Relationship with my best friends sister.

Wacker The Attacker

My best friend and I have known each other since primary school which is almost 25 years.

Recently I attended the world cup qualifying match between Sweden and Ireland in Stockholm. By coincidence, my friends sister was on the same flight to Stockholm. As a matter of courtesy I approached her to say hello and we had a brief conversation. The football match was on the friday so we arranged to meet up on saturday for a quick drink.

I didn't really know her that well and didn't expect anything to happen but we had a good time together in Sweden but nothing romantic or sexual took place there. However, we did arrange to meet up again on our return to Ireland. We've met several times since and things have started to blossom. We've been seeing each other and we broke the news to my friend about the start of our relationship.

Neither of us are married with no kids and there isn't a huge age gap between us. I'm 30 and she's 27. My problem is that he isn't particularly happy that we've started seeing each other.

I've tried discussing it with him but the conversation rarely goes anywhere. All I've managed to get from him is that he doesn't approve and that is kind of obvious.

On the one hand I don't want to lose his friendship but on the other hand neither I nor his sister are doing anything wrong by seeing each other.

How should this be broached?

I believe that he is the one with the difficulty and he is the one that needs to get over himself. I have absolutely no intention of stopping this relationship but don't want to cause any unnecessary strife either.

Whats the best way around it?

Unregistered.

Bros before hoes.

spitfireIRL

He needs to get over it. You're all adults

Meauldsegosha

You just have to give him some time to get use to the idea. Many years ago I dated my best friends brother and she hated the idea, didn't want to speak to us and thought our dating was wrong. Eventually she came around when she got use to us being a couple and seeing that we loved each other.

We broke up after a few years but that had nothing to do with my friend.

DeltaWhite

Unregistered. wrote: »

Bros before hoes.

^^^^ What age are you 15?

Do what makes you happy OP. Life really does go by too quick. His sister is not a little girl, she can make her own choices! Good luck OP!

ManOfMystery

He needs to get over it. You're 2 consenting adults, both single, no children involved, etc, etc .............. you're doing absolutely nothing wrong.

Here's a different way for him to look at it. His sister could have struck up a relationship with absolutely anyone, and he would know nothing about that person - they could be a nice guy, but could also be a drug addict or a criminal or a cheat, or whatever. In some ways, he should be happy that she's with someone who he obviously rates highly enough to be friends with for 25+ years.

Wacker The Attacker

ManOfMystery wrote: »

He needs to get over it. You're 2 consenting adults, both single, no children involved, etc, etc .............. you're doing absolutely nothing wrong.

Here's a different way for him to look at it. His sister could have struck up a relationship with absolutely anyone, and he would know nothing about that person - they could be a nice guy, but could also be a drug addict or a criminal or a cheat, or whatever. In some ways, he should be happy that she's with someone who he obviously rates highly enough to be friends with for 25+ years.

Thats a good way of looking at it. I'd never thought of it like that before.

Wacker The Attacker

DeltaWhite wrote: »

^^^^ What age are you 15?

Do what makes you happy OP. Life really does go by too quick. His sister is not a little girl, she can make her own choices! Good luck OP!

Thanks. I'm sure he'll come around in his own time.

ManOfMystery

Wacker The Attacker wrote: »

Thats a good way of looking at it. I'd never thought of it like that before.

I went out with one of my friend's exes many years ago. They were still friends. We (me and her) deliberated for a long time beforehand about whether to progress things further, worried about how he would feel.

I decided to sit him down for a chat one night and told him that we'd become close, wanted to go out, but would prefer it to have his blessing and knowledge beforehand. He was a bit surprised at the whole scenario but once he got his head round it, he remarked that he was glad she was going out with me (a longtime friend) than some randomer who may treat her badly.

When I read your post above I immediately thought back to my situation, which was similar.

SunnyDub1

same thing happened to two of my Friends, except he was 24 and his sister was 19.
Friend was seeing his sister for ages behind his back, it got out and he wasn't impressed.

8 years later and they are getting married this summer - the brother/Friend is best man

Taltos

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Taltos

Wacker The Attacker

SunnyDub1 wrote: »

same thing happened to two of my Friends, except he was 24 and his sister was 19.
Friend was seeing his sister for ages behind his back, it got out and he wasn't impressed.

