Sex Advice From Friends With Benefits

In honor of Hollywood's new favorite relationship, we sat down with some real-life FWBs.

Taylor, 29 & Winston, 29

How did you guys meet? How long did you know each other before the “benefits” began?
T: On OkCupid. One month. We started with the intention of being friends with benefits. 
So, in the movies, here’s how this goes: you’re both "over love" because you’ve been dumped or you’re just bad-asses. And then one of you, usually the girl, falls in love and the whole thing falls apart. What makes you guys different?  
Feelings will always develop beyond the initial boundaries set in a FWB situation. Let’s be honest: what’s a true friend you enjoy having sex with? A girlfriend. But, to make a relationship really work, you need that little something extra, the spark, and we don’t have that. The real difference for us is that we know that.
T: Winston and I became very close friends, so naturally I did begin to have feelings for him. I value his friendship and would much rather keep him in my life as a friend than mess it up with a failed attempt at a relationship. 

Which one of you is more likely to get jealous? Secretly jealous?
W: Well, Taylor but, since it’s a secret: [whispers] Tay — lor.
T: I fully admit it, me. 
I tell my Aunt Martha that my two friends are sleeping with each other, but that they don’t date. She says, “The poor dears! Their parents must have raised them to have some terrible commitment issues." What do you say back?  
W: "Maybe they just want to get their fuck on, Aunt M. Don't be such a cunt." In reality, I would nod and smile. I know there's nothing wrong with how I live, but the older generations look down on it. But hey, remember slavery? Old people are rarely right when ethics come into question. 
T: My parents didn't give me commitment issues — shitty boyfriends did — but really, I don't agree that participating in a friends-with-benefits relationship means you have commitment issues. My parents have a great marriage and instilled good values in me, but I don't necessarily want a boyfriend until someone who is worth it comes along. In the meantime, this is fun. 

I’m a guy, and I’ve been sleeping with this guy on and off for about a year. The sex is great and casual, but I’m nervous — the more I learn about this guy (it’s a small town), the more I realize he really sleeps around. No judgment; I’m just worried about my safety. Is it okay to ask him about the other guys he sleeps with and if he’s safe with them?  
W: Yes. If you're comfortable enough with another person to give or receive some hot hot lovin' then you should be comfortable enough asking if that hot hot lovin' is going to give you a hot hot rash. And, if you're not comfortable enough to ask a question, then you should keep your parts apart.

Is it reasonable to break up with a girl who won’t even discuss letting me try anal sex?  
T: She wont even discuss it? You need to be able to talk have an open dialogue with the person you're getting naked with, even if she's just going to say, "No, I don't want to do that and here is why."
W: I asked a girl that very question back in college. She simply responded, "Sure, let me try it on you first." That put things in perspective. But really, if a girl doesn't want to have anal, it's likely because she knows it will hurt or be uncomfortable. At least that’s the consensus. Why would you want to make someone you care about uncomfortable? Asshole.

I’m a straight woman who got married too young, and my husband and I don’t really click sexually any more. We have a three-year-old. What’s a bigger sin — cheating discreetly and keeping things together, or getting divorced?  
W: Get divorced, you nut-job. Yeah, I'm sure random people sneaking in and out of your house at all hours of the night followed by blank stares and awkward dinner conversations that eventually lead to blow-out fights are much better than double Christmas presents and rad weekends with Dad. You moron.

My girlfriend and I like to have a threesome or so a month, usually with another girl. If we meet someone out, bring her home, and sleep with her, does she spend the night? I think it’s weird to have some stranger sleep cuddled up with us, but my girlfriend always says it’s rude to throw someone out at 3 a.m., and I agree… if it’s pouring rain. Who’s right?  
T: Threesomes are about sex and only sex. Not emotional support. You don't have to be rude and kick them out but you can ask them politely to go. I can't imagine they would want to stay and cuddle. Awkward. 
W: Thank them for coming and offer to get them a car service. Sex is sex; cuddling is for cats. You wouldn't fuck your cat would you? 

