Friends with Benefits with my boss?

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Friends with benefits? 


Dear Guys,

About 8 years ago I hooked up with my boss. I had a crush on him since I started the job. About a year later we hooked up. A one time only thing because I found out he was in a relationship that I didn’t know about.

We recently found each other again and he asked about hooking up again and seeing where things go this time because he’s single. I don’t know what to do.  My problem is that I’ve always liked him and I really don’t know what his real intentions are. Is he just after a piece of ass or is he being real about things going somewhere?  I know I will get attached because I don’t just go have sex to have sex.  Should I give it a chance or run?


Dear Jacquelyn,

Thanks for your question.

The red flag here is that he had sex with you while he was in a relationship. That’s really our only concern here. If he did that then who’s to say he’s really changed? But it’s possible. That would be up to you to figure out.

However, having said that, life is about taking risks. And if you really like this guy we don’t see why you can’t explore things. BUT…we wouldn’t start off by hooking up and having sex with him. That’s a bad idea. Very bad idea. If he really wants to see where things go, suggest a proper type of courtship. If he’s really into exploring a relationship with you he’ll be open to this suggestion. If he’s not, and he keeps pushing for sex and a FWB arrangement, then you’ll have your answer.


Hope this helps.


ps. Please let your friends know about us. Thanks!

10 Comments on Friends with Benefits with my boss?

  1. This guy my friend let’s call him Houdini he’s my Boss too but at Uni. Ok so me and Houdini are clearly friends before I was in a relationship and he told me he wanted to have fun with me (spent the night that way) but had work early the next morning. We spent time talking about the fact that we both wanted to have sex with each other. (This has nothing to do with the problems me and my ex were having Houdini was just an opportunity to actually have sex in last 2 months more then once!) So anyway I freaked out and realised 1. I started to really like the guy! 2. My ex is my best friend and I was just angry stupid and feeling neglected. So anyway I called it off and so did he kind of because he said he didn’t want to use me and he freaked out about getting in between me and my ex! (how does he come off sounding nice?) Anyway I broke up with my boyfriend because look at the mess I could have created if we stayed together? And so Houdini I work with as a volunteer at Uni, he works there as staff he is 30 and I’m 25. We email and text each other a lot, we are friends we share stuff about each other but I can’t get him to feel safe with me enough to admit that he actually wants and does share stuff with me, its like he’s in denial that there is more to us then wanted to sleep with each other, which we have not done. I also get serious territorial vibes from him, like he gets jealous if I talk to a mutual friend of ours, like he’ll be quite blunt with me if I mention his name and stuff, just weird. In our last email he told me his good friend passed away in a way like he needed to tell me like I matter enough to be told this, also we don’t have to speak to each other this much as its my summer hols and I wont offic see him till October! But we have spoke minimum every single week since the hols started. So when Houdini told me about his friend I told him he could off load on me if he needed to cause I’m a listener or whatever and he said this (The whole off loading, sharing thing isn’t really my bag… sporadically i’ve been known to do !
    just tha
    t, but i’m more the just keep pressing on kinda guy, sorry if that’s frustrating! 🙂 xx) Then I said (don’t worry that isnt frustrating for me I would only want you to share something with me if you really wanted to not because I pushed you. Dealing doesn’t always mean sharing sometimes its just getting on with life 😛 x x) I mean are you kidding? I love a masculine guy, that is very sexy! Not frustrating at all lol. But I would love him to admit that he does want to share with me as he already does! Also I still badly want to sleep with him but I don’t do that with people I don’t love… he knows that so what is he doing? am I right to feel like like he’s grooming me? And if so, how do I turn the tables through email! And should I enter in to FWB with him because I don’t know why but it feel inevitable but I would rather it my choice then something he groomed me for. He is so much more experienced but I think he’s nice because I’ve met dirt bag and he isnt it..

