“Remember that you’re not doing this out of compatibility or spirituality or anything good. You’re doing this because you’re not supposed to. Accept your guilt.”
Any Fling is Possible
There’s a saying in sports: On any given day, any team can win. Even better, in our humble opinion, we believe that you can bang any girl.
We don’t care if she’s married, a swimsuit model, or the girl you dumped by text message last year — she’s fair game. And as long as you’re willing to take a few risks, you might actually have a chance with her. Here’s our handy guide to improving the offs of getting off with an off-limit girl.
The Fling: TAKEN
Assess the situation:
It’s obvious why this is verboten — even if you’re not technically cheating, you’re still breaking every code in the book and risking as ass-whooping from her man. That said, it’s easy to spot and interested candidate. “If a married woman is going to meet you for coffee, or go to a movie with you, she is interested,” says comedian Robert Kelly, co-author of Cheat: A Man’s Guide to Infidelity and host of the “YKWD!” podcast on RiotCast.com “You just need to give her the excuse she needs to be the piece of shit she wants to be.”
Abort the Mission if:
She tries to take you home. “If she invited you back to her house, she’s trying to get caught,” Kelly says. “Make sure this isn’t some crazy thing to get her husband jealous.”
Seal the deal:
The key to success is letting her believe the whole thing just happened. Don’t verbalize the attraction — it’ll give her too much time to talk herself out of it. Instead, let her vent about her man or reflect on her hopes and dreams. “When it finally goes down, it’s going to be quick and dirty and evil,” Kelly says.
Kiss and tell?
Wait a few months — and even then, tell only close friends.
The Fling: YOUR EX’S BEST FRIEND
Assess the situation:
Depending on the circumstances of your breakup, sleeping with your ex’s best pal can be sweet revenge or a total douche move. Either way, it’s fun. But you’re playing with a handicap, because in one way or another, you’ve been a source of misery in her friend’s life — either you broke her heart, or you annoyed the shit out of her until she dumped you, or you were perfect but there just wasn’t any chemistry. Whatever the situation, her best friend has heard every grisly detail and probably knows more about you than you realize. Are you okay with all that? Then proceed.
Abort the mission if:
You ripped your ex’s heart out. If her best friend is still willing to sleep with you, assume she either has an ulterior motive (e.g., webcam humiliation) or is a borderline sociopath.
Seal the deal:
This might be easier than expected. “There’s a weird psychological mechanism — women tend to be attracted to the same person their friends are,” says Mark Manson, self-development expert and creator of PostMasculine.com. “Expect hesitance from your ex’s bestie — chicks before dicks, remember? — but it can be done.” Play the wounded-puppy card or the “I kinda wanted you the whole time” card, then lay low and wait for her to get the proverbial permission slip signed by your ex. You’re in.
Kiss and tell?
Zip it. Let her spill the beans.
The Fling: YOUR BEST FRIEND’S EX
Assess the situation:
There are few women more out-of-bounds than the one your best friend used to bang. (Kelly compares the thrill to “seeing a tit for the first time — you know it’s something you’re not really supposed to see.”) But before you make your move, evaluate their breakup. If they dated casually for a few months, you’re cool. “If they lived together for four years and you ate Christmas dinner with them, that’s a different scenario,” Kelly says.
Abort the mission if:
Your friend is still single. “He can’t be lonely and searching while you’re fucking his old chick,” Kelly warns.
Seal the deal:
If you always got along with his ex, bump into her and let things unfold. If she never liked you, you’ve got intrigue on your side — she can get wrapped up in the taboo of fucking someone she used to hate. And even if you spent the tenure of their relationship urging your friend to dump her, tell her that you think he was crazy to let her go.
Kiss and tell?
“You shut your face,” Kelly advises. “The only person you can tell is your son on his 30th birthday.”
