Fantasies, Photography, and “My Best Friend’s Boyfriend”

by A Lady

I hate my best friend’s boyfriend. They have been dating on and off for about a year, the “offs” came about because he cheated on her, three times with three different girls. Each time, I did the required “you deserve better, you are too good for him” dance, yet for god knows what reason she recently got back together with him, and of course it is “different this time.” Because I have nothing nice to say to her about the situation, I choose to say nothing, and our relationship is suffering. It probably doesn’t help that she knows I hate him, having said many mean things about him the last three times they broke up. I can’t be around him, I definitely can’t be around them together, and as of late I am so frustrated it is hard to be around her. What do I do, how do I get over this and get my best friend back?

Oh, this ancient problem. There are legitimately millions of cave paintings of women going like “him? Are you sure? Are you sure you’re sure?” to their best friends. I feel so at peace and connected to our albino alligator doppleganger cave ancestors when I think about it.

Here’s what I want to know: Is part of the problem that she KEEPS COMING TO YOU with the same drama? Because that’s not a problem with your best friend dating a juicebox, that’s a problem with your best friend acting boring. My basic breakdown is: Come to me with a problem one time, you get hugs. Come to me a second time with a totally identical problem, you get strategy. Come a third time, and you are in Time Out. I like to convey Time Out by responding to statements of the problem with total non sequiturs, e.g.:”That girl from his job was texting him again.” “That’s cool. Why don’t you see a lot of blimps anymore? I miss blimps. OMG, girl, do you think we can take a blimp ride somehow?” If she is trying to fix her problems but runs into new problems doing it, you gotta three-step those from the beginning, they don’t count as the same problem just because they’re part of the same life-zone.

But if she’s not over-complaining . . . could it be that she’s just a grown lady making decisions you might not make? She has know this fool’s not changing absent a Phineas Gage style headwound; maybe she doesn’t really mind the cheating all that much. If this is the case, you’re not gonna get your best friend “back,” you just gotta bite your tongue and make your own grown-ass lady choices about what you can tolerate and how much of a relationship you guys can have without discussing hers. Just kind of always hum Free To Be You and Me, and remind yourself of all the awesome non-boy-stuff you guys have to talk about, like, I dunno, I actually only ever talk about boys, but everyone seems to play tennis, so probably tennis.

But! That was trick advice! No one was ever a confident grownup making life-decisions like a boss! The fact that she keeps breaking up and getting back with him indicates she does on some level really mind the cheating, and and has some sort of confidence ish/fear of being alone. Haha what?! That’s CRAZY, who ever heard of that?! As her best friend, it falls to you to help her get in touch with her interior mutant alligator doppleganger. Makeover of the soul! Idle compliments are fine, but really, like, teach her how to make or do a THING! so she can see herself learning and changing. Crafts and baking and sports (racquetball! who wants to give me racquetball lessons?!) are so good for this purpose. Take her shopping for super-slutty clothes. Introduce her to guys who don’t suck, then tell her they thought she was great. (It’s OK if they didn’t say that, just assume they thought it.) She’ll be broken up with this juicebox and crying to you about how she can’t meet anyone in no time.

I am one of those ladies who doesn’t think she has ever had an orgasm. Now the thing is, I have been sexually active a long time, have had a great number of sexual partners (somewhere over 70 I think?) of both genders and masturbate frequently to some satisfaction. I really like being naked with other people doing sexy things, so it is not a problem with arousal. I am aroused a lot, it just doesn’t ever go anywhere but frustration. I am in two minds as to whether I have actually had an orgasm or not. When I masturbate there is always a point about two to five minutes in where I am done. There is no big climax, I just feel like “Oh, I am done with this.” I have tried to keep at it, but it mostly just makes me sore and uncomfortable. From what I understand it seems to be that I am instantly turned off by anything going into my vagina. It just dries up as soon as you stick something in there. I figured this out when I was like eight and masturbating and poked a finger in there to see what’s what and the whole feeling just went out like a candle dropped in a bucket.

I have tried over and over again to “fix” how I masturbate. I have a vibrator that I have used in conjunction with my usual methods, to no avail, and now it just sits in my drawer collecting dust. I understand that there are loads of women who feel eh about P in V sex, but that always seems to be a “It’s not as good as X” kind of situation as opposed to actively turning them off. I am pretty sure I am doing masturbation wrong, somehow. I generally stimulate about an inch or so above my clitoris because touching my clitoris directly when I am aroused is often just kind of painful. I have no problem getting good and sopping wet from this, but again, it just culminates in a sort of petering off of horniness. The closest I have ever gotten to recreating my pleasant masturbatory experiences have been from anal sex. What does that mean!? Is my clitoris tilted at a weird angle so that you can’t use any of the generally established routes to clitoral stimulation?

So I guess what I am asking is firstly how do you know if you’ve had an orgasm or not? Everyone I’ve ever spoken to always says “You just know!” but that doesn’t really help me because I don’t know! If it is that feeling of being done masturbating, then it has really been oversold to me. It doesn’t go anything like other people describe. It is certainly not “climactic.”