  2. @Coco…..Your work relationship is likely slowing things down a bit. Our guess is, he probably would be pursuing you more seriously if he wasn’t your boss. (Some people don’t even like to date anyone they work with.) It’s too early to say exactly what’s going on, so we say, be patient. Just see what happens. And let him initiate any sort of dating. That way you’ll really know if he’s into you. As far as a FWB arrangement? NO, definitely do not pursue that avenue, especially if you have deeper feelings for him. That rarely progresses into anything more than sex, and then confusion and frustration. (Check out our video on our video page. Friends with Benefits.) If he’s being shy, or whatever, drop as many hints letting him know you’d be open to going out with him. But if he’s not going to step to the plate and ask you out on a proper date, then he’s not ready for any sort of relationship. Best to move on if that happens. Your thoughts? Feel free to ask as many follow up questions as you’d like. ps. And please let your friends know about us. Thanks. And if you found this helpful please consider a small donation to the guys using the PayPal button on the right of any page. No donation is too small or too big. Take care.

  3. Thank you for your answer. So it sounds like you guys think he likes me more then just FWB but whats holding him back is being my Boss. I can understand the not wanted to date anyone he works with as he’s told me he likes to keep things separate not mixing business with pleasure I guess. But he doesn’t have any qualms about telling me how attractive he thinks I am, I also didn’t realise that guys get shy like that. Its hard because I know what I said before but it is more then sex for me, I find that I care a good deal about him, it feels unfair that I feel that way but i can’t get the confirmation from him as I know not to initiate anything with a man espesh a really masculine one. But if being my Boss is that much an issue I m screwed as Im at Uni for another 2 years…how long would it usually take for a guy to make his move in a none sexual way? And yea if it progresses through his choice I will of course let you know too 🙂

  4. @Coco….To us it should have been plenty of time for him to ask you out. Sorry, this is one of those frustrating situations where you just have to wait and see what happens. Definitely keep us posted. And good luck!

