, you’ll talk about boundaries at the start. What’s on the table, what’s off the table? Will you see each other once, or semi-regularly? Will you be dating other people? How will you handle safety? If one begins to develop feelings for the other that cannot be held within a FWB relationship, how will you approach this conversation together?

You don’t have to have all these conversations at once but it can be helpful to know that they are there when you need them.

How do you know if you can handle it? Oh, boy. The big one for me is finding that sweet spot where you can still experience intimacy with your partner even if your relationship is casual. Do you enjoy this persons company? Do you find them to be a lovely human being? Certainly that will reflect itself in the sexual experiences you have with one another. You can have intimacy without having a relationship. You can have intimacy without falling in love. I would actually not advise a FWB relationship without a certain level of chemistry. Sex with someone you’re not attracted to, sex with someone you don’t find interesting, sex with someone you don’t click with, it all sounds like a recipe for a bad time. Chemistry does not necessarily mean that a relationship will progress to the kinds of intimacy more well marked by long-term relationships. Sometimes chemistry is just a fling with a trusty friend.

Aside from the issues of intimacy, make sure you know that casual sex doesn’t necessarily mean sex stripped of all meaning, emotion, feeling, and power. Casual sex is incredibly powerful and is carelessly tossed all too frequently into the smut pile. You get to make the experience what you want it to be.

Before I sign off, ask yourself these questions:

1. Do my friend and I want the same experience?

2. Do I feel that I can trust this person to be honest with me?

3. Do I feel excited about this and feel as though it will be a fun experience?

Disclaimer: There can certainly be a lot that doesn’t go right in a FWB relationship. But the same goes for every kind of relationship. Focus on what you can control now, and handle potential bumps as they come at you.

That should, I hope, get you started.

Do you have a question about sex or love? Submit to the top by hitting ask advice and I’ll answer it on my blog.

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Art of Seduction

I was wondering if you ever read The Art of Seduction by Robert Greene and what your thoughts are on ideas in the book.

I haven’t read that book so I’m not familiar with what it discusses regarding seduction. I pass by it ever now and then and always think I ought to buy it but haven’t yet. It’s one of those books I’ll need to read with a notebook and a pen which, during senior year, takes second place to my trashy cool-down novels.

Going off The Art of Seduction and the idea of seduction. I took a great class a few years ago called Nonverbal Communication. A lot of what was included in the class was emotional intelligence. Little things people take for granted that help make things like dating so much easier. I don’t like to think of seduction as playing a game, working someone over, or beating some imaginary odds that were never really there to begin with.

I like to think that seduction is just understanding how your body is being read by the people around you. That can involve little things like eye contact, body positioning, the colors and kinds of clothing that you wear, tone and attitude, smell and hygiene. Lots of nonverbal cues.

This is why people who don’t dress for their body type, don’t take care of themselves hygienically, and go into a date with the idea that they deserve to be loved but pissed off that no one loves them are probably going to have a bad time.


I don’t believe that seduction is necessarily something we actively do. When you find someone that you like, that you feel a connection with, a lot of the seduction goes into autopilot. Your cheeks might flush, you may lean in towards them when you talk, you might make the effort to dress more nicely.

Some people make the mistake of over-seducing by trying to play the games. Some people make the mistake of reading into these simple cues that sometimes don’t mean shit. For instance, a smile could mean the person likes you, but it could also mean they are being polite and want you to go away.

My problem with the game is that it assumes that if you do something right, you’ll win the prize. Sometimes there’s just no right combination, it’s just that the people aren’t right.

If you really want to practice the art of seduction (which now I suppose I ought to read) I would recommend:

1. Love yourself.

2. Acknowledge that you are worth being loved.

3. Acknowledge that it doesn’t mean you are entitled to the love of others.

4. Remove the pressure from playing a game and attempt to just let the moment be what it is.

5. If you like someone, focus on the subtleties of being around them. Smiles, eye contact, honest conversation.

When you like someone, let it grow inside of you. Separate the small lusts from the bigger crushes. And when you like someone, tell them. That is the most important part. Ask them out. If they decline, they decline. Perhaps the moment wasn’t right. Maybe they’re not the one for you. The hardest part of the whole seduction concept is that we might not get the things that we want the most.

