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Friends With Benefits, Foursomes And Other Messy Relationships46:51


This episode was originally released on April 1, 2016.
What if the man you love wants to break up but keep hooking up? How should you handle jealousy toward a lover's friend of the opposite sex? What happens when a foursome between couples reveals hidden feelings?
Questions about messy relationships come in to the Dear Sugar inbox all the time. This week, the Sugars revisit an episode in which they discussed a handful of these questions in rapid-fire fashion.

Dear Sugars,

I am in a friends-with-benefits sexual relationship with my ex and best friend. Our friendship is one of the best things in my life: We're open with each other, we make each other laugh, and we support each other. We both care very deeply about the other person, and the sex is connected and amazing. This has been going on for a little over a year. We were together as a couple for a little under a year. Aside from sex, our behavior isn't all that different from when we were together: We hold hands in public, we're cuddly, we see each other and talk to each other more than we do with anyone else in our lives. We try not to be very physically affectionate in public to avoid confusing friends and family though, and we definitely don't call each other boyfriend and girlfriend. Because we're so honest with each other, he knows I'm still a bit in love with him, and I know that he doesn't want to be a couple and why.

While this sounds like it could be a stressful or unfair situation because of the feelings being "uneven," I am genuinely happy with what we have. I'm sure eventually the arrangement will end, and I do know I'll be sad and will miss the physical parts of our friendship when it does.

So what's the problem? It's that I feel so much pressure to define the relationship further for the sake of others, or to move on. My friends express concern that he should just "make up his mind" or "admit that you're really a couple," or that I should date. I've attempted to date, too! But I find myself comparing my dates to the established and happy intimacy I already have, and I don't feel that would be fair to another person. I don't know what my next steps should be. Am I fooling myself that this is something that could make me happy for now? Am I setting myself up for heartbreak somehow? Is it possible to move on while staying so connected to the person I love most?


Friends with Bafflement

Cheryl Strayed: Friends with Bafflement, I think that you have a relationship with your ex. You’re essentially boyfriend and girlfriend without that commitment. I think that you need to get clear with the fact that you really do have more expectations than you care to admit.

Steve Almond: Friends with Bafflement, you’re in love with him. And to address your questions very concretely: You are not fooling yourself that this is something that could make you happy for now. It is making you sensationally happy. You may decide that temporary joy is worth what is to come. But the other questions are, are you setting yourself up for heartbreak? Yeah, you probably are. There is a power dynamic in every relationship, and especially in sexual romantic relationships. Your ex has the power to set the terms of this relationship. He is not interested in making the relationship permanent. He has told you why, and you apparently have signed off on everything but long term security, which is the biggest “but” there is in a relationship. And it is not possible to move on while you’re so connected to the person you love the most? It is not. So you’re taking a calculated risk. There’s going to be pain down the line. You can either confront that or you can step away and say, I’m enjoying what we have for the moment. But please know that’s going to come with a price.

Dear Sugars,

My boyfriend of four years and I recently decided to go on a “break.” We are both 32, and while we have a wonderful relationship (we live together and own a dog), we’re not feeling sure that we want to spend the rest of our lives together. This hesitancy led us to the idea of taking a break and ultimately dating each other as well as other people. Yes, I agreed to this.

But a few days later, my ex-boyfriend made plans to meet an old college girlfriend I had never heard of at a weekend music festival. He went to the festival and spent last weekend in her home state. He claims nothing has happened and they are just dating long-distance. I feel totally betrayed and fooled. He says he thinks we have a chance to work out, and he has feelings for me. I explained that I wanted to be someone's first choice and, even though I agreed to our current situation, I am not okay with dating him if he's dating other people. And I find it especially insensitive that he would be dating so quickly.