  5. Hey Guys! Please bear with me; I’m trying to explain everything and it may end up being like a book!
    This was my problem… I didn’t know if this guy was really interested in me or just wanted to sleep with me. Now I feel like I know the answer, I just need someone else to confirm it.
    But anyways; so I am working at a restaurant as a waitress and throughout the restaurant we have a few managers. One of the managers, let’s call him Pryde, is 26 (I’m 20) would always teased me in little ways. I.E lightly bumping into me whenever we cross paths or (I stand with one leg locked and my hip to the side) he’d knock my leg in when he passed me. Later on, he smoothly gave me his number when another co-worker of mine gave me his number as well. Being a new hire at the time I texted him one night asking him various questions which were strictly business and that’s how he got my number. As I continued to work there we would catch each other’s eyes from across the restaurant and jokingly bully each other. Whenever he knew that I needed him to help me with something he would half-heartedly jog to the other side of the room and intentionally make me chase after him. When I pointed that out to him, Pryde would laugh and say that the chase is what makes it interesting and hope I enjoyed the field trip. I laughed back and told him that it wasn’t a trip without a lunchable.
    At the end of my shift that night I was leaving out the door (he had to stay there longer to close up the place) when Pryde texted me telling me that he would bring me a lunchable if I really wanted one. I told him I’d only want one if he was serious. We kept the conversation going and it eventually led to him asking me if I wanted to do something after work one day or even when we were both free. I agreed, because he was interesting and I slowly found myself getting attracted to him. This is where the problem comes into play; we are not allowed to have relations with our managers and if that were to happen Pryde could lose his job. He was very direct and clear from the beginning after he asked me if I wanted to hang out that I wasn’t allowed to tell ANYONE that we were hanging out or seeing each other, since people at our workplace liked to throw things out of hand. This is was his career and life at stake. (I’m sorry, I feel like I have to tell you guys everything in details because when I was trying to figure out this problem myself, I brought every one of these details into account… -___-;)
    I always kept that in mind and have never told a soul about things between me and Pryde. The first night that we hung out, I got to know a lot about him (Only because I asked though. This is weird because he told me that he liked to have conversations but I felt like I had to pull thing out of him.) ANYWAYS! He has this huge collection of movies on a shelf and insisted that I chose a movie to put in. In order for me to get a good view of all his movies I had to stand on the edge of his bed and sort of balance myself. While I was focused on the movies he lightly pushed me and I lost balance, almost falling off the bed. Thankfully, he caught me. (That not being too hard as he stands at 6’1, me at 5’1.) During the movie, he kissed me. We made out. Watched the movie. Talked. Joked. Laughed. No, I did not sleep with him.
    The next day I didn’t see him because he went out to the bar with a mutual friend of ours. His name is Greg and he works as the bartender at our restaurant. I should put it out there for you guys to know that at this time I had just recently gotten out of a relationship. It was a mutual decision and there are no feelings left over. But I was still living with the EX. So while Pryde and Greg were at the bar, somehow I was brought up in the conversation. Greg told Pryde I lived with my boyfriend. (Obviously not knowing that I was recently broken up.) Pryde then texted me saying “So I heard you lived with your boyfriend. Nice to know. See ya later.” With obvious irritation in his text I was thinking that he thought I was cheating on my ‘boyfriend’. I responded “It’s nice knowing that you guys like to talk about me, but that is false. I broke up with my boyfriend a week or two ago. Bye.” I was so irritated to think that Greg would say something like that. Pryde eventually apologized and asked me to forgive him. Me being me, I forgave him. Greg, though, was not so lucky.
    OKAY SO FAST FORWARD. For the next four weeks I went to Prydes house every night after either he or I got off work. (Mind you that he gets off work around 1 or 2 am.) When I think back to it, I realized that I only saw him at his house and at those odd hours. Although it’s not THAT odd because that’s when he got off work. So four weeks in and we’ve slept with each other twice, but before I ever slept with him I told him that I didn’t want to because I didn’t want to get attached… Let me tell you guys something about Pryde, he does not express his feelings or say anything that would let me know how he’s feeling. At least that’s how he is with me; I cannot tell you how he is with other people. After I said that to him, I felt like he was offended or a bit irritated. He didn’t say anything but that’s the air I got from him. One thing to another, we ended up sleeping together twice (different days). From the start of this whole ordeal between us I was a bit iffy of his feelings for me. At this point I have already put it out there that I liked him. (Not face to face though, although I should have. It was through text.) Just reminding you guys that Pryde does not share his emotions so he definitely did not tell me he liked me either. I seemed to read too much into his actions, the things he did for me were always sweet when we were physically together. For example, when I had a really bad day at work or just felt really down, he would play his guitar and sing for me; it always picked me up instantly.