That’s fucking life.

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Cohabitation: Our Response Post!

J & I present to you, our responses to your cohabitation questions.

A big thank you to everyone who took the time to submit. It is fun to write a more personal post now and then and to focus on the things that are currently relevant to me. And a big thank you to my boyfriend for sitting down and taking the time to contribute, too. We wrote our responses separately and without discussion as to be unbiased.

How often do you guys go out with friends separately (i.e. maintain your lives outside of each other and stay individuals instead of always being a “we”)?

me: I usually only go out alone when I feel like a girls night or when a friend is in town. I have a few drinking buddies and a few writing buddies which are great too. I would say a couple times a month do I “go out” without him. Otherwise its group gatherings or double dates.

him: I would say about 2-4 times a month.  However, this more or less mirrors our behavior before the relationship–Lo and I are both introverts, i.e. socializing tires us out instead of energizing us.  What works for us might not work for others–some might need more outside social time.

How do you keep the magic alive when you see each other as frequently as you do?

me: He is pretty courteous. Notes and flowers, not farting in my face, being respectful of our shared space, he always looks nice. Lots of little things. My favorite thing is that feeling after you laugh with someone. Goofy inside jokes. That kind of thing. Finding a balance between routine and special dates helps too. I like that he cooks breakfast and I cook dinner. I also like when we say fuck it, dress up, and go out for a nice meal.

him: I’m of the opinion that “magic” isn’t just always there–it’s something you create and work at.

I believe in the past you’ve talked about how important you think it is for people to still masturbate even if you’re with someone. Do you guys still masturbate? If so, how do you find time to do it (do you do it mutually or find time by yourselves)?

me: Occasionally, but not that much. I have no idea how he’ll answer this one. I’m almost always home when he’s home, but we are apart sometimes. If you have to get off, you have to get off.

him: I don’t masturbate that often–I just don’t really have the time or inclination. Lo has a higher sex drive than me and is pretty much game whenever I am unless she is sick or it’s shark week. Even with the latter she takes care of me. I expect she masturbates far more than I do as she is home more often studying and can easily procrasturbate.

How do you guys handle money? Do you have a joint account or still keep everything separate?

me: We keep everything separate and split bills 50/50. At this point there isn’t any need for a joint account and it’s not something we’ve talked about doing. We try to keep a pretty even balance of things but because he makes more than I do I begrudgingly let him pick up a little extra every now and then. We split bills and groceries using the square cash app. A couple times a month we tend to do shorter trips to the store separately (pick up necessary items, things we’re craving, stuff for dinners) and it doesn’t seem to be a problem.

him: It is separate.  We more or less split everything, though I intentionally pay for more stuff given that make much more than she does. I still think she pays for too much but she won’t allow it, which I love.  If I invite her out to dinner (i.e. with my parents) I always try to pay.  I will say that I had a bad experience in the past and that it is, really, really wonderful to deal with money on a rational level with Lo.

Do you cuddle on a nightly basis or was that given up long before you ever realized you could co-habitate?

me: We rarely take cuddle breaks throughout the day. There is plentiful cuddling. We don’t really “sleep cuddle” though, unless you count fighting for the blankets and my legs somehow ending up over his side of the bed as cuddling.

him: Dear reader, I don’t want to read into your question too far, but if cuddling is something that is important to you, you should be able to meet that need in a relationship without twisting anyone’s arm.  Here’s my unsolicited advice–tell your partner how you feel, or gtfo. Love, Jason

Now for my actual answer–
We cuddle all the time, and even if we’re not cuddling usually we are touching somehow if we’re within that distance. If we stopped cuddling I would think something was very wrong.

