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This is my first post. I'm experiencing two dilemmas right now. I've been feeling very alone lately as I feel I can't speak to my friends about something that has been happening to me. I'm in my early 20's and I've never had a boyfriend. I was always very scared and didn't feel it was necessary to date or do sexual stuff. I used to wonder if I was asexual. Recently my best friends brother has been reaching out to me. He is in his late 20's and several years older than me. We have a few things in common and I really enjoy talking with him. He started flirting with me hard core one day and I decided to tell my best friend out of respect that it was happening. She already knew because of her brother and was waiting for me to reach out to her about it. I wasn't interested in doing anything non-platonic with her brother. I told her and her brother this. She's the type to joke around, so she was laughing about how we were flirting together, but at the same time, she didn't seem to really want us to do anything together. It was very hard for me to read how she truly felt about the situation. She told her brother that the age gap was weird, but she never mentioned any of this to me. She said that if I really wanted a one night stand, her brother would probably be down. This was brought up because I was explaining to her how I never really felt the urge to sleep with someone and I was beginning to think I just needed to get it over with.

 

Her bother and I started hanging out (which she was aware of). One day we started fooling around and he said he wanted to sleep with me. He ended up taking my virginity. Now we hang out about once a week and talk daily. I feel extreme guilt because I never told my friend about this and it's been weeks. He told me that it's none of her business and that she doesn't need to know but I feel like keeping it a secret is bad. I also can see why he would say that though, because a persons sex life can be very private. I want to tell her, but she is really my best friend and I'm terrified to lose her.

 

My second dilemma is revolving around her brother. Like I mentioned, I've never dated before. I've never once looked at someone and said "wow, I want to be with that person." But something has changed. I realize looking back before the flirting, that I had the smallest crush on him but I refused to acknowledge it. Now that we have been hanging out and sleeping together, I just want to be with him all the time. He is a pretty lowkey dude and I am using all of my self control to not come off as a clingy child. I'm kind of bad at reading social cues, especially when it comes to flirting and relationships. I can't tell if he actually likes me or if he just wants to sleep with me. I feel that he does like me because when we talk, 90% of the time it is non-sexual and about the things we like or daily stuff, like work. I've never experienced the feelings that I'm feeling right now which makes this even more confusing. The other night, I stayed over his house. We spent the whole night having sex and cuddling and I felt so happy and safe. I realize that it's not love and that I may just be feeling high from the dopamine in my brain but I truly don't know how to process these feelings or how to know if he wants to date. I know it's too early for the "what are we question" as it's only been about a month and a half since we started hanging out. I feel kind of stupid feeling this way too. I think it stems from my fear of relationships. It just seems silly to feel this worked up over a guy.

 

Anyway please go easy on me. I know I need to tell my friend. I'm just terrified. And I realize that I probably should not have slept with him so early on, but I wasn't expecting to catch feelings for him. When I told my friend I wasn't interested in sleeping with him, I truly meant it. But when the proposition was brought up it just felt right, and so far, I do not regret it.

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He's right, it's not your friends business. I'm not sure why you feel such a need to disclose such personal information to her. It's one thing to share crushes or if you had a bad day, etc, but it's no ones right, (not even a best friend) to hear about what you do sexually and with whom.

 

I'm also wondering why it is you think that it's okay to have a man take your virginity, but it's not okay to talk to him about your feelings or ask him where it might be going.

You don't need to be clingy about it , or demanding. But it does make sense to actually talk to him and be on the same page.

If you can't talk about sex with him or what it means, then perhaps that's a sign that you shouldn't be doing it, after all, it's your body and you have a right to know where you two are headed.

 

I know this is all new to you and you're unsure of yourself, but truly, you don't need to be sharing sexual secrets with your friend (even if it's her brother).