His reaction was that if I feel this way, that's fair, but it will really be over, and we would both need to move on. I'm afraid to end it completely because I don't want to lose him, and I worry about having regrets – i.e. “the one that got away.” I want him to fight for me. But I feel that since he already has someone else in the wings, we're not on the same page emotionally. Is this a classic case of wanting to have his cake and eat it too? I'm afraid jealousy is clouding my judgement and my self-worth, and making me forget my reasons for the break in the first place. Do we end it all now and go our separate ways, or do I try and spend time with him knowing there is another girl he is investing in?


Stuck In A Gray Area

Steve: There’s this term in congressional politics called a “poison pill” — you’ve got a bill that you don’t really want to have pass, so you put in an amendment that kills the bill. When politicians don’t want something, they find a way to blame it on the other party. Stuck, your boyfriend is trying to put the decision on you to end this relationship. For you, him being invested in someone else is a poison pill. If I were you, I would be looking back at the reasons that you felt hesitant to commit to this guy. If this experimental phase has proved to you that you want to be with him in a committed way, then you have to tell him that. You run the risk of him saying he doesn’t want that, but make that his decision. Don’t let him push that decision onto you.

Cheryl: Stuck, I don’t think you’re “on a break,” I think the two of you broke up and you’re both too afraid to say that. You’ve been together for four years. You’ve probably gone through a lot of transitions together. And I think it’s really natural to question, four years into a relationship, do you go forward together or apart. It sounds to me like you both made the decision to go on a break because you weren’t sure that you wanted to go forward together. But it’s scary and hard to say that, especially because you usually still love the person you’ve spent those years with. You still do have that question in the back of your mind – is this the one? Am I going to go out there and date other people and think, I should have stayed? And that’s a question that only time will answer. I sympathize for both of you, Stuck. But I think this relationship, at this point, is over. And you might go off into the wide world and two years later, reconnect with this old boyfriend and say, let’s get back together. But that’s not a break. That’s a decision to come back together. And so my advice to you is to let this go. Stuck, if your boyfriend wanted to be with you, he would be with you. He would be fighting for you.

Dear Sugars,

I'm a 25-year-old woman dating a wonderful man who has just started his first year in a top graduate school program. We've been dating for almost two years and are moving forward with a long-distance relationship. He's busy at school, but has been wonderful about calling me on the phone, texting me, and keeping me in the loop with his new life. Our plan is to go no more than three weeks without seeing each other and at the end of these two years, I will go wherever he gets a new job.

My issue is not with him or our relationship – it is with a woman in his program. The two of them, along with a few other men in their class, took a long trip this summer before the school year started. They became very close very quickly, and I worry that she is starting to develop romantic feelings towards him. I went to visit a few weeks ago, and I thought she was friendly enough, although some of her comments did make me uncomfortable. At the end of one night out, he told me that he was confused with the way she was treating me – that she was not being very friendly and behaving oddly towards me. Of course, this upset me, but he reassured me that he would talk to her and that if she couldn't be nice to me they could not be friends, period.

This was last week, and I'm back home now. I haven't brought it up again because I don't want to make a big deal out of it, or make him think I don't trust him. I trust him 100%, but this situation is still bothering me, and I don't want any paranoia or jealousy to damage our relationship. He's extremely busy, and I don't want to add more stress on top of it all. Do I ask him about it? Or do I just drop it, and trust that he is handling it appropriately?


Paranoid Girlfriend

Cheryl: Paranoid Girlfriend, I think you’re being paranoid about the wrong thing. You don’t need to worry about talking to your boyfriend about your feelings. I think that it’s perfectly reasonable. You had this conversation about this friend that you both feel weird about. It’s not just your paranoia – he also brought it up with you and said that he thought she was treating you oddly, and not being friendly. And if you want to follow up on that conversation that began when you were visiting him, by all means do. And in some ways, not bringing it up gives it so much more power. It feeds that sense of paranoia. The way to not make a big deal about it is to talk about it. The way to make a big deal about it is to do just what you’re doing – writing to us, and asking us what we think, and calculating every move – so talk to him.