Period sex — a right or a privilege?  
W: That's what blowjobs are for.
T: Copy that, Winston.

My boyfriend wants me to shave my pubic hair. I don’t. I know he’s grown up watching porn and thinks it’s normal, but it’s not, and I hate that misconception. I don’t want to sacrifice something that I believe in for him, but I also want him to turn him on. What’s a girl to do?  
W: Is that a real question? First off, it's hair — it'll grow back. Second, are you really fighting for normality by protecting your pubic hair? Third, fine, don't shave. Also, don't get oral sex. There's your sacrifice. No one wants to eat Jelly Bellys off of Don King’s dome piece.

Taylor is one half of The Urban Dater. Check out her writing here

Commentarium (101 Comments)

Jul 22 11 - 12:48am

These people are just obnoxious and so is their advice. And who on earth talks to their FWB on the phone every day?

Jul 22 11 - 3:00am

I do.

Jul 22 11 - 3:52pm

Yeah, me too. He's just kind of a chatty guy, and we don't get to hook up that often due to just life stuff (jobs, living in different areas, dating other people, etc.), so it's nice.

Jul 23 11 - 4:07pm

un-beneficialadvice is just trolling. Ignore him.

Jul 26 11 - 1:35am

THe advice is questionable but I agree, daily chat with a FWB? My FBs are human sex toys & the post-coital chatting is better when it's been a week since you've seen them.

Jul 26 11 - 3:11pm

I talk to your FWB every day too.

Jul 27 11 - 9:17pm
Your FWB

I nail your fwb daily. It's awesome. I also drink your beer.

Jul 22 11 - 1:08am

Am I the only person in NYC that thinks FWB is a crock of s--t? Honestly, what a waste of life!

Jul 22 11 - 1:42am

I don't know about obnoxious, but they're definitely not sexy that's for sure.

Jul 22 11 - 2:17pm

I'm sorry, don't unsexy people have sex too?

Jul 22 11 - 5:56pm

I'm living proof that they do. A lot. It's fucking gross.

Jul 25 11 - 7:41am

that made me lol.

Jul 22 11 - 2:13am

I like some of the advice given. Especially the should I cheat. Why would you stay in a loveless marriage? It's stupid and ultimately you'll get caught and divorce so just skip the cheating, get a divorce and have guiltless sex with whomever.

Jul 22 11 - 11:10pm


Jul 22 11 - 2:32am

the photos are weird. why are the guys' faces hidden in both photos? why is there a random solo glamour shot of the woman in the first pair?

Jul 22 11 - 8:44am

seriously agree. I think this is the first time I've seen interviews without faces on Nerve. Plus, I'm a total cynic, so it just makes me think that the guys don't want to be seen with their fwb.

Jul 22 11 - 11:14am

i thought that too.

Jul 22 11 - 1:09pm

Sorry about the face-less photos -- I agree, less than ideal. We did a nation-wide hunt to find FWB couples who'd consent to have any sort of photo -- it's hard. Most people are super reluctant to admit publicly that they're in an unconventional relationship -- and the ones who will tend to be a little nuts and/or polyamorous slave-mistresses... which wasn't really the goal of this.

Jul 22 11 - 1:59pm

Can you say how you went about looking for these people? Nation-wide on the alternative dating sites? In the more free-thinking neighborhoods of NY, LA, SF and the ATL only? FWB is such a euphemism "fishstix" highlights below.

Jul 27 11 - 9:18pm
Your FWB

From what I can tell, the chicks are pigs. The guys don't want to be assoicated with them.

Jul 22 11 - 8:35am

I have a fwb. She benifits a great deal from my pocket-book. And no sex yet! Atleast she not an ugly man-hater dyke.

Jul 22 11 - 10:31am

No sex yet? Shocking!