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Thank you for the response. I guess I feel the need to tell her because she brings it up all the time. She wants to know if its happening and I feel like keeping it a secret is lying. Also whenever we have girls night with our other friends, all they talk about is sex. I don't have an issue with it, but I feel like they're so open about it, they expect me to be too. I really wouldn't have an issue being open about it, if it wasn't for the fact that it's her brother.

 

When it comes to talking to him about my feelings, I guess I'm just afraid. I'm the type to bottle things up because I feel like I'm bothering people by opening up. Part of me is afraid he's going to laugh in my face about the idea of dating (though I know that won't happen). I want to talk to him and see if we're on the same page, but I don't know what to say or how to do it.

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I am guessing you're all still young. I only say that because women don't discuss sex like that, at least not typically.

 

It's somewhat odd that she keeps asking too. It really isn't her business.

 

Before you mention anything to him, do you want to date? Or are you okay with a casual relationship that is mainly sexual? Also, are you making sure that you're using protection of some kind?

 

If he is any kind of decent man, he won't laugh in your face. It should be okay to discuss what's going on between you. It's not weird or abnormal, most people who start a sexual relationship want to know where it's headed or what it means...that's perfectly normal.

 

Next time you're alone, I would start off by telling him that you enjoy spending time with him and was wondering if he was happy with things being casual or if he ever considered dating.

 

It's a reasonable question.

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I'm trying to get into the mindset of when I was your age. I know that friends can be nosey about what's going on between you and someone, especially if it's a brother.

Maybe she even finds it somewhat exciting because she knows and cares about both of you.

 

The thing is though, it will get awkward. If you tell her, she will press you for more details, and there's a good chance she will get upset if you don't tell her or don't continue to answer her questions. The brother will also feel annoyed that his sister now knows his business, as no doubt she will ask him about it too now or tease him, etc.

It really is opening a box you might not want open after all.

 

I mean, this is a personal situation between you and he, and it's also not right including the sister, you know? It will get all kinds of awkward and strange.

Granted she's your best friend, but this is also why dating a best friends brother, can get complicated.

 

For the time being, just tell her you don't want to discuss things, if she keeps pressing, then tell her outright that it's awkward for you to be seeing him and telling her and you hope she understands if you don't talk about what goes on in the bedroom.

 

If she's truly your friend and respects your friendship, she shouldn't get mad.

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I'm 21 and my friends are 23-25. They're a very rowdy bunch and I think they just find it funny to be vulgar and talk about these things in a ridiculous amount of detail. They don't find it weird or unusual. I think she's just a nosey person in general. If she wants to find something out, she will. I've watched her play detective hundreds of times, which is why I think I feel so nervous about my situation. If she's going to find out, I would want it to be from me then someone else. I don't want her to accuse me of sneaking around.

 

I am interested in dating, but I think I would still be interested in having a casual relationship if he declined dating. I don't know if that would be a good idea or not though. I think I would feel sad if I found out he was sleeping around, but I realize that's out of my control if we're not dating. And I don't believe he would laugh in my face. My anxiety is just telling me he would because he may not see anything in me aside from sex.

 

I'm trying to figure out when he wants to hang out again and then I think I'll try to bring it up if the timing feels right.

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Oh my, ...sneaking around? She sounds, erm...somewhat pushy. I don't like pushy people. Despite what she thinks, it's still not her business. I imagine that if she continues getting into people's business like this, someone, at some point, is going to set her straight as most people don't appreciate overbearing or nosey people.

 

Do you feel you relate to your friends in how they are? Do you think it's possible that maybe you and they aren't compatible in some areas?

 

Once again, with the situation concerning the brother. You could be getting yourself further into a situation where you might potentially get hurt.

Just say for instance that you do ask about dating, and he declines. So you agree to keep it casual. If you're starting to have feelings for him, it will get harder and harder to deny those feelings. And it's perfectly normal as well to become emotionally attached to him. Not only did he take your virginity, but you're both spending time together and sharing intimacy.

Tread carefully and protect your heart.