    There was a time when I was trying to get him to say that he wanted to see me. DIRECTLY. Since whenever he invited me over he would say something along the lines of “If you want, you can come over after work/after I get off/later.” Somehow the conversation went along the lines of me telling him I would come over. Him telling me he was tired. I promptly responded with an ‘I probably won’t come over then’ because he said he was tired and that I would just go home. He short responded with a ‘Fine.’ I then quickly asked ‘Unless you wanted to see me?’ To which he angrily answered with ‘If I didn’t want to see you then I wouldn’t have invited you over, instead you would rather go home to your EX rather than hanging out with me. That’s fine though, have a nice night.’ I obviously caved and went over there that night. Whenever I go over to his house I’d end up staying there until maybe 6 or 7 in the morning, leaving around that time to go home to sleep myself, since Pryde had already fallen asleep an hour earlier. (I had work the next day.) I honestly don’t know if he took offense to this because he never said anything, but he’d tell me to sleep there and I always insisted that I had to go home. For reasons like I didn’t want to wake up and use his shower, I didn’t know how he’d react to me using his shower. But when I was leaving he would never try to stop me, causing us to part on angry terms.
    A month and a half into this dysfunctional relationship, he stopped teasing me at work. He barely even spoke to me, which bothered me. So I stopped texting him, here’s another thing I ALWAYS text him first. ALWAYS, and at first he’d respond in a timely manner but as the days went on he slowly took forever to respond. I don’t when to mention this but I feel like it’s something I should explain too.. There was a time where he cooked for me as I fell asleep on his couch, when he finished cooking I woke up and told him I had to go home. Am I feeling bad about this for no reason? Or was that just rude of me..? He did express his anger about me leaving when he went out and bought stuff to cook for me. I apologized and told him I would make it up to him and cook for him. Okay, back to me deciding not to text him anymore. I didn’t talk to him for a week, even ignoring him at work. I caved.. again. I texted him to see how he was doing, he said he was fine. He even ended up inviting me over to his place again. That night when I went over though, everything was completely different. He was more affectionate than usual. He cuddled with me and kissed me first. We did end up sleeping with each other that night even that was different. He held me around the waist as he kissed me, I felt so secured. After the deed was done, he and I started to fall asleep, in which I fell asleep with his arms around me. Leaving his house that morning, the terms were nice and happy.
    Three days later, he texted me telling me that management and half the staff thought we were dating. He argued that he never told a soul, meaning it must have been me. I’m being honest with you guys, the only person I told about me and Pryde was my younger sister who had no relation to my work life at all! She’s never even eaten at our restaurant. I argued with him trying to defend myself, but to no avail. He was dead set on it being my fault. He even said “My career and life is at risk for something that isn’t even true.” He ended everything between us right then and there. I don’t understand how it got out, like I mentioned before we both stopped talking to each other at work a couple weeks after we started seeing one another. Now at work, he’s a huge douche to me (yelling at me for things that he wouldn’t yell about to anyone). Rude to all the girls and only talks to the guys. I’m even really close to looking for another job because it’s awful to like him this much and have to see him every time I work. The weird part to this is that our general manager and no other coworker has even come up to me and asked me about these rumors between me and him. So a part of me thinks that he made it up because he got tired of me and didn’t know how to end it in a different way.
    Guys, was I just a fling or did he really have interest in me? I honestly feel like he only saw me as a fling, but Pryde has never admitted I was or said I wasn’t. So my head keeps wondering if there’s a possibility that he liked me. To begin with I would have been okay if he had said he only wanted to be FWB, at least that way I would have known where my emotions should stay! Please! I need you guys to tell me what you honestly think is going on in his head. I have already settled on him just using me, but for some reason I need a guy to tell me what’s up, in an unbiased view.
    So sorry about the book I just wrote for you guy! Haha. So many thank yous though!

