Category Archives: Friends With Benefits

Advice for people in “friends with benefits” relationships.

The Friends With Benefits Vacation

Dear Rob,
My question is RE: relationship etiquette involving a “friends with benefits” arrangement.

I have a female friend with whom I have a mutually beneficial (not financial) arrangement, in which she receives some actual benefits and in return we have regular “dates”.

I am not asking re: the morality of that type of arrangement, but simply about the limits and expectations from either of us.

Specifically, if I take my friend on a vacation trip for which I pay for everything, airfare, hotel, side trips, etc. is it reasonable for me to expect to have sex with her while on the trip??

Secondly and related, is it “OK” for either of us to seek or meet other potential partners while on this same trip??

I think that you are confusing a “friends with benefits” arrangement to one of having a woman available any time you’re ready for her, and providing for her, to have sex with her.

I hate to be brutal but from what you wrote me sounds more like you “give” her things in expectation of sex.

But you don’t want a lesson about morality, so here goes:

Specifically, if you take her on a vacation you are her “date” for the duration of that trip.

I don’t think it is reasonable to expect sex but at the same time I don’t think that either of you should go to the hotel bar and pick up a “new friend” for the evening.

And based on my answer above, unless the both of you agree together that this is an “open” vacation, there should be no mingling with other people looking for a sexual side-adventure.

After all, maybe you can’t get some side action but she can… how do either of you feel about this happening?

I know that if I was footing the bills I wouldn’t want to get “shut out” at the end of an evening and I wouldn’t want the responsibility of her feeling rejected haunting me from the first night out should I get lucky and she doesn’t…

And what if she gets to have the fun of her life but you get sidelined… and she’s not even around for comfort and you hurt all the more?

And what else could happen to totally ruin an otherwise fun trip when two people go as “singles” but still have “expectations” of a “pseudo-sexual relationship” without conditions or responsibilities.

To sum up… this is a bad idea unless you’re both on the same page for the trip, you both have the same understanding and expectations of behavior.

“Friends with Benefits” always has a crushing point where the idea of the relationship leads for more expectations on one person than the other.

You are at the crux of failure and abandonment. Expect less and enjoy more. Keep the rules in the open with no second guessing.

And expand your circle of friends…. I am sure she is doing that on your tab.
Best wishes,

Friends With Benefits Breakup

Dear Rob,
I encountered your article online when I was searching for the consequences of FWBs, and I decided to email you. Maybe you could give me advice.

Okay, I am one of those women who agreed to be FWBs with the guy I met.

I met him online and it turns out that we just live a couple of blocks away from each other.

Once a week he’ll pick me up and we will hangout in his place. we will watch movies or play guitar and have drinks (but we don’t drink to get drunk, just to be sober), then later he would ask if I wanna have sex with him or “if i wanna do it”.

I already understood what it means. That’s always the scenario.

After having doing all these stuff, sex is the very end of everything.

That happened for 2 months.

Having sex with him the first time was kind of a learning experience for me (since I never had a boyfriend before).

The guy was nice and everything, there was no emotional attachment at the first time. We call each other like 3 times a week or every other night and have sex with one of those nights.

That was a nice feeling, having someone to talk to, but one of my friends told me that I have to separate sex and my emotional feelings, but later, I start to fall in love with this guy.

The worse thing is, he doesn’t call me anymore.

I learned that this guy is somehow dating someone else.

Now I feel jealous about the situation.

I can’t confront him, since at the beginning we agreed on FWBs situation – and we can date anyone we want.

I am really now on the verge of telling him what I truly feel for him because this is already driving me insane.

I really like him now, but I can say that sex is not the reason why I have fallen for this guy. I like him as a person.

He is so nice and treated me with respect. Even though maybe we never had sex and we were just hanging out or dating out, I would still have fallen in love with him.

To think that I never had a boyfriend before, and I am so happy that i am seeing him and he treated me nice.

So but then, at the end, I’m the one turning out to be a loser, since I am now emotionally attached to him, but I know he is not.

Is there any advice you can give?

Do you think I should or shouldn’t tell the guy that I am falling in love with him now?

What would be the consequences if I spill out the beans to him?

Hi Susie,
Not only have you been used but you were convinced, dishonestly, that you could separate sex from emotions.

You can’t.