Hi, I have a question based on a previous relationship I had. We moved in together and after a few weeks, he started irking me to the point where I didn’t want to have sex…I’m not sure if I was overreacting, but the problem was that when I brought up to him that I don’t like him doing x and y, he didn’t think that those things were something he should’ve considered as not ok behaviors in the first place. It was a myriad of things, not closing the door when he went to the bathroom, not spraying the air freshener after he did, kicking food he dropped under the fridge. I just felt disrespected above all I guess. How can I avoid a similar situation in the future? Please tell me if I was overreacting or handled the situation in a wrong manner. Thank you.

me: There are a lot of little things that you notice when you live with someone that they might never notice they do. For me the biggest part of living with someone is that moment you realize I am not the only one that lives here. People have different ways of behaving when they are alone and those behaviors can take a while to change or get used to. I don’t know how you had that conversation with him. He may have been defensive or embarrassed being called out on things that he had been doing his whole life. A good plan is to nicely ask your partner to do things differently and explain why. “Hey I got this stuff for us to spray after we use the bathroom. Can we start using it together?” Try to be lighthearted about it, don’t make it a serious personality flaw that he doesn’t spray in the bathroom. Just gently get the point across that all the tension will go away if he can make a small painless change in his system. Make it clear that you are willing to do the same for him if something comes up. If he says “no” or “whatever babe” then you might be dating someone who isn’t mature enough to deal with cohabitation.

him: I think you did the right thing by telling him your standards of cleanliness and how comfortable you want to be with each other.  He should have said “Sure baby, no problem.”  What the hell skin off his back is it to close the door when he takes a dump? Consider yourself well rid of this cad.

Is it realistic to expect that we’ll have as much sex as we do now if we live together?

me: Yes. I do think when you don’t see each other every day there is the perception that when you do see your partner the desire is more instantaneous. You may need to find new and creative ways to get in the mood if you don’t have those periods of absence. But if you want it, strive for it.

him: Sure! Why not?

How do you combine his stuff and your stuff if you have different styles?

me: I think it can be a transitional time. Try to pick what things you can or can’t live without as time goes by and see what your style is developing in to. If you have the money, you can pick a style together. An easy way to do that is to pick one favorite item (a color, a couch, an era) and choose the rest of the house around that.

him: That depends on a lot of things–which partner has nicer stuff, which partner is moving in with the other, which partner is the better decorator, which partner cares more about their stuff, what makes more sense from a spatial perspective. From there you just compromise.

Who does what around the house? How do you break down chores and shopping?

me: I like the big trips to the store, it’s fun to me. I also like cooking big dinners so I can get all the ingredients I need. He does quite a bit of shopping himself too though, and we almost always go together. We haven’t figured out chores yet. We only just unpacked and theres a lot of organizing left to do. So far the only real thing we have set up is that whoever cooks, the other person does the dishes. I think he’s going to save me from shower cleaning duty.

him: We haven’t been living together long enough to get into the routine, but so far Lo has done the majority of the real housework. I don’t want to diminish her schooling because that is stressful and worthy, but she does have more time here at the apartment (I work 8-10 hour days).  I try really hard to keep up with my end of the chores (she cooks, I clean up) and so forth.  We each do our own laundry and usually go shopping together and split the bill.

How often do you talk about the “next steps” in your relationship now that you’re living together?

me: We don’t really. I’ve told him that I like that he’s real, and talking about big things doesn’t freak him out, or send forth impending doom notifications. That’s about as far as it’s gone.

him: Not at all so far.

What is the weirdest thing your so does around the house that is also endearing?

me: I’m trying to think of something particular that is different from before he lived here. He’s taken up my habit of giving objects personalities. I have to be careful because he might not be talking to me, he might be talking to the pita bread.

him: Pretty much everything Lo does is endearing.

What were your reasons for moving in together?

me: We spent most nights together and I think I personally reached that moment where it was silly to always be packing for several day stays at the other persons place. (Mostly him.) Also I knew he was a keeper. I didn’t have any reservations.

him: I love Lorelei and I knew living with her would be amazing and fun. I love seeing her every day. I was practically living here anyway.

Do you think theres a difference between moving in together and getting married?

me: I think so. We’ve talked about this a little bit I think in the past but for me I keep coming back to the same thing. The tone of getting married is different. When you get married it’s more about melding your family or making a family together than just cohabiting. (You can certainly do this without getting married, as well.) Living together can mean a lot of things but deciding to get married is decidedly “I decided I want to do life with you.”

him: Yes. The difference is that they are different.