And secondly is my vagina weird? I’d ask a doctor but I have no idea how to broach the subject without sounding like one of those crazies who is irrationally afraid of their vag. Because I quite like my vagina, I just want to know if it’s in working order. None of the doctors I have seen have ever said anything of their own volition.

Also I guess is there a way to fix it? I have done a bit of Googling, and medication and sex therapy sounds a bit grim to me. Also I hate the idea of “female sexual dysfunction” because those words feel so damning. This whole problem makes me feel shitty and ashamed, like I am fundamentally a failure at sex.

Please help! Because of my storied sexual past my friends just laugh at me when I try to talk to them about this and I am sort of grasping at straws now.

Fuck if I ever know what to do with these serious science questions about vaginas. OK. Well. Dr. A Lady says that if those are the orgasms you’re having you’re not having the same orgasms as her. Hers are sort of like uuuuuuuup a rolllllerrrcooooooaster and then DOWNRREALLYFASTAHHHH! except no nausea and no teenagers (anymore). Sometimes the hills are little and sometimes they’re big, but they’re hills. Sounds like you are just kind of plateauing then like, wandering off in the air, like Templeton does with the popcorn in the middle here. Is that an accurate visual representation of your orgasm? FWIW, I kind of have to scrunch my whole body up to have one, not just the like, nearby muscles, and I don’t typically come from P-in-V (because it’s pretty hard to scrunch your whole body up during that). Oh also I was on Wellbutrin for a bit and it gave me siiiick orgasms.

Oh also are you using the Magic Wand or something else, because seriously, the Magic Wand. If you CAN have a down-the-rollercoaster orgasm, that’s the. . . carnie who will belt you in?

But anyway, no, I don’t think it’s weird. Jesus fuck, you guys, have you SEEN humans? They are all over the place! I mean, think about the people you’ve been with and the intensity and variety of their orgasms. I know dudes aren’t all shooting ceiling-staining jets of cum each time. I mean, they always have with me, but my friends are like, stop lying. It seems to bug you enough that one visit to some kind of person who does whatever doctory/therapist thing can’t hurt, but you know, keep in mind, as you’re there in that horrible backless gown, that you’re doing fine, you’re there to ask questions and explore options, not because you are fucked up. Just bring the Templeton video and show them that, they’ll totally understand.

I’m a straight guy who considers himself both open-minded and well-mannered. I’ll admit that I’m baffled by the numbingly regular occurrences of my fellow males sending pictures of their dicks to women, often ones they don’t even know. Sports stars, congressmen, Hollywood types, etc.

I’m far from prudish and I’m not considering joining the trend, but I have to wonder: Has this ever worked? It seems like the creepiest thing imaginable. I mean, I’ve never met a woman who was turned on by a flasher. Is this not the same? Have any of you ever slept with a guy who started things off by texting a pic of of his johnson?

Who “started things off by texting a pic of his johnson?” Dude, no. No lady has ever slept with anyone who STARTED THINGS OFF that way, that’s at least third-text material. That said, if Anthony Wiener had had the sense to hit me up, there might have been a first time (my Lawn Guyland heritage means I’m honor-bound to bang literally anyone with that accent).

OK, so, I have problems (or do I???) with sexual fantasies. Everything I read, people are all, “Whatever you fantasize about is OK! Healthy party of sex! Blah blah blah!” Except in all these things, they don’t address my issue, because what they seem to be saying is, “Whatever kind of fantasies you have where you are doing things you think are sexual is OK!” and I don’t have those. I never have fantasies about me. I just never have. It didn’t occur to me that this was how people usually fantasize until I was adult enough that my friends started talking about their sex lives more explicitly. My fantasies are about other people getting it on. Usually it’s some rehash of a porn I saw, or some sexy scene in a movie, but I’m never in there — it’s just the porny people. I don’t know if other people do this. It doesn’t seem like they do, and that makes me feel weird. Everybody seems to have this huge, wide, diverse range of sexual fantasies, but the assumed caveat is always: and they’re about you. And mine aren’t. So, all the reassuring sex advice I’ve ever heard is about people who aren’t like me, which is terrifically un-reassuring.

I also need sexual fantasies to get off, and I need to have eyes-shut, concentratin’ time to do it. Not to say I can’t enjoy things otherwise, but for the orgasm part, I’ve got to retreat to my porny people place. I know everybody’s different, and some people need such and such a kind of stimulation, so maybe this is not so weird, but when it comes with the “also, I’m not in my sexual fantasies” part, it makes me feel like my whole package is weird. I also don’t like that I have to retreat from what’s actually happening — the actual porny sex that’s being had — to imagine other porny people doing the same porny things before I can get off. It makes me feel disconnected from my lover (or does it??? maybe I just feel that way because I feel all weird about how maybe I’m doin’ it wrong and I should worry more). Other people seem to be able to, like, imagine what them and their lover are doing except, I don’t know, on the beach, and boom, that does it. I don’t know why I have to think of completely fake people instead.