Jul 22 11 - 6:38pm

Sorry? FWB? What the B if you aren't getting S? Good natured conversation? CLICK.

Jul 23 11 - 6:10pm

Man, men-hating dykes are the worst! Good for you and your FWB situation, man. If I were you, I'd keep giving her a ton of money.

Jul 24 11 - 11:07am

Thanks. Only thing is I,m 48 she is 23. We,ve been hang,n out a long time. I really like her,respect her,and hot as hell 4 her! I.m sensitive to what others think,I don't deny that. Yet We have a good thing going. I.m just attracted to her,so fuck it. I.m not into all the pretentious people out at the bars end stuff. But damn,I hope she gets a job soon. I .m not into the 'sugerdaddy sfuff'.

Jul 25 11 - 2:13pm

For the love of cupcakes, you don't actually believe what you are saying, do you? You are being used. Full stop. Umbrella decoration.

Jul 26 11 - 10:24pm

Grace wtf is up with Cheryl? Am I B'n used? Cheryl I'll pay 2 play, That's my KINK! Wann B my friend? With BENEFITS? U Intullectual BEEEEEEOTCH! Grace is cool.

Jul 22 11 - 9:03am

Do the arithmetic. Your aunt grew up in the late 60s and 70s, during which time sexual behavior was a good deal freer than it is now. If she asks about your FWB connection (a term, I assure you, that was also in use then), what she's probably saying is that her and her friends' experiences with group sex turned out not to work all that well and she's curious what you've learned from her experiences and what you're doing differently. Ask and she'll probably give you some good advice. The belief that one's own generation invented sex is a charming piece of innocence.

Jul 22 11 - 11:00am

I envy these folks. Having a FWB seems like such a mature, healthy way to enhance your daily life. Good for them! Sex doesn't always need to be about rainbows and unicorns. Sometimes it can just be about fun. It's great when sex and love are connected, but it doesn't always have to be the case. Why limit the happiness in your life because of puritanical, outdated hang-ups?

Jul 22 11 - 3:04pm

i completely agree with that! these people are brave for being honest about their relationship. it's easy to sit here and make mean comments but they are strangers who decided to tell it hoe it is. good for them.

Jul 22 11 - 6:59pm

I see no reason to lie about it. I just don't seem to have the perfect "one' right now, so this is sane, safe and you can feel pretty free to discuss anything including needs and fantasy desires. What bugs me is when people judge what others are up to in the bedroom, while possibly they themselves are thinking "Damn I wish I could do that "..or something like that... I just find with my history and relationships, this is the best thing for me right now. I have and never had ANY desire for kids,and for a great deal of my life my career as an artist demanded HUGE amounts of hours spent with that and I didn't feel like I was putting enough in on my part to anyone I was seeing to make a 'serious" relationship work. We all ebb and flow in life and with people , sometimes a fwb works, sometimes it crashes and burns miserably. I have had BOTH happen to me. In my ultimate 'dream world" I would find someone that can deal with me, my weird habits, and my desires in bed. Until then, I really don't believe that one single person can offer everything one needs in life. At my age it gets even HARDER to find a good "mate". Usually when I DO meet someone I get along with, they are wayyyy younger. No future there for us, but why let that spoil what can be enjoyed , companionship, laughs, good sex . No worries!

Jul 27 11 - 6:04pm

it's very amusing that people praise the "honesty" of the FWB situation.
as in, i honestly don't like you enough to spend time with you, but i can't lick my own twat, so until someone better comes along...

Jul 22 11 - 1:02pm

Winston is such an asshole.

Jul 22 11 - 1:59pm


Jul 22 11 - 4:39pm


Jul 22 11 - 6:39pm

Fuck you!

Jul 23 11 - 3:29pm


Jul 22 11 - 1:18pm

The advice from T & W is truly godawful. Except the anal bit.

Jul 22 11 - 1:42pm

For guys..FWB = I'll fuck you but I don't want to be seen with you.
For gals = I'll let him fuck me then he'll fall in love with me.