I don’t live with my gf yet and am worried if I do that I won’t have time to myself. She isn’t totally unsupportive of this and I’m not sure how you feel about it but I play a LOT of video games. I’m worried if we live together that she is going to make it a big deal and it’s not something I think I’m just going to grow out  o f.

me: If you’re an adult who plays video games and thats something thats important to you, find a girl who also likes video games, or a girl who understands that part of you and the culture itself. Also be aware that when you move in with someone you do change your behaviors a bit. Make sure you have time to do the things you like to do but be aware of how things have changed. Like spending time with her, being present and aware when you’re having a conversation, turning it down or wearing headphones when necessary, or having a separate room for it. Remembering to do what you need to do before you do what you want to do goes for everything, not just gaming. I think moderation is key.

him: If you have fears about having personal time, you should communicate that to your partner before you move in.  Your partner also deserves to know how you plan to spend your time.  You probably will find that you have less time to spend playing video games because you will be spending more time experiencing the world with your SO–and that’s a good and worthy thing.  My warning to you is that generally people who live together don’t carve out a lot of time for solo leisure activities. The whole point is to find lots of things that you can enjoy together.  Then again if she’s cool hanging out reading while you blow up aliens and that works for you guys, more power to ya.

Easy: What is the best part about living with someone you care about?

me: Seeing him at the end of every day, and making all those mundane parts of life better.

him: You get to hang out with them ALL the time!

How would you soothe common fears about living with a significant other?

me: I’d want to know what those fears were. Then I’d want to know if you felt comfortable talking to your s/o about them. Getting it out there is the first step. Sometimes its just right.

him: Sometimes you just gotta take the leap.

That wraps it up! If you have any more questions specific to cohabitation, submit at the top by hitting ask advice and I’ll answer it on my blog. Otherwise, we’re back to your regularly scheduled blogging.

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Question: Asexual?

Hello, I was wondering if I could ask some questions about asexuality. I sort of suspect, after a few hours of googling, that I am asexual. I’m 20, female, and a virgin, and though I’ve found guys attractive, and I’ve kissed before, sex never seemed appealing. I’ve been spending a lot of time with a guy friend of mine, I care a lot about him, and I love touching/hugging/laying in bed with him, but I can’t imagine having sex with him though I find him attractive. We’ve held hands for a long time which felt really intimate and satisfying…which confused me and I felt like a weird prude. When I asked him if he wants a girlfriend/likes any girls (I haven’t expressed to him how I feel and lied and said that he’s like a brother to me which made him pretty upset so I asked him that in a caring friend way not so much be my boyfriend way), he brought up that he “isn’t looking to have sex with anyone” and there was one hot girl he had sex with but he doesn’t want to again though he could…he also mentioned that he guess he’s too picky (which I thought I was too in the past as the reason for me still being a virgin at 20 for no other reason really). So I’m just really confused. I feel inadequate and like he doesn’t want me. Which makes me really upset and causes me to want to stop talking to him altogether because it hurts. Sorry I don’t mean to sound selfish but I’m just trying to make sense of how I feel. I feel like I want to want him but I’m not quite there yet, but I don’t know if I should try to kiss him because I don’t know if he wants that…sorry if this makes no sense. Also sorry for the rambling, I kind of wanted to give a backstory. My main questions are how can I assess if I am asexual? Based on what I said, do you think I am? Your insight and advice would be so, so appreciated. If you also could please advise me on what to do/say/how to act with my friend, I would be really grateful as well. 

It is helpful for me to think of asexuality like any other sexual orientation. Exploration doesn’t necessarily change who you are, but it can help you understand more about yourself. It can be a tricky road for some with lots of bumps in the way. I cannot say whether or not you are asexual anymore than I could tell a woman she was a lesbian. Behaviors are complicated, just like the mind, and they don’t paint a clear picture of whats going on inside.

What I’m trying to say that it’s okay if you don’t have it figured out quite yet. What isn’t okay is feeling pressured to figure it all out right away, or feeling pressured to “fit in” by doing or saying certain things. Do not kiss this guy unless it’s something you really want to do. You can appreciate the intimacy that you have together without wanting to have sex. These things don’t necessarily lead to one another. It could be that your friend is just as happy with what you’re doing as you are.