8 years later and they are getting married this summer - the brother/Friend is best man

Brilliant. At least that makes me feel a whole lot better. We're a hell of a long way off anything even close to marriage but its nice to know these things can work.

Wacker The Attacker

ManOfMystery wrote: »

I went out with one of my friend's exes many years ago. They were still friends. We (me and her) deliberated for a long time beforehand about whether to progress things further, worried about how he would feel.

I decided to sit him down for a chat one night and told him that we'd become close, wanted to go out, but would prefer it to have his blessing and knowledge beforehand. He was a bit surprised at the whole scenario but once he got his head round it, he remarked that he was glad she was going out with me (a longtime friend) than some randomer who may treat her badly.

When I read your post above I immediately thought back to my situation, which was similar.

I think that might be the case here. He probably just needs to get his head around it.

mathproblem

I would refer you to the Ross-Chandler-Monica triangle from friends 'cos it rings very true for me: "my sister and my best friend!"(furious- whilst he's thinking it's a sordid affair).."my sister and my best friend"(fawning - once he realises the relationship has substance)

Just be a good guy with his sister and he will eventually get over it, the initial shock will probably just take time to get over for him but don't blame him for feeling it because he does have a lot to lose here & totally outside of his own choosing.

Merkin

Wacker The Attacker wrote: »

How should this be broached

He knows so it has been broached already and he doesn't need to be told again or have it reinforced. Trying to talk him around will just antagonize him so I would personally leave it and let him get used to the idea. Carry on as normal your friendship with him and treat his sister with respect/don't screw her around. If he sees that you make her happy and are treating her well then he will eventually accept it. Just give him a bit of time and it will be fine.

Unregistered.

Unregistered. wrote: »

Bros before hoes.

OP, friendships are just as important as relationships. Your friend's feelings of unhappiness about this situation are not unusual. You have to accept that you choosing to enter a relationship with his sister could potentially end your friendship with him, or even make it extremely uncomfortable for a long time.

You have got to ask yourself is it worth it? If you were not unhappy without her for the last 25 years, then surely you could continue to be happy without her, or with someone else and still maintain your friendship with him. I'd leave her if I were you OP.

judgefudge

Unregistered. wrote: »

OP, friendships are just as important as relationships. Your friend's feelings of unhappiness about this situation are not unusual. You have to accept that you choosing to enter a relationship with his sister could potentially end your friendship with him, or even make it extremely uncomfortable for a long time.

You have got to ask yourself is it worth it? If you were not unhappy without her for the last 25 years, then surely you could continue to be happy without her, or with someone else and still maintain your friendship with him. I'd leave her if I were you OP.

To a certain extent I would agree with this. I went out with my brothers best friend a few years back for a few years and it essentially ruined their friendship. I feel bad about it sometimes but it was down to my brother. For some reason he just couldn't or wouldn't accept it.

It depends on whether you think your mate will get past this? And if he doesn't, which is more important, an old mate or a new relationship?

It's important to bear in mind that, although I don't agree with your mates feelings on it, he may not change his mind. This could ruin your friendship, especially if the new relationship doesn't go well or ends badly.

I'm not saying don't go for it with the sister, but be prepared to lose your friend. He may not come around to your thinking! I hope he does though

ShaShaBear

Maybe a bit biased here, but my OH is going through this.

His best friend from primary school (they're 28, so about 25 years of knowing each other) has started seeing his 21 year old sister. Mind you, he has two kids and ongoing court battles with his ex. My OH made it very clear to his sister that he did not approve, simply on the grounds that after 25 years, he knows exactly what his best friend is like, in a way that she might never discover. He also mentioned that he finds it very tasteless mostly due to the age gap, as they started seeing each other when she was 20, and he had his first girlfriend when she was still in pull-up pants.

But my OHs main concern in this regard is that, although he loves his best friend to bits (or rather ex best friend, as this lad has suddenly ceased all contact with my OH as soon as the relationship got serious and he didn't need help getting in a good word) he knows exactly what way he is around women, sexually and emotionally, and the thought of both of these practises being placed on his sister is absolutely horrifying. At least with a stranger, he wouldn't know.

aN.Droid

I am a brother of 2 sisters one who is of age and to be honest I would not approve of my sister dating any of my close friends for the simple fact that if it went sour then I would be in the middle of it. Every little tiff I would be expected to take sides or to mediate. I know I would eventually end up cutting emotional ties with one side (most likely not my sister) if it did not end up happy in the end and that would be incredibly unfair on me as the brother.

