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Finding a great guy to date nowadays seems impossible for some women, so when she finds what seems like the perfect guy, she should go for it, right? What to do?! A girlfriend of mine found herself in this predicament. She had known him for years and he was a great friend of the family. They flirted here and there, but her brother just chalked it up to his younger sister having a little girl crush on one of his friends - until she came of age. Maybe I was just oblivious. But I would imagine that if I thought very highly of both my brother and my best friend, why would I have an issue with them dating?

The problem is I knew too much. You know all those gross and embarrassing habits you have that you hold back on in a new relationship?

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And how you hope that by the time they come out, they love you enough already? Yeah, I had already heard all about his. Like, it's hard to have a romantic attraction to someone when you've spent years hearing stories like that time he clogged the toilet really bad No fucks given but I cannot imagine anyone I was friends with being attracted to my sister because she's crazy.

Personally I have nothing against it.

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However, in the movie she had HUGE reservations about her friend dating her brother, and so I thought it was kind of shitty for her to pursue it and kind of broke the trust between friends, I guess? IRL I have nothing against it but if my best friend hated her brother, I probably wouldn't pursue him.

We all hung out quite a bit. She took the break up well and things were amicable until she started dating a conservative white dude that really talked down in the fact that we would all hang out. So she stopped hanging out, and me and her sister have grown to have a pretty strong friendship.

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It's been a while, but at this point the girl I dated is pissed I have a relationship atall with her sister. I wouldn't.

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I tend to see my best friend's family as almost like extended family to me anyway. I wouldn't like my friend to date my sibling but I wouldn't stop it either.

Sep 10,   My best friend just started dating a wonderful guy. They have a great rapport, have been spending a lot of time together, and the best part is, I already know him incredibly well he's my brother. This is also the problem. My friend doesn't have the best track record with men. And though things seem to be going great right now, I can't Author: Julie Klam. Long story short, I left Germany early due to my depression over my host brother, and it's continuing here at home because of these dreams, and I miss him so much. My dad also died last year on my birthday, so that made it REALLY hard for me to handle all of this. Please, if you think you can help me, I would love to hear what you have to say. That's a tough one. Brothers can be VERY competitive. If you had asked if you should consider dating your ex's brother, I would likely have advised against it. You have now inserted yourself into the very heart of all the stuff that exists betw.

My best friend doesn't allow me to date his brother. Who would be perfect for me, but oh well. He mainly wants me to stop talking about how hot his brother is which I always do when I want to wind him up.

I was thinking the same thing when I read her response, but then hearing someone talk about how hot your brother is can be annoying in general. And if my sibling dated my best friend, I'd be concerned for my best friend, because he'd be the one to end up getting hurt.

My sister would be fine. They're both good people, but she wouldn't be good for him.

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In theory, yes. My best friends don't have siblings that I'm attracted to. But I'm okay with the concept. We're all mature enough that we could handle it if there was a break up. If my sister were available, I wouldn't, in theory, have a problem with her being involved with a best friend of mine. But I'd be concerned because my friends tend not be her type at all. It would be an odd match. I'd feel awkward dating a friend's sibling and I'd just plain feel bad for my friend if they ever dated my sibling.

I briefly dated my younger brothers friend The guy was really nice and we are still friends today but my brother just dealt with too much shit-talking from his friends ppl making sexual jokes and shit I probably would but I would really make sure that we would be a match before getting super serious just because if the relationship doesn't work out, I wouldn't want to be out two relationships.

Sibling dating best friend would probably take some adjustment but ultimately I'd be fine with it as long as they are both happy with each other. The first fight though would be tough to deal with though! My brother married one of my close friends. My brother and I are very close, so I was thrilled when they began dating.

I essentially vetted her through years of friendship, so I knew she was a good person worthy of someone as wonderful as my big brother. They've been married for about 6 years. We just skip the "in law" part and call each other sister. My brother and I are vastly different people.

As much as I get along with his girlfriend, I wouldn't call us close. I don't have a bestie, but one of my closest friends [my age] almost dated my older Brother [4 yrs older].

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He was 'eh' about it and my friend was keen. But they both had the decency to ask me how I felt. I felt weird. I honestly didn't think she was good enough for him, character wise, and I also knew she was looking for something more casual and self-validating. My brother was starting to get serious about his partners. Also, how awkward it would've been having her visit, knowing they're having sex in the next room?

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It's common for children to stay with parents until married. And would I have to acknowledge her every time? Would I have to entertain her when my brother was busy? So many possibilities, none were favourable. I would, and I'd be fine with my sibling dating my best friends.

I have a policy of not policing who someone falls in love with. It's not a big deal, imo, unless you make it one. I'm also fine with my friends dating my exes, provided those exes are good people.