I do think its important to communicate. If this is becoming a relationship of sorts, its important to talk about how you feel, or your boundaries, particularly if things feel to be progressing physically.

I would recommend getting on boards for asexual communities and asking their direct advice if you feel you need further support. This one looks like a good place to start.

I don’t want to express “you just haven’t found the right person yet” because that’s a silly idea. Perhaps one day someone will come into your life and you will want to explore your sexuality, but perhaps that won’t happen. There are plenty of people out there who express their intimacies in different, non-sexual ways. People are asexual sometimes. That’s perfectly normal and, although it can feel frustrating, or inhibiting, can be empowering if you learn to love yourself just for who you are.

Aside from all that, getting exactly what you want feels good, and doing things you don’t want feels bad. Chase the good.


Do you have a question about sex or love? Submit at the top by hitting ask advice and I’ll answer it on my blog.

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5 Different Non-Monogamous Relationships

I love my girlfriend with everything I have, but she is far away and I find it hard to feel my sexual needs are adequately being met by masturbation over the phone or Skype. How do I approach the idea of having playmates, but keeping our relationship to just the two of us?

This is a great question, thanks for asking! 


Many couples are finding that ethically non-monogamous relationships work, and work well. There are a whole variety of non-monogamous relationships out there. Some you may have heard of, and some may be new to you. While people may interpret these words differently, this is how I interpret them myself.

1. Swinging

Swingers might practice more socially organized non-monogamy. They might attend groups where partners or couples swap. They may attend swingers clubs, where one might have sex on site (or on sight, wink nudge.)

2. Polyamory

Polyamorists might value the intimate and loving parts of their relationships more than just the casual sex aspects. Someone who is poly believes that it is possible to love more than one person at once.


3. Cuckoldry

A cuckold is now often referred to as a man who gets off on the idea of his female partner having sexual contact with someone other than himself. This female partner is sometimes called a “hot wife.”

4. Open Relationship/Marriage

An open relationship or an open marriage has less strict definition in my mind. An open relationship is a relationship where the partners involved have discussed and found ways to include others in their relationship in some way. Sometimes this means one or both partners will have casual sex partners. Sometimes it means there is another relationship within that relationship (such as another girlfriend or boyfriend.)

5. Monogamish

Monogamish is a relatively new term coined by Dan Savage. It describes relationships that are mostly monogamous but not entirely. An example would be a couple who considers themselves monogamous but, as is becoming popular, they may engage in threesomes occasionally.

Ethically non-monogamous

Basically, ethically non-monogamous relationship is a fancy way of saying that you have created a relationship between you and your partner/s that suits all of your needs, but does not necessarily follow a traditional relationship model.

I believe that all relationships would benefit from questioning the traditional relationship model by asking themselves what they want and need. In your case, your long distance relation struggles with physical intimacy needs.

I think it’s important to remember that when you do open your relationship to someone else that you are opening your relationship. You are, in some way or another, involving them in your partnership. Even if you are keeping you relationship separate. For instance, you will have new conversations about trust with your s/o, and safety, STDs, and protection.



You also have to consider the other person or people involved. Where would you find a new partner and would they want the same casual arrangement as you? This can be difficult to find, particularly if you are going to be honest about the fact that you are in a relationship and aren’t looking for anything serious.

Some couples I know go for a don’t ask don’t tell model. While I have never particularly advocated this model, it does work for some.

I would suggest that you ask your partner about this and see what she thinks. Does she too desire playmates? If not, does she understand and support your desire? Depending on how these questions get answered, you may have to start asking other questions. Like how you can continue having your needs met, or if this is the right relationship for you.

I think it can be a good idea if the time is right, the people involved are right, and the spirit of the idea is right. A conversation about how you feel and brainstorming potential solutions with your partner is a good place to start. Good luck, and feel free to submit further questions as you get involved in this process.

Have a question about sex, love, or life? Submit at the top by hitting ask advice and ill answer it on my blog.

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Question: How do you get your shit together?

Do you have any advice on how to get one’s “shit together”? I’m a college student and there’s so much to straighten out and figure out, I don’t know where to start. And the overall life situation I am in gives me anxiety and I feel too overwhelmed to attempt any steps to legitimate change. Also if you could give some advice on how to pick a major I would love to hear your perspective. Thank you for your amazing blog.

