How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
I’m in my late 30s. I’m still close with my childhood best friend I met when I was 10. We live in different states. Leading up to her divorce last year, we talked on the phone several days each week for about an hour each time. I was basically her sounding board and cheerleader.
I thought her crisis would end after she and her kids settled into a post-divorce home and life. It didn’t. She still called regularly in distress, often over whatever guy she was dating, even if she’d only known him for a few weeks. I started to ease off the phone calls, but we still talked weekly and texted multiple times a day. Then, in her second serious relationship since the divorce, she cheated on her boyfriend after deciding to leave him—and lied to him to cover it up. She’d done something similar before her divorce, too. I talked to her about it, commenting that it seemed like she used him because she was afraid to be alone. She said she felt no guilt since she broke up with him shortly after cheating. She also reminded me that words hurt, and she needs to not feel judged with all she’s gone through. I don’t think holding a close friend accountable is “judging” and tried to explain. She said that I should of course speak up if I see her doing something “bad,” but she didn’t need my feedback on this.
After a few weeks of only having short, superficial conversations, we talked. Not only is she back together with the guy she cheated on (and had complained about the entire duration of their short relationship), but they’re “in love,” and she’s talking as if she’s going to be with him for life. She never came clean about the cheating and lying. She said it’d be “selfish” to tell him, since it’d hurt his feelings and the only purpose would be to clear her conscience.
How do I proceed? I’ve tried to be her friend as normal, but men are always central to any conversation she wants to have, and it definitely bothers me to hear about him. Every time she tells me about some nice thing he does, I catch myself thinking, “I bet he wouldn’t be doing that if he knew you cheated!” Is this a sign that we just have different values and priorities? She’s also talked about wanting to come visit me and bring him. I didn’t say so, but I’m not interested in putting myself in that situation while I feel this way. I was her maid of honor in her first wedding, and in the past, she’s made comments saying I’ll have to do the job twice. I don’t think I’d want to stand in her second wedding if it’s to this guy who she cheated on and lied to so early on without ever coming clean. I might be jumping the gun even thinking about it, but she seems keen to rush things. Am I ruining a 25-plus year friendship because I’m being too judgmental?
—My Best Friend’s Wedding
Nope. You are being totally reasonable here.
Let’s talk about friendship, even though that’s not exactly the scope of this column. Friends—real friends—do hold each other accountable. Fake friends are the ones who’ll tell us we’re “doing great, sweetie,” and our behavior is perfect, and basically never do the work of reminding us to inhabit the better aspects of ourselves or give us pushback when we’re being unreasonable. In my estimation, you’re trying your best to be a good friend.
I haven’t experienced divorce myself, but I’ve seen a few. Divorces can send people into a tailspin of self-centeredness and frantic attempts to self-soothe. The validation and security a person had became accustomed to can leave a gaping void when a partnership dissolves. Your friend is hurting, and acting like a jerk to this guy—and to you. My gut says she is using this guy. And she’s definitely using you for emotional support. This is a genuine question: How much support has your friend given you lately?
If I were in your place, I’d send her a letter or an email. I’d explain that I do not support her behavior or treatment of her boyfriend, and express a new boundary—no dating talk. No more sympathetic ears for her sexual and romantic woes. And definitely no hosting her with the guy she’s taking for a ride. If your friend comes to her senses, that’s awesome—you can start rebuilding your friendship. If she doubles down on her insistence that your actions are judgmental, you might want to take some time off from each other. A break doesn’t have to be the end of the friendship, but it might take some of the pressure off of you and help her realize how far out of bounds she’s gotten.
Dear How to Do It,
While talking about a trip to Nevada with my girlfriend, I jokingly asked if we could make a stop at a brothel. She said that it was fine, and seemed OK when I asked again seriously, as long as I did it solo. I plan on talking to my girlfriend more about it to make sure we’re on the same page. But I can’t really find much information about going about the whole business, with or without her. What should I expect when visiting a brothel, and how would I even act? I’ve tried looking for answers online, but I can’t find much information.