Steve: I agree, and I think the terms of this relationship are somewhat skewed. In the relationship, you’re already sacrificing for him a good deal. He’s going off to this top graduate school program, and at the end of those two years, you write, “I will go wherever he gets a new job.” Sometimes that can be symptomatic of a kind of acquiescence or passivity, and I counsel the opposite here. You need to let him know how you feel.

Dear Sugars,

A few years ago, my husband and I had a foursome with our very best friends of 10+ years. Afterwards, as to be expected, there were many emotions. The one that was not expected, however, was that my friend basically confessed through a letter that she had been in love with my husband for a number of years prior. We all four talked at length about the situation, and on the surface we worked everything out and moved on with our daily lives.

Deep down I have struggled with extreme jealousy over this woman ever since. It drove me crazy when she suddenly became very good friends with one of my other best friends and she even formed a deep and intimate relationship with one of my husband’s best friends. I was very bitter toward her for over a year and we hardly spoke to each other until I couldn't handle the daily thoughts of jealousy and hurt. I initiated a conversation and we made up, and things finally felt normal again. But recently, it has flared up again because she is leaving her husband. She's been very untruthful through the whole thing, which really upset me, and she knows it. The thing that hurts me most is she makes no attempt to call or text me or mend our friendship, but she still contacts my husband, and they still have a friendship. I've told my husband how I feel and he says he has no feelings for her, but why does he continue to have contact with her when he knows it upsets me?

Is it right for me to not want him to talk to her? Am I crazy for thinking that this woman has intentions to take over my friendships and marriage? I feel like I've mended our friendship once already and I don't have the strength to do it again. Actually, I don't want to be her friend anymore, but we have so many mutual friends now, thanks to her, it makes it extremely awkward in social settings. I can honestly tell you that I am the most drama-free person and this relationship with this woman is making me feel like a crazy person.


Over the Drama

Steve: Over the Drama, this situation you’re in is a bad one, and it is very clear that this woman brings a certain kind of tumult into your life. Most of the time, you would just say, it is not tenable for me to spend time with a woman who’s in love with my husband. Especially since you guys already had a foursome and have seen one another naked, in a number of ways. It is maybe a noble thing that you were able to mend the relationship with her, but now she’s in a state of disequilibrium again. She has split up with her husband, and because she’s on her own and feeling unmoored, she’s in touch with your husband, who she finds to be a source of comfort. And she’s still in your husband’s life, and he’s consenting to that, and that’s not ok. And you need to say to your husband, that’s not ok. You need some boundaries – not out of ill-will, but to preserve what you have with your husband.

Cheryl: I am a little suspicious of your husband’s relationship with her. It does seem odd to me that he would continue to allow it knowing your feelings. I would dig into that a bit. Maybe there’s more drama in your own marriage than you suspect. But there’s no question you should step back from this friendship so you can have a drama-free life.

Hi Sugars,

I'm 37, happily married with three kids. I have a friend — 38, divorced with 3 kids — who doesn't work but goes to school and receives government assistance. She is having a non-cancerous tumor removed in a month and just found out the home she's been living in is about to be sold and she has to move.

My dilemma, and some back history: I met my husband at 18 in 1996. He was my second sexual partner. My first was a habitual cheater. My husband has never cheated. I totally trust him. In 2012, he opened up to me and we discussed fantasies. His was to watch me be with another man. We tried it. We became so much better as a couple, stronger and more in love. After three years of this off and on, he stated he'd like to be with another woman and expressed interest in my friend – the one I mentioned, who needs a place to live. I didn't like that idea. I did let him be with a woman we didn't know and it totally crushed me. He still makes comments about being with my friend, but knows I'm not OK with it, and it will probably never happen.

With that being said, how can I offer to help her and let her stay with us, knowing my husband's thoughts about being with her? I trust them both, but I feel nauseous thinking that they would be in the house together during the day with no one else there. Or is it that I don't trust them? A good friend is in desperate need of help. What am I to do?