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And so on. I respected my friend more and didn't want to deter my relationship with her or make it more complex. I'm happy I did this, he found the real love of his life later on and I've never seen someone more happy in my life.


Sure, I don't see why not, as long as they're decent people. Assuming there's no large age gap, of course. A few years ago I would have.

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But then time went by, she got some manky tatts, died her hair gross, dressed like a twelvie I have no interest in her anymore. It would be weird. Like really weird.

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For one, my brother is younger than me and my best friend and my best friend has always been pretty "big sister" to him as well. So I would definitely have a hard time adjusting to that. Plus I know both people very, very well and I don't think their personalities would mesh well if they were to date.

Jan 18,   Megara Jackson is Matthew Jackson's little sister, she's just one year younger than him. The two were orphans and had been for about 11 years. But since I was about 13, when I met them, I had a crush on her. The problem was that Matt was my best friend and he was not prepared to let me date. My one brother told the guy he should take me out sometime to I guess get me back into the dating world but my other brother seems to have a problem with it. I understand why it would bother him but I can't seem to get this guy out of my head. I would never want to screw up my brothers friendship and I have thought of the consequences if we. Jan 04,   One thing my girls and I did growing up was talk about the boys we liked, dated, kissed, hated, and then kicked to the curb. But imagining my girlfriend talking to me about kissing, getting.

And I'd have to come to terms with the fact that my best friend who has done all kinds of crazy things, often with me and who's sex life I know in detail is dating my little brother. I'd rather that not happen.

It would be way too weird. Luckily both are in happy relationships with other people so I don't think I need to worry. Growing up me and the bff thought it would be fun for our siblings to get married so we could be like "real sisters" though? I've never been interested in a friend's sibling but in theory sure, so long as my friend was okay with it. Maybe still if my friend wasn't ok with it because why would they not be?

My sister had a crush on one my best friends for a little while, I would have found it weird if they dated but I would have come to be fine with it if it was what they both wanted. I would never date my best friend's siblings. Or even regular friend's siblings.

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I think every long term girl friend one of my brothers has had was my best friend first lol. It doesn't bother me at this point. The girl he ended up having a kid with and they're still together is one of my closest friends. I have been dating my best friend's brother for over a year and a half now and we are finishing moving in with one another this weekend.

Her family set us up and it worked. He's amazing and we went into it knowing that it might be awkward.

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We also discussed in advance how, if at all, it would affect my relationships with my bestie and her husband and family if we split.

Same discussion was had with the bestie. I wouldn't want my siblings to date my friends just because they're very different from my friends. However if it made both parties happy then I'd stand back and let them try.

After all so far it has worked for me and the boyfriend pretty well. I have dated the sibling of one of my best friends. Turns out he was a huge jerk and so was she loooots of mental problems they didn't seem to really, truly be trying to fix. She never found out because it was a super short-lived fling and not an actual relationship like I had hoped it would be, and she also had mental issues - although I didn't know her brother did, too.

I terminated contact with her about a year or so ago, so I only have male friends. My brother told me he's straight.

He hasn't had any romantic or sexual relationships to my knowledge. If I did have a female friend and he was dating her, I would feel very uncomfortable about it and wonder why either of them had agreed to a relationship with the other. I dated one of my sisters friends for a bit, he was younger and more immature than me and that ended up ending our relationship. Add Opinion.

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Well, at least you understand the reasons it could be a problem. The biggest would be messing up your brothers' friendship with this guy. The other would be having to run in to him and hear about him if things do not work out. I am not a big fan of a girl asking a guy out.

He should ask you out.

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Maybe the one brother could feel that out with the guy and see if he is interested. And honestly, most guys don't know right up front how they feel about you. They do know if they have a physical attraction to you, but as far as whether they are ready for a relationship, that takes time and dating.

Ladies, the guy you are dating needs to be man enough to have that talk with your brother, and yes, as the sister, you too can do your bit by talking to your brother. And if your date is your sister's friend, try and talk to her about it and how you like the 'friend' and would like to ask her out on a Debolina Raja. Jan 02,   He is my brother, four years my senior. He doesn't look like me, which probably helps. He has his own interests and his own friends and is incredibly successful at what he does. While I won't say the precise industry, his job is important and well-respected and well-compensated. While I struggle at my third consecutive internship, he is. My brother married one of my close friends. My brother and I are very close, so I was thrilled when they began dating. I essentially vetted her through years of friendship, so I knew she was a good person worthy of someone as wonderful as my big brother. They've been married for about 6 years.

It may be too much pressure for him to try and date a friend's sister because, well, what if you have sex and then he decides that is as far as he wants to go. Maybe the one brother knows things about his friend that makes him feel this guy is not the best for you, who knows. Give it a shot. What I would do is talk to the brother that seems to have a problem with it. Maybe if you pull him aside and tell him how much you really like him, he might respect that and be okay with it.

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