Mutual friends; sex and other issues (Relationship and Dating Advice)

Hey Guys!

So I seem to have found myself in a really messy situation in the past few days.

I have four really awesome friends who are all housemates. (I do not live with them) We will call one of them Mr. X. In the past few months I have developed a small crush on X but have repeatedly shot down the idea—in my head—of going further with the relationship due to his obvious difficulties with opening up to anyone especially females. His trust issues, previous failed relationships, as well as the current strained relationship with his housemates—partially the result of the way he treated another one of our mutual friends when he broke up with her–make me wonder about his ability to be in a relationship.

In the past few months I have been trying to figure out why I am attracted to him. I know I am sexually attracted to him, but I don’t think I am emotionally or romantically. I have entertained the thought of possibly dating him. (On a side note, I am a virgin and have decided to wait until I am in a steady and loving relationship before I have sex for the first time).

The other night I went to a party at their house and ashamedly got quite drunk—quite out of character for me. Mr X was also drunk and kept asking me to go into his room —obviously for sex. I told him that I would not have sex with him and left it at that. I ended up climbing into bed with him later that night and essentially passed out in his bed, looking rather desperate . (Thankfully nothing happened between us.)

The next morning we woke up and ended up spending hours lying in bed talking. He told me that he wanted to hang out more and that he likes me, although I’m really unsure if he really does; maybe he just wants FWB of a hook-up? Anyway, I was confused as he had never sent any signals that he liked me and is generally quite awkward around everyone even with his best friends. He told me that he wanted somebody there to touch, cuddle and talk to but that he feels awkward being that close to someone. I said that I was after the same thing, but that maybe it wasn’t the right time or that I wasn’t the right person to do this with. We both know that his housemates would not be happy if we were to start dating—or sleeping together—and we agreed to ‘see how it goes.’ He said that he is always going to be there if I wanted to ‘try’ with him. I am really worried that this could end badly, and I could ruin four fantastic friendships. I don’t know if I should go ahead with him or if it is a potentially toxic relationship and maybe he is just confused and wants a quick hookup.

Thank you for taking the time to read this rant, hopefully I can get another perspective that will help me come to a conclusion. (Pun intended.)


Dear Ellie,

Thanks for your question.

It feels like you’re saying two different things here. A part of you is saying you want to wait to have sex until you’re in a committed relationship. But then you talk about being sexually attracted to this guy as you contemplate being with him. The other piece that’s confusing us is your response when he told you what he wanted. (He said he wants someone to touch and cuddle with. Basically someone to be physically intimate with which includes sex.) And then you said that’s what you wanted as well. We’re confused. What do you actually want Ellie? That’s the question you need to really figure out.

You may be sexually attracted to him but we don’t think he’s actually looking for a serious, committed relationship. You’ve pretty much said he has difficulty connecting to people, and that he’s awkward. So why do you think he’ll be any different with you? Did he talk about a relationship? Did he say he’s always liked you? If you indeed are seriously thinking about a relationship with this guy we think you should come right out and be more specific with how you’re feeling and what you want. Typically we’d say wait, but in this case, since it’s somewhat incestuous all being mutual friends, we think it’s best he know the scoop right up front. This also means he should understand how you feel about sex. (That you’ve been waiting to have sex until you’re in a committed relationship.) It will make him think much harder about what he wants; and it will give him more reason to do the “right thing.” If he freaks out or is non-committal then you’ll know how to proceed. If he’s receptive to your “confession” then you can “see how it goes.” We don’t think it will necessary turn toxic, but even if you just date it will make things awkward with all of your friends. You need to first figure out what you really want and then weigh your options.

What do you think? Does this work for you? Feel free to ask as many follow-up questions as you’d like and definitely keep us posted. (In comment’s section below.)

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9 Comments on Mutual friends; sex and other issues (Relationship and Dating Advice)

  1. Okay guys, I need a quick sanity check here.

    My boyfriend of almost a year and I got in a huge argument and I’d like to get another perspective.

    To keep it simple, he texted a mutual female friend in regards to plans for another friend’s birthday dinner. I have no problem with that. He then proceeded to end the conversation with “sweet dreams”. I found out about it because it was brought up at the birthday, she mentioned that it really confused her and she thought that maybe he had meant to text me. So she responded “ditto” because she didn’t know what else to say. He was laughing and said he was just messing with her. Keep in mind this is a new friend of mine and his… so I really don’t think it’s cool to make her feel uncomfortable like that and I feel a bit disrespected as well.