Of Course I don't control them with strings so if something did happen then so be it but don't expect me to be happy about it. Take from that what you want OP

EireIceMan

See, i cant understand this. Im the eldest in my family with two younger sisters.
My best friend asked me one night over a pint could he ask my sister out.
I had no problem, in fact, was kinda hoping they'd get on. Despite him being a messer i knew he wouldnt mess her about out of respect for me and my family.
You're 'best friends', sit down and talk to him, he should be able to do that at least. If he has a problem, its his problem.
TBH, despite being messers, lads whatever i couldnt think of anyone better for my little sisters than my best friends.

ShaShaBear

EireIceMan wrote: »

See, i cant understand this. Im the eldest in my family with two younger sisters.
My best friend asked me one night over a pint could he ask my sister out.
I had no problem, in fact, was kinda hoping they'd get on. Despite him being a messer i knew he wouldnt mess her about out of respect for me and my family.
You're 'best friends', sit down and talk to him, he should be able to do that at least. If he has a problem, its his problem.
TBH, despite being messers, lads whatever i couldnt think of anyone better for my little sisters than my best friends.

But when you find out that your best friend has cheated on your sister, or your sister has decided she's not happy and dumps your best friend - what do you do then? I think the problem is that if you date your brother or sister's best friend, there will always be three in a relationship, and the person that gets hurt the most will always be the brother or sister that is forced to choose one side and lose another.

beks101

Wacker The Attacker wrote: »

I believe that he is the one with the difficulty and he is the one that needs to get over himself.

I find this a bit cold to be honest. You've been friends with this guy 25 years and all of a sudden you tell him you're in a relationship with his sister, just like that. No courtesy "would you be OK with me asking your sister out" or forewarning that you're thinking about her in that way. Surely you can appreciate how uncomfortable and weird that is for him? Do you have a sister?

He's got split loyalties to you and his sister and if the **** hits the fan in this relationship, he's stuck in the middle and likely to lose one of you (hint: likely not his sister). It won't even take a breakup - any old argument or tension between the two of you and he's piggy in the middle.

Not to mention the history ye have as mates - 25 years is a long time, Im sure you've seen each other get up to all sorts & his protective instincts towards his sister v his friendship with you are probably leaving him massively head fcuked.

I know you're probably infatuated with one another right now & that's watering down your sense of what issues he might have with it, but to gloss over his feelings on a technicality - "we didnt do anything wrong" - is a bit insensitive and might spell the beginning of the end for your friendship, if you're not prepared to see his point of view.

rainbowdash

ManOfMystery wrote: »

Here's a different way for him to look at it. His sister could have struck up a relationship with absolutely anyone, and he would know nothing about that person - they could be a nice guy, but could also be a drug addict or a criminal or a cheat, or whatever. In some ways, he should be happy that she's with someone who he obviously rates highly enough to be friends with for 25+ years.

On the other hand the best friend probably knows some of the OP's dirtiest secrets, which obviously he won't share here, but if the OP is an unemployed waster, drinks 7 nights a week, treats girls bad, has loads of debt etc. etc. then he might have a point.

On the other hand if the OP has a more normal profile then the friend is being a bit OTT.

username123

ShaShaBear wrote: »

But my OHs main concern in this regard is that, although he loves his best friend to bits (or rather ex best friend, as this lad has suddenly ceased all contact with my OH as soon as the relationship got serious and he didn't need help getting in a good word) he knows exactly what way he is around women, sexually and emotionally, and the thought of both of these practises being placed on his sister is absolutely horrifying. At least with a stranger, he wouldn't know.

I find the above weird. Why would you hang around with someone who you felt treated people so badly? I hang around with people who I like and respect. Id be delighted to see anyone go out with any of my friends because I believe my friends to be good people. I wouldnt be friends with someone who I thought treated the opposite sex in a "horrifying" way

Personally Id stay away from siblings of good friends simply because if it goes bad you are creating an awkward situation for your friend.

ShaShaBear

username123 wrote: »

I find the above weird. Why would you hang around with someone who you felt treated people so badly? I hang around with people who I like and respect. Id be delighted to see anyone go out with any of my friends because I believe my friends to be good people. I wouldnt be friends with someone who I thought treated the opposite sex in a "horrifying" way

Personally Id stay away from siblings of good friends simply because if it goes bad you are creating an awkward situation for your friend.

