How to Ask Out a Woman if You Really Like Her, and Also How to F the S Out Of Her Brains

Here's what women want. Really. Do this.
Publish date:
October 15, 2012
romance, how-tos, M, Sex,

Because I am determined to fuck out the memory of the guy that I thought I really liked -- but I don't want to rack up any new lovers -- I reached out to another old friend who I've known for like 15 years, who I thought might have suggestions on finding a new apartment in the next two weeks, but then when I heard his voice on the phone, I found myself asking, "'s your sex life?"

"Do you always start conversations that way?" he asked.

"No," I said, "but I'm going to start."

He didn't have any apartment suggestions, but he did book us a room at the Holiday Inn. Because I have zero feelings for this guy -- outside of friendship -- and since the No. 1 exciting thing in sex for me wasn't present (the possibility of true love), I figured I'd go the Bacchanalian porno fun sexy-time let's-do-this-fucking-thing-route; I asked if he had any fantasies.

"I'm your secretary?" I asked.

"Yes," he said. "Room 205."

"Sorry I'm late," I texted him.

"We'll discuss it when you arrive," he said.

And then we proceeded to, you know, do that whole thing. Except I kept making him laugh by suggesting things like, you know, making Outlook appointments so I could S his D, and what not.

"I'm just very client-focused," I said.

"That's good," he said. "I like how solution-oriented you are. You really know how to think outside the box."

"Yes," I said. "Can I show you certain skills that aren't listed on my resume?"

I know. I'm an idiot. Whatever. It was pretty fun, though. And then, because I try to pay it forward, I thought of a few girlfriends I could set him up with, because he is a catch. Just super not ever someone I would ever end up with. Which led me to ask...

"Maybe I could be with you?" I said.

"Are you kidding me?" he asked. "I'm way too square for you. You would go crazy. Stop being a shapeshifter. Just be yourself."

"OK," I said, "so then what advice would you have for me then? Life-wise? Man-wise? Sex-wise?"

"Hmm," he said. "Sex-wise, just keeping kissing the way you do. Life-wise, I would know your worth. That's pretty much it. Don't try to be anyone different than you. You're great."

Then he looked at me, and said something I don't think he was even expecting to ask. "I want to ask you the same. What about me? Do you have any advice for me?"

My eyes lit up.


"Yeah," he said. "I don't ever have conversations like this. Tell me whatever you want to tell me."

So I'm going to lay out for you what I told him, and I want you to keep in mind, this is my best advice. If every man did this, oh, man. It could be really great. It could. Just, yeah. And this is me. I know many of you will disagree -- and I encourage it, actually. Let's make this a resource for The Mens.

1. If you are not in college anymore, then fucking actually ask a woman out.

Know how when you say, "What are you up to? How are you?" Yeah, stop that shit.

What, are you afraid of getting rejected? Get over that, dude. Go for it. #YOLO, right? Seriously. Life's way too short. Women are going bankrupt on their motherfucking Brazilian waxes for you motherfuckers, so pony up some courage and ask us to dinner already. If you don't have money, then make it a romantic dinner at your place. Or something. Also, the first three dates, pay. Even if she does the reach-for-the-wallet fake-out. Serious.

2. Here's the magic formula to ask a woman out.

Do a firm, decisive ask. Not, "We should get a drink sometime." If you are a guy who makes a woman ask you out, there's something fucking wrong with you. Love and light and all, but that often means you have serious commitment and decision-making issues. If a commitment to a single time and date and location for dinner is too much to handle? Oh, boy.

I also get turned off by the request for just drinks. Like, dude. Invest $100. If you actually like her, fucking do it. So here's how:

"Hey [Woman], I'd love to take you to dinner on [Specific Date and Time Next Week] at [Specific Nice Restaurant Where You Will Then Make a Reservation]. Does that work for you?" Specific. This is a major panty-peeler.

Confidence. Knowing who you are. Being able to ask a woman to dinner. THIS IS HOT. Shows you are going places! You know yourself! You are a man of action! You are getting shit done! You are your highest self! Hooray for YOU, dude! If she says no? Whatever. On to the next one, you know?

3. If you really want to impress her, then do something small and thoughtful -- and it doesn't have to cost a thing.

Know what makes women go crazy? Thoughtfulness. Showing you are thinking of her. That you invested a little time thinking about her. That you anticipated and thought about what she might like. Buy her an iTunes single that made you think of her. Take a picture of her and then develop it and give it to her next time you see her. Give her a beautiful stationery pad if she's a writer. Thoughtful. Small. Women. Love. This. Shit.