It's Only In My Head, Or Trust Issues

Cheryl: It’s wonderful that you want to help your friend, but there are other ways to help her. If you don’t want this conflict to be there, in your heart and in your home, maybe give her a loan for a place to stay for a few weeks, or enlist other friends. First, talk to your husband. And if you still feel funny, come up with another solution.

Steve: I think that on the list of reasons that you would be uncomfortable with having somebody staying in your home, your spouse wanting to have sex with that person is toward the top of the list. This situation has reawakened an era of your life with your husband when you had very different sexual fantasies and you did a reality test. And you discovered that you’re not OK with your husband being with another woman. It is not insensitive for you to place your health and happiness, and the health and happiness of your marriage, before the concern of welcoming this woman into your home. You don’t have to do that in order to be a good friend. But to me, I would view this as a kind of invitation. Why is your husband still talking about this friend, who he still fantasizes about? Every time he mentions this, he has to know that it’s a barbed hook that’s going into your flesh. That’s an issue.

Cheryl: Talk about boundaries – that’s absolutely one that needs to be set. I don’t want to hear you talking about having sex with my friend. That’s not asking too much, at all. You have the right to do that.

Dear Sugars,

I'm 31 years old, and the last three men I dated were fresh out of serious relationships. They all left within months because they weren't ready.

A few months ago, I met and fell for a man going through a bad divorce. His wife had an affair, continuing in secret for months once it was discovered. He tried desperately to hang on for his two young kids, but the marriage fell apart. He says he no longer loves her, but his deep hurt and anger towards her are obvious.

Our chemistry and connection were clear from the day we met. He constantly told me how strong his feelings were for me. We live on different coasts, so we met up in between. I flew across the country often, and we talked or texted around the clock. He opened up to me about everything. While it wasn't my favorite subject, I liked that he felt he could talk to me about his divorce and that I helped him through it.

Last week, I told him it was clear he wasn't ready for a relationship, and he agreed. His heart is still closed, and he doesn't want to put me through what he went through — being patient, hoping someone's heart will change. He said he'll know when he's ready, and asked if I wanted him to call me when he is. I said yes.

I know he needs to do this on his own and I need to move on, but it's difficult to do that knowing that if we met a year from now or had met before his marriage, this could have been it for us. I was falling in love with him, and we had arguably the best relationship either of us has ever had. Do I have to completely disconnect and move on for now?

He suffers from seasonal depression and I worry about how he'll be this winter. I don't want to abandon him as a friend and I want him to think of me when he's ready. More than anything, we are friends, and it's difficult to disconnect from someone I care so deeply about when they're struggling.

Can I call him to check in, or will that only hurt me? Should I give up all hope for a future with him one day? Would I always be second to a woman who cheated on him? Will he ever move on and be able to trust and love again?


Hurt by the Hurting

Steve: I have a strong feeling, Hurt by the Hurting, that you are not ready to be just a friend to this man. It’s very clear that if you do try to maintain a friendship with him, it’s going to hurt you. And it’s also clear that you’re still holding a torch for him. You have a right to assert what you really need and want in a relationship, and as difficult as it is, you have to seek it from a person who is willing to give you that.

Cheryl: Hurt by the Hurting, you’re saying you want a partner who is ready for a relationship. That doesn’t mean that this is all over. It is true that this guy is too fresh off a divorce to be ready for a relationship. The cool thing is, if he decides two years from now that he wants to look you up and ask you out again, he will do it. So keep faith with that. Get your own feet under you. Go into your life. See what happens. Allow yourself to fall in love with somebody else. And hold a space in your heart for this friend that you parted with, knowing that you don’t know what’s next in your life together.

New episodes of Dear Sugar Radio are released weekly. Do you have a question for the Sugars? Email

Amory Sivertson Twitter Co-Host and Producer for New Programming
Amory Sivertson is the co-host and producer of Endless Thread.


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