Dear Brothel Questions,
It is a good idea to check in with your girlfriend again about this, but to answer your actual question, I reached out directly to the source: pornographer and Nevada brothel worker Kimberly Kane. She had a lot of useful stuff to say. “Honestly, you’re not alone,” she wrote in response to your question. “There isn’t a ton of information about brothel etiquette online.”
Here is her advice, edited slightly:
You say you’re taking a trip to Nevada—are you driving or flying? Keep in mind that brothels are in rural or unincorporated areas because of the brothel zoning laws. You’ll need to drive to the brothel or ask the brothel if they have a car service. If possible, drive yourself. Some brothels offer clients complimentary pickup and drop-off but will tack on a high percentage to the total amount of your visit, making it more expensive. I work at the Bunny Ranch, where rides are 100 percent free of charge (but ALWAYS tip the driver).
When planning a trip to a brothel, it’s best to start your research on the brothel’s website. There is always a robust FAQ page that can answer a lot of your questions about safety and legality. You can also browse the courtesans’ profiles to see which lady would be a good match for you. All brothels are open 24/7, and there’s always someone available to answer questions and take bookings.
Pro tip: When emailing a courtesan, be courteous and professional. Give your name, available dates and times, a brief (nonvulgar) description of the party you’d like to have, and your ballpark budget. I always say, pretend you’re writing your chiropractor instead of a sexy lady. If you send an unprofessional email, you will most likely not get a good response or any response at all.
Even though courtesans are licensed and legal in parts of Nevada, they can’t solicit sex online. Every courtesan has her own rates, and if you’re nice, prices are negotiable in-house. Keep in mind that whatever your budget is, the house takes half, so be conscious of that when budgeting your trip.
Kane wrote that “a brothel is like Disneyland for your genitals, and that level of service should be highly valued.” She considered the lowest tier of services as “south of four figures,” and if that’s your budget, she said, “I suggest being genuinely kind to the ladies. Nice guys finish first in a brothel.” The options increase in price from there: In the mid–four digits, you might get to plan “a bespoke experience with the special lady of your choice.”
It doesn’t sound like your girlfriend has any interest in joining you, but if that changes, Kane also wrote, “Honestly, if you and your partner want to experience a three-way without the headache of navigating it in your community, I highly suggest seeing a courtesan. The most important thing for couples to know when visiting a brothel is to BE ON THE SAME PAGE WITH YOUR PARTNER. If one of you doesn’t want to be there, it shows, and it’s going to be a long, awkward ride back into town.”
Dear How to Do It,
I’ve had a crush on a work colleague for a while. Although we work for the same company, we’re in different departments and hardly see each other in person. Last year, he started sending me flirty messages on social media, which quickly turned into very hot (and regular) sexting. He is in an open relationship, and his partner is aware that this has been going on. We’ve even had a three-way sext session. The problem is I’d like for things to get more physical. He says he wants to as well but is hesitant because he’s never been sexually involved with someone from work before. He doesn’t think that working together is a complete deal-breaker that stops things from possibly becoming more physical in the future but needs time to get his head around it. In the meantime, he still wants to keep up with the sexting, but this just isn’t enough for me anymore, and I’m desperate for things to become more physical. To be clear, I’m not interested in having anything but a casual hookup with him, and I’ve been very upfront about that. What should I do?
—Work and Play
Dear Work and Play,
What happens if you’re offered a promotion, but it’d mean moving to this guy’s department? Are you going to tell your boss that it wouldn’t be appropriate because of your sexual relationship and turn down the opportunity? Or will the two of you attempt to cease sexting and—potentially—sexing? In case it isn’t clear, I think it’s a bad idea to continue this workplace liaison. Yeah, sure, people do it all the time. But if “everyone does it” was enough to assuage your mind, you wouldn’t be writing in, would you?
There are other hot, crush-worthy humans in the world. Go find one and get going on your groin grind.
Dear How to Do It,
I am a freshman (woman) in college and I want to have sex. Really badly.