4. Ask about her.

Ask her what she's thinking. Don't be a faker. Really be interested. Engage. Don't make it all about you. Show your value. Show how you are a value-add to her life. If you see her as a value-add, then put your best foot forward. Don't call it in. And also: Oh, baby, be in the moment. Have fun. Wheeeeee, right?

5. If you get to the point of physical contact where that is appropriate, the most erotic things of all are often hardly even sexual at all.

I swear to God. Do you know how many years I've spent thinking about a light touch on my back? Or a stroke on my cheek? Or a finger on my mouth? Read the "indicators of interest," as old "Game"-boy Neil Strauss calls them, and use your gut. Be able to tell if a chick is into you. If she's cold and her body language indicates she is not into you at all, then don't do the touching bullshit. But test it out. Touch her arm. Stroke her hand. Ask if that is what is indicated.

6. One of my favorite moves?

A man interlocking his arm in my mine and walking down the street that way. All gallant and chivalrous-like.

7. Just ask, if you need to.

Just say it. Nothing is that scary. Just say, "Can I kiss you?" Then when you go in for the kiss, be slow and teasing. Not like a darting gnarly tongue monster. Confident. Teasing.

8. Teasing.

Can I say that one more time? That is one of my favorite things in the world. There's something about the erotic push-and-pull that is an incredibly heightened connection. Power dynamics and control are inherently erotic, so indications and offerings of small actions to create elaborate fantasy in a woman's mind is incredibly powerful.

9. Kiss the neck.

Oh, God, do I love getting my neck kissed. And then my chest. And my whole body.

10. Women love to feel desired.

I'm a narcissist. But I think we all have elements of this, yes? To feel like a man can't get enough of you is such a turn-on. But in a confident, non-needy way.

11. As my friend Sam Lansky says, "The best relationships are when you both think you're dating up."

So, yeah, I'm a fan of playing within my league. I'm not a 21-year-old supermodel. I so get it. I have the most fun with someone who I'm very attracted to but who is attainable, especially when he feels the same way about me. Unless it's, like, Brad Pitt at that exact moment in the '90s when he's doing the little cowboy dance for Geena Davis, I'd rather not waste my time with someone who feels like they're doing me a favor.

I'd employ the same thing with women. If she's a super ice queen who's having none of it, you know, on to the next one, dude. Find someone who's feeling it.

12. If there is the possibility of love, oh my God that is crack.

I've identified this as the No. 1 thing that turns me on about sex. Emotion-free sex is pretty meh to me. Fun and porny may be physically satisfying, but yeah, how great is it to date and have sex with someone who you love and care about? That's what I'm seeking. It'll happen. But as I realized with my friend last night, "I think I need to have that sense of hope even if there isn't a man to pin it on. Just have a sense of knowing." He got it. I did, too.

13. If she says she likes things, do them.

For some reason, I get very turned on by the idea of subjugation and also the indication that I might be giving head while I'm playing with myself. So, I told my dude last night to kind of play with his finger on my mouth, teasing me as I fingered myself to orgasm. I had to tell him this several times. This is a no-no. Get it. If she likes it, do more of it. Integrate it.

14. I'm also a total cliche of a daddy-issues girl, so I like saying, "I'm a good girl," and, "I'll do a good job for you," and all that stupid bullshit.

Unless it totally skeeves you out, then engage in whatever her perversion is with her. Be a fucking champ. Be a sport. Have fun. It's sex. Yay.

15. I'm also a huge fan of romantic sex.

Doesn't have to be dirty and kinky and perverse and role-play-oriented. Be fucking romantic. Tell her why you like her piercing eyes. Say if you think about her. Do it up, baby.

16. Learn how to a finger a bitch, would you?

So many men do not know how to do this. Take a course at OneTaste. Watch some porn. Google it. Have a woman show you.

17. Confidence is everything.

I like to be pinned down and feel the force and power of a man. That's obviously with a partner that I trust and like and have indicated I want him to do this by telling him this. Ask her what she likes. Ask if she likes to be spanked. Ask if she'd like to be blindfolded. Maybe not over first drinks, but you never know. Women are some horny bitches. They're reading and re-reading "50 Shades." Sex is such a fun playground.

18. Talk to her.

Ask her what it turns her on to hear you say. If you are nervous or uncomfortable then just say what you are doing. If it's dirtier sex, then maybe, "Do you like sucking my cock?" If it's more romantic, maybe, "You feel so good; I just want to be inside you forever." Whatever. Women are such mental creatures. Much less visual. We like to be mindfucked. Or I do. Not all women. Me, and several friends I have. How's that.

Other tips? Ladies? Feel free to totally disagree with me. I welcome your impassioned rebuttals!


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