It’s tough having never had a boyfriend before, and now you have this great guy that listens to you, a guy that seems to understand you… but ends the night with “do you wanna do it?”

Sex is as personal as it gets and to have to “shut yourself off” from the emotions that come along with it is unnatural.

You said “He is a nice person and treated you nice”. Another lie to yourself. Sure, he was very friendly, he got what he wanted from you: sex.

And you were willing to give.

As soon as you discovered that he was dating someone else the jealousy nerves spoke up:

“He was yours first! He should still be yours! Why is he dating someone else! Doesn’t he know how you feel!”

These are the emotions you feel… they are true emotions coming from the most intimate of encounters.

Now, though, you are on your own to deal with this betrayal and hurt.

You could talk to him, but it really won’t do any good. He’ll just tell you that you were “fu-k buddies” and nothing more.

Now he has a girlfriend he doesn’t need you anymore.

Understand that the emotional attachment you feel with him is because of two things: the intimate connection (sex) you had, and the jealousy you now feel because he has someone else.

By all means, if it will make you feel better confront him with your feelings. No emails, no letters, no phone calls, just a face-to-face talk.

He will shut you out, you will be hurt.

You have learned a hard lesson and I hope you heal quickly.

Not all guys are users, not all women want to be used.

You just fell through the cracks this time. Learn from this mistake.
Best wishes,

I Want To Date A Friend That’s Dating Someone Else

Dear Rob,
I have this friend and her name is “Girl”.
She is like my best friend but I’ve been wanting to go out with her ever since I met her but she already has a boyfriend named “Jeff” and I can see she is not really happy with him.

And if I ask her out and she says no what will that do to our friendship.
Should I ask her out or not? And if I do, then how?
Wanting to be more than just friends

Hi Wanting,
No, you do not ask her out since she’s already dating. I’d suggest getting yourself an available girl to date. Look around and stop being so focused on one girl.

Maybe, just maybe, if she sees you dating someone else, or she does break up with her current boyfriend, you can step in and ask her out.
But with her dating someone else, and you supplying the emotional support and friendship she can’t get from him, she’s got an easy life.

Always, if you want to date a friend that’s already dating someone else, you have to step back and give her the chance to miss you.
Stop being her support that she isn’t getting from her current boyfriend and if there is anything real between both of you she’ll see it and break up with the guy she’s dating currently.
Once she realizes that you’re not as available as you were, and she asks you why, you can tell her honestly that you want to be more then friends and it’s not right for you to be involved as a friend, and wanting more, while she’s dating someone else.

She will appreciate your honesty and she just might dump that other guy. But it won’t happen while you’re hanging around, that’s for sure. And to make a move while she is involved with someone is just pathetic.
Best wishes,

Am I A “Friend With Benefits” Or Dating This Guy?

Hi Rob,
I have been seeing Charlie* for about 5 months. Charlie* is and engineer and works late, which means its hard to see him regularly because of late shifts. Usually on his early days or days off we’ll get together for dinner or a drink. This results in an over night stay at his place. We have been sleeping together sexually for about 3 months and it is monogamous. I told him that I am attracted to him and his response was “I’m not looking to be in a relationship right now, but I am interested in you.” What’s that mean and how am I supposed to act towards him?

I took the comment as us being friends with benefits. But friends don’t pay for dinner or drinks every time and refuse to take money when someone offers to help out with the bill. I am very confused with how he treats me. I am really into Charlie* and don’t understand why he doesn’t want to be in a relationship with me. I’m not pushy with it but I need a man’s advice on what to in a situation like this. Do I stick around and wait for him to see that I am relationship material or what? Or is it a lost cause and should I just remain friends?
-In a dilemma

Hi dilemma,
He won’t change, you need to.
Change boyfriends, that is.

And I wouldn’t even call him about it. You can be his big loss.

Guys that have ‘friends with benefits’ are the biggest users around. They get everything they want/need without caring how the other person actually feels. I bet you’ve had many sleepless nights wondering what’s going on while he beside you snoring away.

As for him paying the bills, that can be one of two things:
he realizes that he makes more money than you, so he pays, or
he figures it’s the least that he can do, to keep the benefits rolling in (without realizing that he’s practically prostituting you!)