  6. @Lala….We hate to agree with you but we do. But maybe not in the extent that you feel. Obviously he liked you and thought you were fun and interesting enough. And he must have been physically attracted to you because his main goal was to sleep with you. But you know, it may not even have been that manipulative. It may just be that he wanted to have fun with an attractive girl, and you happened to be the one who fit the bill. It happens all of the time. Try not to beat yourself up over it. And you know, he’s showing his true colors now. He made up some excuse about why he couldn’t see you anymore—yes, we think it’s an excuse too; maybe there’s a small part of it that’s true, but he embellished for sure—and now he treats you like crap, along with the rest of the employees. And think about it Lala, what kind of boyfriend would he really be? Maybe he was fun, but it sounds like he wasn’t much of a conversationalist, and maybe didn’t even have much to say. Maybe you don’t care about that now, but believe us, it would drive you nuts in six months or six years, or whatever. So yes, this was a fling for him, and for you. It’s time to move on to more interesting things. Does this help? We hope so. Feel free to ask as many follow up questions as you’d like. And keep us posted. ps. Please share our site with friends. We appreciate it. Also, we’re relaunching in a few days, and we’ll be relying on our Audience to give input about questions with a multiple choice poll. We hope you’ll come back and bring your posse too! All the best.

  7. Hi guys! I’m in a bit of a mess here. Here’s the deal, I’m FWB with my boss. It started out really friendly between us and if I would be honest, I had a crush on him from the day I interviewed for the job. We’re in advertising so it’s pretty normal to have drinks after work and since we’re both probably the only people in the office who could drink ourselves until next morning and still show up at work on time and deliver great work we would often end up drinking together or be the only ones left. We would often drink together which became an almost every night thing and we became really close since we’d talk about anything and everything. From work to life to relationships to family to friends to goals and frustrations and what not. Then sometimes when we have time to spare we would go out for coffee during the day as well. We became really close though it never seemed to affect our relationship at work. And it went on for about 6 months. But outside of work though, sometimes he would be a bit flirty or would pop leading questions. People we meet when we were out would often ask if we’re together. And we’d just laugh and I’d say he’s my boss and he’d say I’m his boss.
    However about 3 months ago, we were too drunk that soemething happened between us. And when he was taking me home he wanted to talk about it but I said I don’t want to talk and that we should just forget it ever happened. So we went on with our business as though nothing had happened. A month later we both had to come to office and work on a weekend for an Ad we needed to rush and release the following week. We finished quite early (around 4pm) and decided to get an early dinner which turned into an early drinking session. Then his best friend and and best friednd’s wife joined us which lasted 1 in the morning. So when we were all going home, he said he’ll take me home. And the thing that didn’t happen happened again. And this time he was the one who asked to keep it between us.
    And when it happened again for the third time, he said we really need to talk about it. So I said, it’s just physical between us. No strings. Then he asked, “For now?” I said to him that a relationship between us will never work. For one thing, he’s my boss. And he’s twice my age (he’s 46, I’m 23). So he agreed to be FWB. And we set the boundaries of our arrangement. (never in the work place, etc)
    However, after our out-of-town company planning event last week (which was a 3-day business/vacation trip in an exclusive resort) he started acting weird. On the trip home he was asking me to ride with him on the trip back which I declined. (It’s a four-hour drive and our car arrangements were arranged by the HR people.) When we got back, he asked me to spend the night over. To which I agreed because trying to keep our hands off each other during the 3day event at a very romantic place created a bit of sexual tension between us. Then that night he started sweet-talking to me. And his “I love that you’re…” and “I like your…” started sounding too close to I love you and I like you. Which I dismissed as an after-effect of the amount of self-control he needed to get through that planning. But then that night he was cuddly after sex and I was too dead tired to react. The next day he took me out for coffee and movie and spent almost the entire day together. By then I was panicking already and I asked him if our arrangement is still clear. He said yes. But then he’s starting to get too familiar even in the office.
    I really don’t know what to do. His actions are starting to confuse me. On one side, it’s freaking me out that he may be starting to get attached. On the other, I’m starting to like his attention and I’m scared that if this goes on I might get attached. What should I do?

  8. @Crimson…..What you should do depends on what you want out of this? And since you’re a bit confused about exactly what that is, the rest of this situation is even more confusing. We would agree that it seems he wants something more with you. That’s a nice surprise to us. Usually the older guy—the boss—just wants sex with their young employee, but in this case it seems he’s developed feelings. The question then remains: Are you interested in something more with this man? If so, then there’s nothing to do except go with the flow and see what happens. (No guarantees of course that it will work out. And no guarantees that work won’t get a bit messy) If you don’t want more than a FWB arrangement then we’d advise ceasing all activity even remotely related to sex and/or dating. (Sex, drinks, coffee, hang outs, etc.) We’re kind of thinking in extremes here. If you’re interested, then go all in. If you’re not, then you need to be all out. What do you think? What are you leaning towards? ps. Please share our site with friends. Thanks. We appreciate it.

  9. My boss seduced me to have sex with him. He went after me tirelessly, calling me after working hours and asking me out for late night drinks. I relented. Slept with him for a whole year, found out about his gf and now he accused me of seducing him. Bad idea to sleep with your boss.

  10. @Cordella……Thanks for sharing your experience.

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