The trick is to talk to her as if she is a human being. Do not talk about your penis.
Speak to her as if she exists in the real world because this is, in fact, all happening in the real world. The internet is not magic, and you are no wizard. You are no one other than yourself (and honestly, yourself needs to be doing a better job). Treat her like a human being the first time.
If there’s one thing I hear way too much on the internet—aside from “nice tits” and “I bet you’re great at sucking dick”—It’s the standard apology followed by, “I’m actually a really [insert unsubstantiated, unlikely, positive attribute: nice, smart, great, funny] guy, my [minimization of substandard and gross behavior] to the contrary. But I’m here to let you know that this is not true. You are not the person you wish yourself to be on the internet; you are exactly the person you have revealed yourself as. You are not your intentions but instead your actions, the horrible garbage monster you’ve been acting like until you aren’t anymore (you can change right now…or now…still now…yup now too…honestly at any moment you could change your whole way of being and just stop treating people terribly and being ridiculous and boring and predictable and detestable. I promise). So, if you’re writing things like “DTF?” in a first message or “I want to bury myself in your body” (yes, these are super real examples), please know that that is genuinely who you are. You are not a child testing the waters, you are grown up making people uncomfortable because of how little empathy (and respect, and social awareness, etc.) you have.
I wish my advice could be as simple as “just be yourself” but apparently that’s what many men have been doing and frankly it’s not working out so great for anybody involved. So instead, my advice is to be better than your current self. I don’t know who to blame for the way you to speak to women, for the way you’ve confused harassment for honesty and the unsubstantiated sense of self-worth for quality but it has to stop.
[sidenote: if you’re a man who approaches and speaks to women in a kind and intelligent manner, well, this article obviously isn’t directed at you, but then of course you already know that.]
Do not talk about your penis. From the very first moment you noticed this cucumber of an appendage, you have loved it. It has been your best friend, your most cherished possession, and at times your greatest accomplishment. But this is an illusion. No woman will ever love your penis the way you do. Your penis is more boring than a sober academic. Not my penis! I can hear you shouting. Yes. Your penis. It’s boring and tedious and, if I’m being honest, your penis is exactly like my apartment in that we all wish it was bigger. Unless your dick is more like my student loan debt inasmuch as there’s always just way, way too much. Jokes aside, given the data on the female orgasm—something like 75% of women never reach orgasm through penetration alone, 10-15% never reach orgasm at all (omg ladies I’m so sorry!), leaving only 10-15% who have the potential to get off straight from the D (though to be clear that’s just the possibility, it might not be every time and/or with every D)—So like what are we even talking about here? How illogical do you have to be (or how totally unaware of the realities of sex) to think your dick matters? Dicks are basically worthless (not to be confused with men being worthless because obviously not). What I’m saying is that men need to stop buying into the hype that your dick is the part of you that matters. It’s only a tiny part of you, and honestly, I’d rather hear about your degree in Journalism, or your passion project, or your relationship with great Aunt Susan, or what you ate for breakfast (which should tell you a lot because I’m guessing your morning meal is pretty fucking boring).
But if not straight up dick talk, what can I say to interest her?
Interesting people are usually curious, so ask her about her life and then when she asks about yours, go ahead and tell her. Listen when she talks, act as if she may have experienced something of value or even that her very experiencing of something may have given it value. Be empathetic and kind. Don’t talk about your penis.
Try to find a common interest. Does she like wizard jokes? Does she collect Labyrinth memorabilia? Is she crushing a fantasy football league with her team “The Bad Reviews Bears”? Ask her. Have you asked her? Fucking ask her! Once you discover something in common, run with it. Even if it’s something as silly as you both like to attend Kraft Singles events (which I’ve heard are very cheesy). Turn that common thread into a conversational sweater and knit something warm together. Don’t talk about your dick.
When she asks you about yourself, be honest and self-aware (you don’t need to be your own hype man, your actions and accomplishments will speak for themselves). If, when you attend parties, people don’t congregate around you in an orbital bliss of laughter—do not claim you have an amazing sense of humor (your sense of humor is average, which isn’t amazing but it’s fine, I’m sure you have something else going for you, I mean don’t sweat it). Don’t say things like “I’m young at heart” or “I don’t look my age” because your heart has been slowly dying since the day you were born and honey, in regards to your age, if you have to say it—you aren’t it. You know why babies never get up in your face to tell you how youthful they are? Because their shit filled diapers and chubby cheeks do that for them. The same rules apply for your face. Also, those pleated khakis already gave you away. Stop giving yourself medals for kindness (to be totally honest, we’re all varying degrees of asshole and the only thing that makes that tolerable is our ability to admit it, so rather than pretending you’re the King of Benevolence because one time you didn’t act like a total psycho when someone rejected your advances, maybe just be real about who you are). You know that cliché saying “nice guys finish last”? It’s not true at all. Nice guys finish first all the time, people fucking love those guys. Entitled jerks who lack self-awareness finish last though (those dudes are the fucking worst amirite? Yuck!).
Now, I know what you may be thinking: How on earth am I going to let her know that I’m sexually attracted to her.
If you’re contacting her on any website or app that is sex/dating related, just assume she already knows this. No one who isn’t completely ridiculous is trying to make friends over on Plenty of Fish or Tinder (and if, by some stretch of the imagination, that did happen, those people usually say it right off the bat). Men often complain (to me—why do they keep thinking I care about their gripes? Like I’m some kind of wish fountain for subpar strangers?) that women on apps like Tinder are all just looking for friends, but I’m going to keep it real with you. While that’s obviously a possibility (anything is possible, I mean we live in a world where men think saying “nice tits” might actually get them somewhere), it’s unlikely. What’s more likely is that there was a possibility of attraction (again my god! this world is so full of possibilities!! Ahhh the excitement!!) that said dude then completely smashed to bits by being unimpressive (at best) or offensive/misogynistic (at worst). So like I said, if you’re having a nice conversation with a woman online, know that she knows you’re attracted (or that it’s at least in the realm of possibilities). Save the “nice tits” talk for when you’ve managed to see them for the first time. Because that’s the thing about sexual comments, context is key. A stranger talking about your body online is creepy as fuck, a man talking about your body the first time you show it to him is delicious.
This may come as a surprise but you don’t have to dehumanize a woman to have casual sex with her (in fact, if you were any good at sex you’d likely already know that the best sex happens when people feel comfortable and relaxed enough to really be themselves and, for lack of a better phrase, let it all hang out). Also, please don’t confuse a woman wanting to have casual sex with the idea that a woman who wants casual sex will definitely want to have it with you. I love casual sex (Big Fan! Huge!) but I have to be attracted/interested in having it with someone. It’s not just a first-cum scenario. You have to be brilliant and hilarious and interesting and kind and socially/self-aware, it’s a whole fucking thing.
That said, if you’re contacting a woman on ANY other website/app, well I mean you probably shouldn’t be trying to get at her in a sexual way. I mean, would you show up at your doctor’s house for a prostate exam? No, so why would you approach a woman via Twitter where she’s trying to make a name for herself writing jokes or promoting her new startup in a sexual way? If your interest lies in her as a person than talk to her like a human being. Honestly, you could just support whatever she’s doing because it’s amazing and interests you, and you could just never impose any other desires or expectations on her, ever. I mean, you can really do that, speak to women for no other purpose than they’re doing creative and brilliant things that you find interesting. It’s okay to just support and value someone. It’s okay to just be a human being with empathy.