The Fling: YOUR EX
Assess the situation:
The good news is, you’ve already paved the way. “Sexual access to exes is always fairly open, but the mechanics depend on who dumped whom,” Manson says. If she dumped you, make sure you’re 100 percent over her emotionally. If you dumped her, make sure you’re not just being an asshole — or at least make sure you’re okay with being an asshole.
Abort the mission if:
She wants to get back together. “Don’t be cruel and string her along,” Manson says.
Seal the deal:
Wait until the wounds have fully healed for both of you, and be up-front about your expectations. Are you looking to reconnect? Find a fuck buddy? Just get your rocks off? She’s been with you before and sees through your bullshit, so honesty is the best policy.
Kiss and tell?
Sure.
The Fling: YOUR BOSS
Assess the situation:
Are you working at your dream job, with amazing coworkers and limitless growth potential and a fabulous benefits package? No? Then you might as well try to fuck your boss. Sure, you’ll be gambling your job — or at least your professional integrity — on the conquest, but this is Sexual Bucket List territory.
Abort the mission if:
You get the vibe she’s a power-trippy psycho who’s going to call you into her office every day for extra credit.
Seal the deal:
This is the meeting of your life, so for the love of gainful employment, bring your A game. “If you mediocre-fuck your boss — if you give her an okay fuck — you’re done,” Kelly cautions. “She’s going to tell everyone. It had better be the best fuck ever — then make her breakfast and get out of there like James Bond.”
Kiss and tell?
No — at least not at work.
The Fling: YOUR CLOSEST FEMALE FRIEND
Assess the situation:
“Chances are, you’re cemented in her ‘friend zone,’” Manson says. “Many men have died sequestered in that miserable zone and have never gotten out.” But all hope is not lost — with a little finesse, you can be the exception.
Abort the mission if:
You simply can’t bear to risk your friendship…. Just kidding. Go for it.
Seal the deal:
Trying to present a sexual relationship as the natural progression of your friendship will backfire. “Most guys try to play the ‘we’re such great friends, we’d be great lovers’ card,” Manson says. “It reeks of entitlement and desperation.” Instead, lay it on the line: Tell her you’ve become attracted to her in a more-than-friends way, and you just wanted her to know. “Be confident — say it like you’re explaining how to assemble a DVD player,” Manson says. “Don’t try to talk her into it. Give her time to see you in a different way. It’s the only way I’ve ever heard of it happening.”
Kiss and tell?
Generally safe.
The Fling: YOUR BEST FRIEND’S SISTER
Assess the situation:
This might be a bad idea, especially if she’s his younger sister. Just remember that, in the long run, what he thinks of you is more important than what she thinks of you.
Abort the mission if:
Your friend has a street-fighting background or a temper.
Seal the deal:
Dude, you’re on your own with this one.
Kiss and tell?
No!
The Fling: WAY OUT OF YOUR LEAGUE
Assess the situation:
“You have two choices: Improve yourself or lie,” Manson says. “Self-improvement is always the best route to attracting more women.” If the girl is slightly out of your league, you can probably pull yourself up to her level pretty easily — dress like a Banana Republic mannequin, buy her a bottle of wine you can’t really afford, whatever. If she’s ridiculously unattainable, however, you might need to open up to her about how hard it is to be the CFO of a Fortune 500 company — and hope no one blows your cover.
Abort the mission if:
She seems too smart to buy your story.
Seal the deal:
Hot girls are used to getting hit on by guys who are arrogant enough to think they have a shot. Basically, as long as you come off better than those douche bags, she might just give you a chance to make your case.
Kiss and tell?
Hell yes.
Compared to even just ten years ago at this first publication, the – let’s go with “dating” – landscape has changed a lot. The concept of openly meeting someone new for the express, and perhaps sole, purpose of having sex has become essentially commonplace. (Tinder was less than a year old in 2013, remember.) Of course whatever your opinion of dating apps and their place in society these days, we can still get shocked sometimes at the underlying disrespect and complete misunderstanding of women in some of these old articles. No wonder the folks who take these things to heart — rather than for the humor and parody intended — have trouble getting dates.