Jul 22 11 - 1:53pm


Jul 22 11 - 3:53pm

Wow. I'm apparently doing it wrong. Let me go try to fall in love with the few FWB's I've had over the years. I'll let you know how it goes. How expensive is hypnosis?

Jul 22 11 - 7:56pm

For the 2 couples interviewed, fishstix is so spot on it's kinda depressing. Of course there are plenty of saner people (ana) doing it right...

Jul 22 11 - 2:06pm

Winston's advice is mind-bogglingly horrible. Getting a divorce and breaking up a family rather than even trying to find an alternate outlet for sex? This guy is an idiot. EVERYONE in a marriage wants to fuck other people now and then. Its normal and nothing to break up a family over. People need sex and there is nothing wrong with being emotionally monogamous with occasional sex outside of the relationship. Absolute monogamy doesn't work very well. When people need to satisfy their normal sexual needs we should tolerate it and encourage them to be happy. We live in an age of birth control, STD tests and condoms. There is no real need to demand 100% monogamy from a spouse.

Jul 22 11 - 2:16pm

Jack, You're single aren't you?

Jul 22 11 - 11:15pm

you can't be serious that you think that constitues a healthy marriage. i pity the woman who marries you. if you don't want to be monogamous don't get married.

Jul 23 11 - 4:46pm

Jack, you're an ass. If you wanna screw around, just screw around. Just don't tell her. And don't let her do it.

Jul 25 11 - 11:21am

Nic, cora, and RC, are any of you actually married? Many married couples are not as monogamous as you might think from the outside. And there's nothing wrong with that. Especially if kids are involved, divorce is a much more selfish option.

Jul 22 11 - 2:28pm

Hey I didn't know slavery and friends with benefits had anything in common! Thanks Winston!

Jul 22 11 - 3:04pm

clearly you don't know how to read.

Jul 22 11 - 3:54pm

only if you're doing it right

Jul 22 11 - 2:32pm

If you need your threesome party to leave within the hour, hire a prostitute. If you pick up a third in any other way, s/he can spend the night. Why do you suddenly get to become an asshole because you're part of a couple? You don't have to go out to brunch together, but do not expect someone to wander home in the middle of the night because you have intimacy issues.

Jul 22 11 - 6:40pm

Completely agree. That's just rude to ask someone to leave right after sex. Besides, they might be randy again in the morning....!

Jul 23 11 - 8:20am

Screw you, Grover. I'd never sleep around.

Jul 22 11 - 2:34pm

Winston and Taylor are just hilarious.

Jul 22 11 - 2:54pm
kellie b

FWB is for college kids, after that, its just sad

Jul 22 11 - 5:33pm

Wow, I have the same opinion about texting.

Jul 22 11 - 6:41pm

Wow, I have the same opinion about posting comments...

Jul 22 11 - 11:16pm

wow, i have the same opinion about kellie b

Jul 25 11 - 6:35pm
kellie b

wow, i have the same opinion about sydney

Jul 22 11 - 3:03pm

To each his own. If it works for you then get it!

Jul 22 11 - 4:37pm

Agree w/ kellie b. Women just aren't built for FWB, and 95% of the women who are trying it out eventually realize that (unless maybe they're past the childbearing years, like Patty).

Jul 22 11 - 9:26pm

Hey Kellie are you at an age where your friends are getting married, are you? Many of them, esp. the guys look pretty sad actually. You're basing your opinion on the notion that everyone has to follow the same marital formula our parents & theirs did. Sorry it doesn't work in the modern world anymore.

Jul 23 11 - 4:51pm


Jul 23 11 - 3:08am

I don't take advice from blatant assholes, but when I do, I take it from Winston and Taylor. (interpret that one how you will)

Jul 23 11 - 10:56am

I prefer Publius/LiquidCourage/etc myself.