 

I would advise to ask when you feel the time is right, if he ever considered dating or if he prefers to keep things casual.

If he says he prefers to keep it casual, then it truly is up to you whether you're willing to risk your heart, or not.

Bring it up when you're ready and feel okay about it.

Try to be confident about it. I am certain you have a lot to offer someone in terms of dating, so don't sell yourself short.

Edited by SherrySher
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I realize that getting involved with my friends brother could potentially cause things to be awkward. I knew this going in to it and I still chose to do it. I'll just have to accept the consequences if they should arise. I also worry about how he would feel if she found out because he really doesn't seem to want her involved. But she has been persistently asking the both of us about it. The other day I went to their parents house for a BBQ and she was dropping little jokes and watched us whenever she left a room. We were trying so hard to not look suspicious because it was not the time nor the place for that conversation. She said that I'm just a child and that he shouldn't be acting creepy towards me. I always say that he's not being creepy. I think her main issue is the age difference. He is 7 years older than me, so I can understand the concern but at the same time, I'm not a child. By her making comments like that, all it does is make things feel awkward between the two of us(myself and him). I think she may be jealous that he's talking to me so much too. She said she's barely heard from him and that I'm a "brother stealer". She said it jokingly but I wonder if she really meant it as a joke. When I told him this, he just laughed it off and said she'll get over it. His response to her is that it is none of her business but I think that just makes her more curious. I don't understand why she is so obsessed either.

 

I think that when she brings it up again, I will try saying what you suggested. That I'm not interested in discussing these things with her. Really, thank you for the advice. I'm feeling a lot better now that I've been able to vent a little. This really has been stressful for me, even if it's not that big of a deal.

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There's really only one thing going on. Your first dating/sexual experience. If you want to have the exclusive talk, you should.

 

Make sure you see your doctor/ clinic for contraception and STD advice.

 

Not sure what your friend has to do with this. Even though your new BF is her brother, it may be best to employ some discretion.

 

Sooner or later the fact that you are dating will come out, unless you decide you just want hookups and want to keep that private.

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she has been persistently asking the both of us about it
she was dropping little jokes and watched us whenever she left a room

 

I'm just a child and that he shouldn't be acting creepy towards me
that I'm a "brother stealer"

 

None of that is okay.

 

She sounds immature to be honest and some of her comments are downright offensive. You're right, you're not a child, you're a grown woman by the age of 21. Even if he is 7 years older than you, you have a right to be with him or date him if you choose to. And no, he's not being a creep.

 

She's overstepping her place. I wouldn't cause a war over it, mind you. But I would tell her politely that you're not okay with her making jokes like that or pushing you to discuss things you're not comfortable discussing.

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She definitely can be pushy at times, but I still find her to be one of the best and most loyal friends that I have ever met. Maybe I have low standards because I have not always had the best people in my life but so far she has been the best despite her pushy and somewhat over dramatic personality. When it comes to if I can relate to my friends, I think that I do enjoy their company. I don't mind crude humor in the slightest. And my friend and I are very a like in our humor. I just never had much to contribute to when it came to personal stories for obvious reasons. But honestly, for the first time in years, I truly love my friends. I've always had a hard time making friends and my friend has introduced me to a lot of her other friend groups. For the first time in my whole life, I feel really happy with my social life. I don't know how she managed to find so many great people but I'm happy she decided to introduce me to them all.

 

I can understand what you're saying with him. I know that if he declines a relationship and I continue doing things in a causal manner that I'm most likely going to get hurt. I will definitely do my best to keep my heart and well being in mind. I know that at this point, all I can do is ask and see how he feels about the situation and go from there. The hard part is going to be getting the strength to ask him and not chicken out. I know in the grand scheme of things, this is so small, but it feels so big.

 

And thank you. I will try to be confident.