However, I have zero experience whatsoever. I’m not worried about seeming silly or doing something wrong—I’ve gathered that that’s pretty much inevitable—but what I am worried about is my “firsts.” I’m a bit of a romantic, and in high school, I had always treasured the hope that I would meet someone I liked who liked me back, they would give me a first kiss I would look back on fondly, and eventually I would have a respectful and enjoyable first time with them. Eventually, I thought, we would part ways, and I would head off to college ready to have pleasurable sexual encounters with whoever I chose, without having to worry about having a tarnished memory of my firsts. Obviously, that dream did not materialize into a reality. But still, I really want my first times to be with someone I know is a good person, who I like, and who I trust.
But I am also incredibly horny. I’m not sure if it’s a human connection thing, or just a hormone thing, but I want to have had sex yesterday. So I’m torn between my desire to treasure my special first moments, which has always been important to me, and my desire to get pounded, which is becoming increasingly stronger by the day. Sorry if that’s too much. And now I’m at college, and it would be so easy to do that! In theory!
Honestly, I’m really stuck on the kiss thing. I feel like I would be OK losing my virginity to an attractive, respectful, decent person that I didn’t have a close bond with, but I really don’t want to compromise on the kiss thing. I want my first kiss to be someone who I care about and am attracted to, and who cares about me and is attracted to me. I don’t think it’s unreasonable to want what I want, but my desires are now so opposite each other that I feel that I can’t have one without the other. Would it be bad to just sacrifice my first kiss so I can finally start having sex like I’ve been dreaming of doing? Should I sex now, kiss later? Where do I go from here? Is there any way I can have my cake and eat it too? Before you suggest masturbation, it’s just not cutting it anymore. Please help me.
Dear Losing It,
Don’t make excuses or apologies for your sexual desire. It isn’t too much. Well, as long as you’re still able to get the rest of your life handled, it isn’t too much.
You’ve put a whole lot of pressure on yourself here. I get it—I remember puberty, when it seemed like every other young woman had fantasies of rose-petal-strewn beds, candles, and simultaneous orgasms the very first time. On prom night, no less. Romance can be heady, and we’re all exposed to so many unrealistic depictions of it that we can encounter difficulty being happy with, well, mediocre.
What if you find someone where there’s mutual care and attraction, and it turns out that their idea of a great kiss is filling your mouth with their flaccid tongue and wiggling it, just a little? Or they’re one of those people who try to suck your lip off like it’s some kind of flesh oyster? Or they taste bad to you? Is that going to tarnish your memory? I worry that you’ve built this up so much that you’re setting yourself up for disappointment.
I’m 33. I haven’t thought about my first kiss in maybe 15 years. I might not ever have thought of it again if it weren’t for your question. My first kiss was truly, deeply, meh. It was with a childhood friend who I’d started dating. Neither of us knew what we were doing. He pushed his tongue into my mouth and left it limply laying on top of my own. It was kind of gross. I didn’t kiss again for somewhere between six months and a year. Kissing just didn’t seem that appealing. If I were to have a first kiss again, I would pick someone more experienced. But that’s me. And I’m not really romantic about rutting.
You get to have boundaries, and they can be literally whatever you want. There’s a world where you can say to people “I want you to go down on me, pound me, make love to me, but I don’t want to be kissed.” Some people might think that’s weird, or have questions about why those are your limits, but you might be able to find someone who is happy to bone you without mouth-to-mouth contact. Who knows—the sex might help you find the mutual care and attraction that you want to experience the first time you purse up your pecker. Best of luck.
More How to Do It
I’m a late-20s woman. I recently went on few dates with a “nice,” cute guy, and we hit it off enough that I invited him up after the third date. When we started having sex, all was fine until, when we were marching to the finish, he started saying pretty horrible things to me. First it was “whore,” then “you like that, you stupid slut?” and then one other thing I’m not even going to type. I was extremely turned off and wish I had said so immediately—if he had been paying attention to my face at all, he would have noticed. It was weird after, and he left. He is now texting me as if he’s confused why I was distant. Others have told me this is more of a tic than anything for a lot of guys. Like, really?