Jul 23 11 - 1:06pm

alex, it takes one to know one.

Jul 23 11 - 2:06pm

Oh, hey, Nic, Alex - I see you two know each other.

Jul 23 11 - 3:31pm

I didn't think Taylor came across as an asshole, but Winston certainly did.

Jul 23 11 - 4:47pm

thinkwritey is just trolling.

Jul 23 11 - 6:17pm

Wow, reading this made me realize just how depressing FWB is. Basically all people concerned are saying, "well, I'm fucking him/her, and I like them, kind of, just not enough to have an actual relationship with them." Shit. If you want to get laid but don't want a relationship, that's what one-night stands are for. After the third or fourth time, it's just sad.

Jul 24 11 - 7:35am

well said grace

Jul 24 11 - 11:19am

Viva la Grace! The last time I had a 1 night stand? She had THE WORST BREATHE! Iv'e been traumatized ever since. Maybe that explains my delemna. Fuk the 1 night stands. I;ll just pay 4 it If I have 2. Or paint beutifull eyes on my hand.

Jul 24 11 - 4:49pm
Boson Higgins

You could start by learning how to spell.

Jul 24 11 - 11:16pm

grace, so what you're saying it's a better idea to screw a bunch of strangers having one night stands instead of sleeping with your friend who you trust and know? bad idea. and if you're going to be having a string of one night stands i think they have a name for that, hooker. except you're not getting paid for your slutty grace. sounds like you're the pathetic one.

Jul 23 11 - 10:27pm

It's not sad Grace, you seemed to put personal preference and social "norms" as THE standard for relationships/friendships/sex partners without taking into consideration that not everyone has to live by OTHERS rules..if it doesn't work for you FINE. But don't say that it's sad without knowing the particulars about the peoples lives you judged...There's nothing sad or pathetic about what I do. It's honest. Noone's pretending it's something it's not, or forcing it into a relationship just for the sake of having sex, it's more personal than a "one night stand" . I don't DO one night stands..THOSE are , for ME, pathetic and empty. Why should THAT be something more acceptable than being friends with someone you have a genuine affection for and be able to spend time together without forcing something else out of it all. That leads to problems in my book..Alot of people seem to think that they have to be IN a relationship ,dating, married what have you to enjoy our wonderful sensual sides. The "like them, kind of, just not enough to have an actual relationship with" comment you made needs reexamination. Nothing could be further from that for me. I am in a good honest friendship with my fwbs. Call it that , or call it casual dating ,or call it poly lifestyle ,whatever..but don't call it's the polar opposite for me.. It's happy and laughing and sharing stories and having SAFE fun with someone you are good friends with. What's so fucking sad about that? Not everyone HAS to be in a monogamous situation or following the social dictations of the day . That's being narrow minded and drinking the kool aid time ! Just because it works for one person doesn't mean it works for another.. Don't judge so fast. You might be surprised..

Jul 24 11 - 11:20am

Patty, U must have a Masters in Sociology.

Jul 25 11 - 7:07am

Or a PhD in Idiocy.

Jul 25 11 - 3:38pm

no... and no need for name calling Nucking futs... everyone has their own needs and levels of needs...why decide someone ELSE is an idiot or whatever just because YOU don't agree. Last time I checked this WAS a free country..well relatively . LOL

Jul 23 11 - 11:35pm

Pubic hair is beautiful.

Jul 24 11 - 11:43am

What? In your breakfast cereal?

Jul 24 11 - 1:37am

Huh. Yeah. I guess I was reacting more directly to Taylor's comment about being in a friends with benefits thing until "someone who's worth it comes along." On a second reading, the first FWB's interviewed are a bit more traditional, whereas you and your friend seem to be more into the poly/swinger thing, so your dynamic is a bit different. To me, Taylor's comment bummed me out because before I'd always thought of FWB's as more of something you do in college where it's kind of undefined and fun, and not something you do to pass the time until someone "real" comes along.