    I have to say, I think this is a boundary that he should not have crossed. There have been other times that I feel this boundary was crossed as well, when he would make sexual jokes with another mutual female friend… which I ended by telling him that he was making her uncomfortable. But he thought she (and I) were being lame.

    I am willing to let it go, forgive and forget… especially because having female friends is a new concept to him (went to an all boys school, very much a ‘guys guy’ ect ect) HOWEVER, he doesn’t see anything wrong with his behavior in either of the instances. He thinks that I am being a jealous girlfriend and ridiculous. He says I need to look at the context of the message, he was just joking to mess with her. Okay, fine… I do believe that because quite frankly if I didn’t believe that then I would seriously question staying with him. So yes, I agree he was just messing with her. My problem is that he has crossed a boundary and it’s inappropriate. I let him know that it bothered me and he hit the roof.

    He was shouting in my face about it and getting really upset. Which wasn’t cool at all, but when we calmed down and had a rational conversation he still didn’t see why I was so upset.

    I don’t think it’s funny at all, and I very much doubt the female friends find it funny either. How about you guys? Cool to text other women who aren’t your girlfriend terms of endearment like “Sweet dreams” in any context? I think it’s not. But I would really like to hear another male perspective.

  2. @Jennifer……Thank you for your donation. We appreciate it. One request: We are happy to give our point of view, but prefer to remain neutral in the big picture. We’re sure you understand.
    To your question: The issue we see here is that he’s not trying to see your point of view, instead he’s lashing out and trying to defend himself. It makes us wonder how he’s going to deal with other issues that may arise. Relationships are hard and require a lot of work, AND compromise and understanding. Do we think texting “sweet dreams” is a big deal? Not totally, if it was an isolated incident. However, we can see why it would bother you if you are already on “high alert” with this kind of thing. There’s a disconnect going on. He truly believes this is no big deal. And maybe he’s more comfortable in this uncomfortable and undefined arena—the sexual/boundary arena— than most people. But the fact that it’s a big deal to you should make him reconsider his position, and think about changing his behavior. But he’s doing the opposite. One more point about “sweet dreams.” It’s not that it means much really, it’s just an odd thing to say or text, especially to someone you don’t know that well. He may be one of the few people who sees the humor in it. We’re not offended by it, and it doesn’t bother us the way it bothers you, but we just get the joke. There are probably a lot of other funnier ways to “mess” with her than that. Your thoughts? What’s your plan? Are you worried that you won’t be able to trust him? Feel free to ask as many follow-up questions as you’d like. (In the comments) We’re headed off for the evening but will be back in the morning to respond again. Take care and thanks again. ps. We hope you’ll share our site with all of your friends. Follow us on Twitter: @TGPBuzz. And help a fellow reader. Take a moment to VOTE on our Ask our Audience page.

  3. Hi guys,

    I’ve gotten myself into a strange situation. I was FWB with this guy, Ryan for 6 months, it ended when he wanted to take our relationship to the next level and I wasn’t feeling it. It took awhile for us to become friends again but for the past 2 months we’ve become great friends again.

    He lives with another guy that has become a friend of mine as well. A couple of weeks ago I met Ryan and his friend at a bar. We got talking all three of us and after Ryan left, me and his friend stayed there talking till closing time and kissed goodnight. I talked to Ryan about it and he seemed really psyched about it, telling me how great me and his friend could be together and how lucky his friend would be to date a girl like me. He really seemed fine with it so I thought I’d give it a go, me and his friend have been talking a lot and I stayed over at his place this weekend.

    This is where things start to get weird. The morning after Ryan comes into the room and tells us he has made us breakfast, we all eat together and later see a movie the three of us. Me and his friend go into his bedroom again to get some alone time and Ryan keeps making a lot of noise and texting his friend and coming into the room. He kept talking about the last time I was there with him. He even did a headstand to get our attention. I really don’t know what to think of this. Is Ryan jealous or does he just find this awkward? Why would he suggest that I date his friend if he isn’t ok with it?

    Then there is this other thing. Me and his friend spent the night together but he didn’t want to have sex. I could tell he wanted to physically but he stopped it and said he wanted to get to know me better first. Is that a sign he’s not interested or is he just trying to be romantic?