There’s no real secret for getting your shit together, some people are better jugglers than others.


If they’re not too good at juggling, sometimes they:

1. Pretend they know what they’re doing

2. Only show people the side of themselves that is with-it giving a false perception that they are completely competent

3. Know how to laugh at themselves and the ridiculousness of their situation

4. Know how to see something beautiful in something ugly.

I don’t know what I’m doing all the time. When things are going my way and everything is just awesome I usually figure that I’ve forgotten about something important.

What’s important to remember is when someone is doing very well, that doesn’t necessarily mean they don’t have problems of their own. If you put a lot of time and attention into one thing, its easy to let something else drop. And even if it does appear that they have it all together, that doesn’t even start to cover the fears and insecurities they might have within their head.

The biggest mistake you could make is believing that anyone has more ability to be awesome than you do.

What would I do?

As usual, make a list. I love lists. I love lists about lists. A good list can turn a shitty day into a shitty day that you can strike out with a sharpie.

A list creates direction and it pulls all the anxiety from your head onto a piece of paper. Put some easy shit at the top. Like, brush your teeth. There, you can strike that off the list. You’ve done something today, good job. Now that you’ve got the ball rolling, write down all the stuff that scares you. Choosing a major. Registering for college. Paying for college. They break those things down into small chunks.

[  ] Choose a major

What do I want to do?

What is important to me in an education?

Will my education help me get a job?

What would I like to do as a job?

What is important to me in working, and a career?

The best question I’ve found is this: what do you actually like to do? Do you like to draw? Make music? Sell things to people? Write books? Teach? Code? Build things? Do you like to help people?

No one ever told me this but it doesn’t take a computer program to tell you what you’d be good at. You’re usually the best at the things that you like to do. School can help you find ways to make that skill practical. It can fill in the fundamentals. It can help you expand your knowledge and skills.

There was no option for “write a blog about sex” when I was in High School, clicking multiple choice bubbles trying to decide what I wanted to do with the rest of my life. And while there was an “author” option, the hell if I knew what being an author meant when I was 16.

You have to get out there and try things and see what fits, what feels good. Would you buy a pair of pants off the internet? (I mean, I wouldn’t.)

So try some things on.

I would advise getting accepted into a community college and signing up for a term of electives. You’ll need elective credits anyways, so why not?

Lastly, I would highly recommend seeking out mentors. Do this when you have some general idea of what you want to do. You can even just pick someone who has a cool job and talk to them. This is the one thing I have failed miserably at because I have confused asking for help (something I stubbornly dislike) and asking for direction, advice, and networking (something you should do to get anywhere in life.) Never be the smartest person in the room. Never be bored. Always be asking questions. Take an interest in all people and things.

Okay, if that’s not enough to send your anxiety up a few levels, I don’t know what is. List making, it helps. Draw lines and circles and try to figure out what small steps you can take right now to make bigger steps later down the line. Best of luck.

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Question: A Good Reason to Fake Orgasm?

Question: Do you know of any good reason why a woman would fake an orgasm? 

Answer: I am usually pretty adamant against faking orgasms. However, there is one reason a woman might fake an orgasm that I can understand as somewhat logical.

Many women have a difficult time orgasming during sex. For some, this can lead to orgasm-faking.

Why would someone fake an orgasm?

1. They feel that their male partners judge their own performance (and your satisfaction) based on your orgasm.

2. They believe that the point of the sexual experience is to orgasm and feel let down by that sexual experience if they are unable to achieve an orgasm.

3. They don’t know where to find a clear end to sexual intercourse without an orgasm.

4. They feel frustrated that they are not in control of their body and that if they were more “sexually aware” orgasm would be easy.

5. They feel that they or their partner is not pleasing them well enough or that they are an unskilled partner.

There are a lot of pressures that might go through a woman’s head when she is having sex. 

Does my partner find me attractive? Am I jiggling in all these weird places? Am I doing this right? Am I pleasing my partner? Why doesn’t this feel like I thought it would/should?