It also makes talking about sexual fantasies weird! I gather that’s something people are supposed to do to spice up their sex life? Talk about the hot fantasy about getting it on at the theater while in drag or something, and then pretend they’re doing that? I can’t act out my fantasies. My fantasies are porn people porning. Sometimes they roll over and porn on the left side, sometimes the right. And we’re kind of already doing that, so the only thing to add to the experience would be “also you’re not here and neither am I, we are porn people.” Because, you know, since I don’t fantasize about myself anywhere, I’m not fantasizing about the people I would like to do, either. I mentioned that to my current boyfriend once, and he was a little disappointed that I never fantasized about him. But he is a nice guy and told me he didn’t want me to worry about it, because he realized it wasn’t about him, and he doesn’t bring it up because he doesn’t want to give me A Massive Complex about it, which is nice. But it does mean we don’t talk about it, which also goes into my shameful pile of “AND MAYBE THAT’S WEIRD, TOO.”

It does make me feel like I’m missing something other people are having fun with. Like, is it especially exciting to somebody to sexually fantasize about somebody they like, then actually get to sex them? Are people having staring-straight-in-your-eyes orgasms without having to think about stuff? How do you spice up your sex life by revealing your fantasies if your fantasies aren’t really interesting and don’t involve either of you?

God, you people worry so much about what is in your fucking BRAINS. If it’s in your brains, everything is normal. When you do stuff outside your brains, like 85% of shit is STILL normal. Don’t let anybody tell you what to do in your brains!

But just so you know how normal this is, um, I hear ya? If I’m fantasizing elaborately, I can’t concentrate on sex. Fuck these multitaskers and their hot wax buxom peasant whatvever. Also problem: Whenever I tried to fantasize about like, “scenarios,” I got super bogged down in details. Like, “are you a real pirate, or a privateer? Are you going around ravishing just anyone, or did you think I was pretty? I dunno, I think you might like my friend better, since everyone ALWAYS DOES. How did I get this house, anyway? Where’s your boat? Are we gonna go out again, or is this like, whatever, it’s cool?”

Also in re the need to Hash This Out with your boyfriend, look, honesty and communication are TOOLS, not ends. Also a tool: knowing when to shut the eff up because you are dealing with someone who is doing a weird passive-agressive thing. Did he seriously say he won’t bring it up again because he doesn’t want to Give You A Complex? Fuuuck that. That’s not nice, that’s “look how nice I am for not acting like you’re crazy, crazy.” Be like, so I started fantasizing about you! And in my fantasy you were not such a fucking princess and could actually deal with not telling me what things to put IN MY MIND.

I feel kind of maladjusted for asking this question, but how exactly does one become a wingwoman? I have a few single friends, both dudes and ladies, that are all total catches (because come on, why would I hang out with sucky people?), but they suffer from poor self image/social anxiety/have had few and far between/mostly shitty/nonexistent dating experiences. I am in a fantastic relationship of almost five years, and it makes me sad that these great people don’t get to have that OMGTRUELOVE that I’m so lucky to have, so I really want to help facilitate that with my friends. But I just have no idea how to do that, especially when these friends can be so down on themselves about it, let alone have the balls to shamelessly flirt with a stranger alone at a bar (which is how I landed my boyfriend). Please, A Lady, walk me through this, keeping in mind there are peoples of differing genders and sexualities I would be potentially wingwomaning. Also, is this even my place? Should I even be interfering in these party-of-one love lives? I just want everyone I care about to be deeply in love with someone who worships them and nobody is lonely forever and ever and ever.

I wouldn’t worry about your friends because they are all probably fucking your amazing boyfriend.

No, OK, OK, sorry, uncalled for, bad A Lady. Look, girl, glad you got it all figured out. But this is reading a little bit like “how do I help my sorry-ass friends be almost as awesome as I am?” Do they really want your help? Look. General confidence-building among friends is a great thing, but unless a friend is coming at you being like THE GENITALS OF OTHERS PUT ME ON THEM, you gotta hold back and assume they’re the best (if still imperfect) judges of their own needs, and like, maybe even don’t want to live your exact life or even want to be partnered?

OK, but some friend, let’s say, is like “help me. Help me be on some private parts/married, ASAP.” The secret mystery is you get them drunk, and they when they think someone is cute, you go up and be like, “oh my friend and I were just admiring your tattoos/shirt/swag.” Then just run your mouth with facts about your friend like “she’s a bank teller! She’s got the best shoes!” Then go to the bathroom. If they’re not hitting it off when you get back, or if target seems more interested in you, WRAP IT UP and move on.

Also the wingwoman is different from the setup, which is where you just make people be in the same room a bunch until eventually they make out.

Previously: Skipped Weddings, the Sex Talk, and Attracting the Attractive.

A Lady is one of several rotating ladies who know everything. Do you have any questions for A Lady?

Photo via Flickr