    Please help me shed some light on this weird threesome situation,



    p.s. I really love your site guys

  4. @Hannah………The first thought that came to mind is this: Are these guys trying to make a threesome happen? Ryan doesn’t seem jealous. He wouldn’t have suggested you date his friend if he was. However, he does seem curious, almost like he’s fishing for something, hinting around. And the other guy seems just luke warm enough to make us think he’s in on it. Of course we could be way off here, but Ryan’s enthusiasm seems a bit too over the top wouldn’t you say? The other reason we think something is going on is this: Guys don’t typically want to date, or sleep with, a woman that their buddy has slept with, especially when they’re living with the guy. They’ll do it if they really think there’s long-term potential, or if they are desperate for sex, but not typically with the guy around to remind them of the time he was with her. So that also enters into our thinking. We’d proceed with caution here. Something isn’t quite right.

  5. Audrina // May 18, 2013 at 6:16 pm //

    Hey guys! Quite a complex situation going on here…. I’ve been in a fwb relationship for many years. We took breaks every now and then, wouldn’t speak for a few months but every time we hooked up again it was like no time had passed at all. We have gone just over a year with seeing each other on a more than consistant basis, suddenly here and there became daily. He was in two diff relationships and I had been in two as well, if one of our significant others suspected something we always back each other up and there was never any other questions. Recently we had a threesome with his girlfriend, she was under the impression I wanted her and she invited him to join, first time for both her and i being with a female. Anyway other complicated part is this guy is my little girls dads best friend. Ouch huh… To top of off, I just found out I’m pregnant by fwb. We threw around the idea of terminating but I just can’t do it. He’s not going to be as involved as other dads as I don’t want him to lose his family, I know it’s foolish to put his needs ahead of mine but I don’t want my little girls father to hate me either. We have a on the low, late night, all night hang out/fuck enjoy each others company type deal. He’s got a key to my place and can come play/hangout anytime he wants.He always spends every other weekend at my place since his sons mom works, understandable why he lets her get her sleep. He says he loves his girlfriend/sons mother, why does he do this to her? Why on the weekends he doesn’t work is he sneaking into my bed for hours of fun? He says they have good sex like we do so why isn’t he home screwing her. Also last night he brought up me keeping the baby while we were having sex, why? I def thought had I done that it would have been a turn off.

  6. @Audrina……What exactly is your question? Why is he not dumping his girlfriend for you? This guy is a player. He’s cheating on his girlfriend with you. And that’s not going to change. He’d probably cheat on you if he was with you. So, we’re not sure what you want here. In our minds you need to focus on preparing for your baby. (Congrats by the way.) Hopefully he’ll choose to be involved with his child’s life. You’re right this is complicated, but only because you’re allowing it do be. Our suggestion: (And you can take it or leave it.) Move on from this. This is going nowhere. You deserve better. Good luck.

  7. Audrina // May 20, 2013 at 6:30 pm //

    What is it that he wants from me? Why does he say he has feelings for me? Why does he need to come fuck around with me after he “puts his girl to sleep”? Why does he stay at my house for hours at night just hanging out with me? I don’t expect or want him to be in a relationship with me, as I don’t want to be the one who gets cheated on. I just don’t understand why he does all this extra crap if we are only supposed to be fuck buddies.

  8. @Audrina…….Because he wants a relationship without the commitment, which includes sex AND emotional support and friendship. But he still wants the freedom to do whatever he wants. This is the worst kind of situation. You might want to rethink this. We don’t think it’s good for your emotional well-being. Maybe we already said that.

  9. Okay so i have a boyfriend “joe” whom ive been dating for a year, i love him and care for him and i know he loves me. He shows me he loves me and pretty much treats me like a princess. Today my best friend for 6 years “brad” who is a guy told me he likes me alot and he went in depth describing his feelings. Pretty much saying that im the only girl he would wAnt to marry and he has never felt this way about a girl. (Forgot to mention that over the year that ive been dating Joe, him and brad have become pretty close) anyway i told bras that i love joe and im sorry i cant return the feelings. Brad told me that his intentions arnt to break up me and joe. But that he just wanted to let me kno of his feeling and that we wont be able to hang out for a long while at least till he gets over me cuz he doesnt wanna fall more for me. (However, he will continue to hang with joe) now i feel really reallt sad cuZ i feel like i lost a friend and i dont know how to help him feel better. Do i just let him be? Or what can i say to make him feel better or to console him? Help

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