Something as simple as sexual preferences isn't really a reason to not be friends with someone, but it is a reason to make sure someone doesn't get anywhere near your sister. They might be simple faults in character to you as a friend, but they might be a different thing entirely when it's someone you are dating.

username123

ShaShaBear wrote: »

Something as simple as sexual preferences isn't really a reason to not be friends with someone, but it is a reason to make sure someone doesn't get anywhere near your sister. They might be simple faults in character to you as a friend, but they might be a different thing entirely when it's someone you are dating.

Certainly people are different in friendships than relationships. I may have misunderstood your original post, when you used the word "horrified" I thought it implied something more sinister than just sexual preferences - I thought you were implying a serious lack of respect with women. I dont really see why sexual preferences would make you not want someone to go near your sister though? Perhaps Im being obtuse, I just cant see why someone would mind what their sister enjoys in the sack? If thats all it is.

ShaShaBear

username123 wrote: »

Certainly people are different in friendships than relationships. I may have misunderstood your original post, when you used the word "horrified" I thought it implied something more sinister than just sexual preferences - I thought you were implying a serious lack of respect with women. I dont really see why sexual preferences would make you not want someone to go near your sister though? Perhaps Im being obtuse, I just cant see why someone would mind what their sister enjoys in the sack? If thats all it is.

I don't know, guess it depends. I know something sexual about a very close male friend of mine, and if he dare even thought about doing that thing to my sister, I'd kick him into next week! I know everyone looks on it differently, but I can agree with my OH in that it cannot be easy having heard your best friend's sex and "dumped the woman" stories, and now realising that any one of these stories could be repeated on his sister. Plus the obvious issue that if any one of these situations arose, and a row between the couple ensued, the best friend and sibling would come out the worst.

Your sister dumped me out of the blue, you have to convince her to take me back.
Your best friend is an absolute ay-hole and he tried to make me do X with him, you're never to have that creep near this house when I'm here again.
Your sister cheated on me man, if you had any respect for me as your friend you'd tell her to eff off.
Your best friend left me because he wasn't in love with me any more, how dare you speak to someone who broke my heart.
Your sister dumped me, I can't face her, so I'm going to refuse to attend all of your birthday parties, I wont come to visit at Christmas, I won't come down for a few drinks at the weekend, and I cant face sitting in your house to watch the footie.
Your best friend won't leave me alone since I broke up with him, he keeps sending me these really creepy texts and is harrassing me if he meets me out - I demand you stop him.

Just a few scenarios there, some of which have already occured in OH's case, and plenty of reason for BOTH sister and best friend not to be so selfish and think there can't possibly be anyone else they would be happy dating.

username123

^^^totally agree on those kinds of reasons. Ending up the man in the middle would be my issue.

EoghanIRL

Unregistered. wrote: »

Bros before hoes.

Lol, the lad code.

Taltos

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Taltos

The Corinthian

Unless you are very sure that the relationship will work, that she is 'The One', then it won't end well and you'll be doing a damage limitation exercise down the line.

Even if you are, your friend will no longer be your friend where it comes to you; if you have problems in the relationship in the future, if you need him to cover you on anything, his loyalties will be split and any help or advice he may offer will be caught between your interests and hers.

I'd avoid going down this road as I've seldom seen it end well.

statina

Have had a similar situation where I fell out with my friend over this. Avoid, avoid avoid if you value the friendship!

a posse ad esse

I will give another point of view. I have four older brothers and not once I'd consider dating any of their childhood friends and they never asked me out. I never looked at them as potential dating material. It had nothing to do with the fact that my brothers would disapprove (they would probably react the same as your friend, to be honest) or the strange dynamic or conflict that may come from it all. It was the sheer fact I considered my brothers' friends (their childhood ones) to be almost like an extension of my siblings. My brothers friends are kind, respectful, sound and some even good looking but I have or never had any romantic interest or attraction. I would be freaked out myself if any of them asked me out. It would literally feel like I was being asked out by one of my own brothers!

I don't know how close you are to your friend but if you are a childhood friend that came over to the house most of the time and hung around his family home it's almost as if you are his brother and that would feel strange, in my opinion.

December2012

How about simply staying out of it, like you would in any other relationship / dispute between two people you know?

Don't get involved and its not your problem.