For some, these worries are tied to other insecurities. For others, these worries are picked up second hand through media influences or whatever kind of half-assed sexual education they got. (A lot of sexual education emphases male pleasure, not female pleasure.)

So, here’s the reason women might do it that makes sense to me.

Women might fake orgasms to reduce the pressure to orgasm, allowing them to orgasm more easily. 


If you are having sex and your partner believes that the hard part is over (I made her orgasm, sweet!) she may cross a lot of these fears off her list. Performance anxiety, and satisfying her partners desire to satisfy her, at the top of that list.

Without those concerns she will be able to more easily let go, and get in the moment, which will make an actual orgasm more likely.

Obviously the ideal situation would be that the two partners would communicate what feels good and what doesn’t feel good and when to stop and go and the sex would improve through that communication. For some women, this short-term solution might help them understand what letting go feels like. It may also be beneficial in casual relationships where you know you may not be building a long-term sexual relationship with that particular partner.

To wind back up where I started, please try to avoid orgasm faking. Consider that you and your partner are reinforcing poor sexual habits if you tell one another “that works for me” when that doesn’t work for you. It may be more difficult to slowly work towards that release, but I believe that faking orgasms can very easily set you up for continuous orgasm faking, which would make it difficult to then be honest with your partner.

If you want to reduce the pressure of orgasming, or if you’re simply finding it difficult to become aroused, there are other, better solutions out there for you.

Do you have a question about sex or sexuality? Do you need relationship advice? Submit to the top by hitting ask advice and I’ll answer it on my blog.

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Question: No Hormones. Should he pull out?

Question: My partner and I have used condoms for the entirely of our sexual relationship, but I am not on hormonal BC and I don’t think it’s a good option for me right now. It would be fun and enjoyable to go without condoms sometimes, even if it was only for the beginning of that encounter. I’ve always been paranoid about doing anything without a condom – ‘but what about precum?’ – but saw recently somewhere that sperm isn’t actually in precum, it can only be carried by precum if it already exists in the urethra from a past ejaculation. To keep this from being the case, the dude should pee before sex to get all those little squiggles right out of there! Is this a reliable thing to believe? If so, then if he makes sure he’s ‘flushed’ any older spermies before we have sex is it safe to start having sex without a condom and then pull out and put one on -well- before he gets close? I’m not talking last minute thing here, I’m talking things are getting more intense so to avoid a close call we pause, wrap it, and carry on. If this is a dumb idea, whatever, we’ve been happy having sex with condoms 100% of the time for like 3 years now so it’s no biggie to continue on until we figure something else out, but it’d be cool if this was a reasonably effective compromise I guess.

Answer: There aren’t really any definitive studies on whether or not there absolutely is or isn’t sperm in precum. Some studies say one, other studies say the other. What it usually boils down to, for me, is this. If you don’t want to get pregnant, and you’re not on birth control, use a condom. Always, one hundred percent of the time. To me that experience would not be justifiable if the result was potentially risking an unwanted pregnancy.

But, that experience may be worth the risk to you. If it is, I would recommend agreeing that you are only going to see what it’s like, and then stop. I would also recommend that you choose a less fertile day in your cycle.

Be wary that it is very very very easy to push your own personal boundaries once you’re in that position. This feels great, lets just go a little longer, just a little longer. It’s easy to push that from “lets just try it at the start” to “lets just go until you feel like you’re going to cum” to “well lets just try this once it won’t hurt.” Not to mention that even if your partner feels like they have a good hold of their muscles and their ejaculation-intuition, you never know when one thrust might send him unexpectedly over the edge. It’s necessary to consider all outcomes, you know?


I would also recommend that you talk to a doctor if possible about low/no hormone options for you aside from condoms. (Options here.) You know your body best so if hormonal options aren’t a good idea for you right now, I really would recommend that you keep using the condoms. A spoilsport, surely. But as said above, there may not be any harm in pushing the boundary once or twice, with knowledge that it is risky behavior, and quite easy to accelerate.

On that note, congratulations on your three years of happy fucking, and I hope they continue!

Do you have a question about sex or love? Submit by hitting ask advice at the top and I’ll answer it on my blog.

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Question: My Boyfriend Won’t Clean, What Now?