You need to end this and find someone to settle down with, pronto.
Best wishes,

Questioning Friends With Benefits Relationships

Dear Rob,
I read some of the questions about the friends with benefits subject and have one myself.

Mine is a little different. I’ll call him ‘J’. We met around 8 years ago, online, we just started talking and eventually met up and became friends, the first night we hooked up but it didn’t go far. We talked a lot online and the phone, he would come over a lot and we would hook up, watch movies, he’d pass out, since he worked odd hours it would sometimes be at like 4am.

My friends all knew him, some of my family even met him. We would go periods when we wouldn’t hook up a lot and just hang out. If we saw each other out we would be fine talking as if we were friends, it was never odd for us, well at least for me it wasn’t.

Throughout the years we have both dated people, one of mine ended up serious for almost 4 years and we had a child together. After I was with this other guy I stopped talking to J but eventually did get a hold of him, told him about my daughter and stuff and he asked for a picture, I sent it, and got a response that said “she kinda looks like me, you sure it’s his?” It was kind of an odd question but I assured him yes.

We talked during my relationship and when we broke up it started all over again with me and J. He met my daughter, we would go over there and he never acted weird with her or anything.

He has done me numerous favors and anytime I call him he makes himself available to help me. Well not long ago the all time worst fear happened, we got pregnant! We both decided at the time it was not right for either of us, we were both back in school trying to get degrees, I had my daughter to handle, and mutually decided to abort the pregnancy.

He was there the entire time, went to the doctor’s office with me, talked to them about the risks and everything, for such a terrible situation he was as good as he could get! Even after, I assumed things would be different with us, but it wasn’t.

We did not have sex for awhile after, we would talk and fool around, but no sex. Of course eventually it moved on again, and we had sex. My feelings are changing for him, I am not sure how he feels at all, I mean over 8 years, we have never once spoke about that, we talk about other people we have dated and how it doesn’t work out and shit, but never about us. He saw me out once and I was talking to another guy who works with him and he came up behind me and grabbed me to start dancing, I almost took it as a sign of jealousy, but it could have just been coincidence.

I think to myself well if he wanted more wouldn’t he say so? But then again, I have not said a word or hinted to it either, so I am not sure. It’s not like he comes here we jump in bed and that’s it, he plays with the dog, we lay down together and watch tv, he’ll cook for me, we do the whole cuddling thing after, we kiss goodbye, it doesn’t seem like just sex, but I am afraid to say anything, because if he doesn’t want more, I am afraid of loosing him altogether!

I am not insecure, but I think it has just been so long with us this way, it would be weird to have it any other way. I don’t even know how to approach him about it, face to face, I could never do it! But I feel like a coward doing it through an email or anything!

So I guess I need a little advice from someone who doesn’t know us and how we are outside of our friends….what do u think?????
Thanks- Confused

Hi Confused,
I’m not sure exactly what you’re sure of losing here.

You’re seeing a guy, not exclusively, not with any expectations (in his head) and you’re not sure where this will lead?

After 8 years he knows that you’ll be there whenever he wants you!

Despite all best intentions, despite the friendship you have, he’s just not as involved in making the relationship stronger or more committed because he doesn’t have to!!
This is even truer because you don’t ask him!

Now is the time to either shit or get off the pot (to be frank about it).
You need a man in your life that will be a part of your family on a permanent basis. If ‘J’ isn’t the guy now, then you have to decide: him or someone else?

Do you keep things they way they are and hide your unhappiness with the status of your relationship?

Your daughter needs stability, not a part-time-friend-of-mommy’s that comes and goes in her life.

If you’ve gone though one traumatic experience with him (the abortion) and now your inner-self is crying for someone that will love you without conditions attached.

Now is the time to ask him about completing your relationship, making it solid, fulfilling and official through marriage.
If he says no, so be it… move on with your life. Stop letting him use you. You know what you’ll be in for, don’t you?
If he says yes, great, you can start planning a life and a family and a home.

What do you say to him? Be forthright.
“Hi J, I think that it’s time to find out if this semi-relationship is going to get more serious. I want to provide stability and a father for my little girl and I need a man that I can count on full-time to be here with me, married, picket fences, all that.
J, are you this guy?”

But you have to ask.

I honestly feel sorry for the position you now find yourself in.
But now is the time to move forward and live the life you certainly deserve.
Best wishes,