And to me, yeah, that kind of FWB's doesn't seem too fun. On second reading, my first comment may have been a bit on the judge-y side, but when did I say anything about social norms? My generation, in my city, or at least my circle of friends, really doesn't hold those social norms you're referring to, and although most of us are monogamous, the ones that aren't don't lecture people about how awesome and subversive (is it really? perhaps 80 years ago it was, I don't know, I wasn't around then) their lifestyle is. They're too busy getting it on.

Jul 24 11 - 1:39am

Also, the above comment's by me, not Laura, I was using a friend's computer and her default is set to Laura

Jul 24 11 - 7:28pm

Damn, bitch! Get your own computer!

Jul 24 11 - 8:00pm

No period sex? Bollocks to that. What, are you gonna die if you see your/his dick covered in blood? Pppfff, bitch please. Also, shaving? The woman should definitely find an agreement with her boyfriend, but shaving it all because he wants her to, no way. Shaving causes infections, ask your gynaecologist. Sex is too subjective and personal for this shit, restrictive advice to be given. Have period sex if you want, shave if you want. You two are rather obnoxious.

Jul 24 11 - 8:01pm

On the plus side, hats off to you for keeping it so mature. I don't know anyone who's had a FWB relationship and hasn't ended up basically at war.

Jul 24 11 - 9:37pm

Well, good thing you're not obnoxious.

Jul 25 11 - 4:30am

i am miss precious
i came across your contact in this site i appreciate true friend and love to be your friend if possible because i dislike racism in a case were by distance color cannot be a barrier between us here is my email if you fell like writing to me you are free ( look forward to hearing more from you soonest.
Yours truly,

Jul 25 11 - 7:07am

Cool! You'll be hearing from me soon (in moments!). Are you a "nice girl" or a "bad girl"? Or maybe a boy?

Jul 25 11 - 9:01am

Exploring your sexuality within the confines of a safe environment, where trust is mutual sounds alright to me!

Jul 25 11 - 11:34pm

I'm so with you! I'm in a friends-with-benefits relationship right now (gotta go meet him soon, actually!) and I love it! I've never felt quite so open and free. He encourages me to let him know what's good or bad, what I want from him and he lets me know the same. So far it's nothing too strange/outside of the box - we've only been going at it for about a month - but we tried period sex this last week. I was always too self-conscious to let any other guy try it. We have an understanding - if he meets someone and calls it off, then I let him go. If I meet someone and call it off, he lets me go. Yeah, it might be a little weird getting back into the swing of just being friends, but ultimately, because we were friends for years before adding the benefits, isn't the "friends" part the most important part of "friends-with-benefits"?

Jul 26 11 - 12:33am
J. Margari

Winston made me laugh out loud with "Maybe they just want to get their fuck on, Aunt M. Don't be such a cunt" and Taylor reminded me that there are actually some cool, unpretentious women in this city (yes I know that premise is a hard one to buy). These two summarize how 20s-30s singles should be with regard to dating: honest, open, and focused on having fun without unduly pressuring the other party.

Jul 26 11 - 11:58am

Thanks J. Margari!

Jul 26 11 - 9:23pm
Auntie M

No wonder you losers have to do this. Sheesh. This is just too much to comprehend.
Remarkable that you are capable of drawing attention to yourselves by going public with this pathetic situation.

Jul 26 11 - 9:28pm
Ajax the Great

Why buy the heifer? Gene Simmons hasn't! If she wants to give it away...maybe she can't sell it.

Jul 26 11 - 10:29pm

hey, U sound cool!

Nov 20 11 - 11:44pm

I will be putintg this dazzling insight to good use in no time.

Nov 21 11 - 3:35am

Just do me a favor and keep writing such trcehnnat analyses, OK?

Nov 21 11 - 2:13pm

MlJdWq nfbbcmceihjp

Nov 21 11 - 2:33pm

mIQL74 gcwxpfnslswk