Question: Concerning cohabitation – dividing up housework. My guy and I share most of the cooking and laundry duties but when it comes to cleaning, the lions share falls to me (I’m female). His responsibilities are taking out the trash and vacuuming. Our apartment is about 1000 sq ft so I don’t think this is a major task yet he drags his feet. I’ve offered to trade cleaning toilets and using with him but he continually insists that he wants to vacuum. I don’t want him to WANT to vacuum, no one wants to clean, but he’s getting on my last nerve when time to clean comes around and he brings up hiring a maid! It takes less than 10 minutes but I feel that I get my jobs done and he is still sitting around, playing Halo or reading a book. Side note – I work full time and he is a student currently on summer break with no internship/job/responsibilities outside the home. I don’t want to nag him or yell or fight. I’ve tired asking for a deadline as in “by the time I come home from work on Wednesday, that’s three days from now, the house will be vacuumed” but he still puts it off to the last moment. It really irritates me and I don’t want to fight every week about a simple task.


I’m sorry to hear that you’re having a rough time in your relationship. There are all kinds of things that can send you up the wall when you’re living with someone. Sometimes those small grains of irritation can build up into larger, more substantial irritants. I would suggest that this is likely one of those cases. Is the issue really about vacuuming, or is there something deeper going on that is making this such an issue for the both of you?

We all have shit we don’t like to do. It’s the stuff we put off until the very last minute. I’m pretty bad at this. My to do list gets crossed off in order of fun, not necessity. I’m pretty cognizant of this and make an effort to do things that I need to do. In your boyfriends case, that thing would be vacuuming the fucking carpet. He doesn’t want to do it so he does what he wants to do, perhaps with good intention. I’ll do it eventually, that’s what counts, why are you getting so mad? 

Unfortunately for him, it’s not just on his to do list, it’s on yours too.

That’s a shared space and that means that this particular task needs to take higher precedence. Not only that, but he needs to realize that this particular matter is causing you distress. Perhaps because you know that you cannot rely on him to do something so small and simple and so fundamental to the mental well-being of you and your relationship.

The problem is that you now expect this negative experience.

Truly, that’s one real big problem. You don’t believe that he’ll do it so much that you’ve set deadlines. You steam about it while you’re not there. You just wait for him to disappoint you. That’s not fair to him just as it is not fair to you.

Is your partner depressed? Sometimes when we are depressed we can show similar behaviors as your boyfriend is showing. Sitting around all day, unable to do the things we need to do, frustration when we are called out about it. Is he having trouble using all this free time he has in ways that are productive? That in itself could be cause for worry.

It’s one thing to have lots of free time and find ways to enjoy it, it’s another to lose complete track of time and realize you’ve really dropped the ball.


It could also be a problem if you have a different maturity level. Are you at a point in your life where you just want a clean home to come home to so you can focus on getting things done, and he’s… at a point where he wants to play video games? That can cause friction in itself.

It’s also valid to point out that perhaps you just have different ideas about cleaning. To you cleaning might be a basic necessity, something you do because you need to do it. He may not have grown up cleaning, he might not know how to clean, he might not recognize when things are dirty. To him lets hire a maid might be a clean solution to the dirty question.

Let him know that hiring a maid is not a reasonable response, but try to do it in a way that recognizes that to him, it might have been reasonable.

When you talk to him again try to make sure that this is the last conversation you ever have about vacuuming. No one wants to talk about vacuuming that much, not even you, I bet. Find a place of mutual understanding and respect and work towards discovering new and more exciting disagreements to have with one another.

Before you do any of this, think about whether or not the conversation really has to do about vacuuming. If this one simple thing could be solved, would you be happy? Or would you still have that core feeling that you couldn’t trust your partner to do these things? Would you still feel like you were behind the scenes orchestrating his basic adult functions? Would you still feel… lopsided? If the vacuuming isn’t the issue, find out what is. I offered a few suggestions (re: different maturity levels, depression, inability to organize time, different ideas about cleanliness) above. Best of luck.


Do you have a question concerning cohabitation? Do you have a question about sex, sexuality, gender, love? Submit now by hitting ask advice at the top and I’ll answer it on my blog. 

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