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I wasn't sure if I was just being dramatic, but her comments had been causing me some stress. I'm glad you mentioned this. Next time she makes a comment, I think that I'll politely discuss with her why they're inappropriate. Maybe I can get her to actually open up about what her problem is about it so we can move passed it. Obviously, she is having some sort of issue. I think all of the comments is what's making me feel pressured to tell her. Up until now, she has been a wonderful friend to me. It kind of hurts that she's been acting so strange which is why I'd like to understand what she's so upset about.

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Thanks for the advice, Wiseman2. I think that I will have the talk with him about if he's interested in dating. I just want to wait for the right time. I've been reading that if you do it too soon, it can "spook" people away. I'm not sure how true that is, but I still think I should feel it all out before jumping in with the question.

 

I plan to go to my dr soon to be sure that I am being safe. The last thing I want is an unplanned pregnancy or STD.

 

When it comes to my friend, I'm not sure if you read my replies to SherrySher, but I went into a bit more detail about what I'm experiencing with her. She's been very pushy to know details. At first I thought I just wanted to tell her because it was out of respect, but now I'm thinking that I just feel pressured to tell her.

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Don't try to fix "her issues". Lighten up. If you or her brother don't want to talk about it fine. However why would dating a friend's brother be such a secret and issue?

 

It sounds like she's teasing you about it and perhaps a bit too much. Why not just look at her when she insinuates (correctly) that you and her brother are dating and just say " so?".

 

This is partly your issue because you want to keep this some sort of big secret but for whatever reason.

 

People date siblings of friends all the time. The more you try to make this a big mystery, the weirder it will get.

Just lean into it with a "so what" ? mindset.

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I wasn't really looking to fix her issues, just understand why she's teasing so harshly. I didn't appreciate her calling me a child, especially in front of him and their parents. And honestly, I don't want it to be this big mystery or secret. I'm ok with being open about it. Her brother is the one who wants to keep it quiet. I don't want to overstep his boundary by saying more than he was comfortable with his sister knowing. I'm not interested in sharing every little detail with her like she may want, but if she knew it was happening, I don't think that would be a bad thing either. I will try to adopt more of a "so what" mindset, but I feel like that's just going to make her more curious and pushy.

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Why? Ok so how do you want to solve this problem if she is teasing you and HE wants You to be a secret?

 

Get away from the whole family if he wants to keep you a secret, but has clearly told her and she is "harshly teasing" you about it. Why sleep with or be friends with people you can't trust?

Her brother is the one who wants to keep it quiet
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"what are we?" you are in a friends with benefits situation. If the conversations went towards feelings/emotional connection and how much he misses you, how much he likes being with you and talk about a future together, and he was taking you out on dates, then that's leading to a relationship. You are friends having sex.....that's it. IMO if a man is serious, he tells you.

 

As for your friend, she's no dummy, she KNOWS, she just wants to see if you would ever tell her.

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It sounds like she's teasing you about it and perhaps a bit too much. Why not just look at her when she insinuates (correctly) that you and her brother are dating and just say " so?".

 

This is partly your issue because you want to keep this some sort of big secret but for whatever reason.

 

I don't think that's the problem here, Wiseman.

 

She's not even sure if they are dating. I know you've never been a younger woman, but it is a huge deal as to who takes your virginity. So for this man to have done that, and they are now still seeing each other and sleeping together, but not knowing how he truly feels..any everything still up in the air, that alone can be anxiety provoking.

 

Then you have a nosey sister pushing for answers, that she (OP) doesn't necessarily know and doesn't want to upset the brother by being all gossipy and giving out information..it's not an easy situation as you try to make it out to be.

 

You can't just "lighten up" about it. There's a lot of heavy feelings on the line. You're invalidating her feelings and how much is on the line by saying that.

 

The best friend has no right to be pushing things or to be forcing answers that quite frankly, are none of her business.

 

And until OP actually speaks to this man about what might be going on between them, it is a precarious situation where OP could be quite hurt. So it's not something to take lightly nor does she know if they are even going to date at the moment.

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