Guys, Would you date your best friend's sister?

Question

When I was in college, I dated my best friend's sister. It didn't work out long term but we did date for almost 2 years. Her parents approved, thinking I might marry her. My best friend was neutral. Guys... Would you date your best friend's sister? Please vote in the poll.

Cormac995 · Accepted Answer

I would definitely date my best friend's sister "IF" me and him had a discussion about it and he gave me the ok. Bros before hoes. My best friend though in my opinion is actually great relationship material being honest I wish he was my sisters boyfriend because her current boyfriend is a douche and my best friend is a sensible stand up guy. He'd probably be good for her and might get her out of the brain rot gutter she's stuck in.

Finchie40 · Accepted Answer

Yes, I have before years ago. and my friend was cool about it , I just was honest with him and told him I hit it off with his sister and he actually laughed and shook his head and he said just treat her good but I know you will. Little did I realize , she just wanted to be FWB’s , which I was cool with considering I knew her for quite sometime before we started hooking up. I am still friends’ with both of them still

Chazmatazz269 · Answer

My best friend’s sister was far too young, and kind of a spoiled brat.
I did try to date other friends’ sisters, but neither went as planned.
Generally, i think family should be much more involved in each other’s love lives. Contrary to western propaganda, arranged marriages were generally very successful and still are. Our family knows things about us that sometimes we don’t understand ourselves, or we are unwilling to accept. Sometimes those are dealbreaker issues. Other times our family members might know things about someone we’re hot and bothered for, but we can’t see it through our rose colored glasses. For those reasons, people should be much more open to the approval and disapproval of their families concerning potential mates.

OlderAndWiser · Answer

1. I am married so I don't date anyone. 2. My best friend does not have a sister.

ProbablyClueless · Answer

I'd prefer not to, but dating is such a shit show. It feels impossible to meet people who aren't total lunatics, sometimes.

I have a friend who is considerably older than I am, who I've gotten the vibe that he might be trying to set me up with his daughter. He's in his mid 70s and I'm in my early 30s. His daughter is like 19 or 20.

The only reason I say that is because he'll make comments that make it seem like he's trying to point stuff out to me about her. Like she had a coming of age ceremony recently and he was showing me her dress. There was another video where she was making some kind of traditional food and he pointed out that she was wearing short shorts and stuff. I could be misreading that situation, but his wife has done similar things and it happens enough that it's... noticeable lol

Honestly, it's not like she's not a cool girl. She's a very impressive young lady. My only real gripe there is that she's my buddy's daughter. It feels more like my homie by extension than a prospective lover.

I first met her when she was 10 or 11 years old... kinda tough to see passed that.

EzraIsShy76028 · Answer

It's kind of strange but I'm not totally against it as long as me and her had a genuine connection.

I imagine my best friend would be furious though if I used their sister as just a one night stand or was abusive towards their sister, but I don't do shit like that anyway.

McLlovin · Answer

Thats an ideal situation. Not that I like any of my friends sisters lol. My sister is already married, but if my best friend was dating my sister I wouldn’t mind as long as he isn’t a player lol because then we have an issue lol, but i dont know why more people dont have the same view other than the friend is a player.

Anonymous · Answer

My best friend’s sister is one of the most amazing people I know

And I always chose to secure my friendship with him over taking a chance dating her

When i was younger I hated the circumstance that left me in

But now I have no regrets
We’re all a bit older and still friends
I doubt that would have been the case if I pushed for a date back in the day

StraightFaceAce · Answer

Neither of my best friends have sisters, so hard to say for sure, but if the romance is there I don't see why not.
I probably wouldn't just hook up with her though. That would be dumb; puts them in an awkward situation.

Purpleronnie · Answer

Nah that’s not for me. Just wouldn’t feel ok with that🤣… but one of ‘mine’ married my sister which massively changed our friendship but he was / is a decent bloke. Dont see either of them very much these days as they are hundreds of miles away.

Axel1969 · Answer

I didn't chose to but my best friends sister spent the night and wanted to to but I said no so she said let's wrestle and who ever wins gets to pick 🤔 Well I lost and I was all hers more than one time.

OneViewpoint · Answer

Sure. Why not? It could work out spectacularly. You’re a known quantity. She’s a known quantity. Her family already likes you.

ritxi · Answer

I have never been attracted to her, but if it happened it will depend on if she is interested on me. I don't know why, but many guys don't want friends to date her sister.

exitseven · Answer

My best friend had twin sisters. One of them I had the biggest crush on , i would not look twice at the other one. I would have dated her if I could have,

molonski2 · Answer

I would , the real difficulty is when you call it quits , I've also done it , we didn't last 2 years.

DrPepper12 · Answer

The word dated doesn't exactly convey the reality of our relationship. Fuck buddies would have been more appropriate if the term existed back then

zagor · Answer

Most of my friends' sisters I haven't even met, or very briefly. Now back in the day I had some friends with cute sisters but was kind of shy back then.

Sexiestjohnson · Answer

It ought to be the best approach but most friends frown at it

JHNS98 · Answer

I don't even know who my best friend is anymore...

LiamJHayden · Answer

No. My best friend, who is female, has been that since I was 4. She is like a sister, and so is her older sister.

Godihateyou · Answer

I had a crush on his little sister and he had a crush on mine. (They were both 2 years younger and in the same class) we never ever, ever would have. We are family now.

MJVillarama · Answer

That’s risky territory… but love’s got no rules

Xawyx-2 · Answer

Maybe but... none of my friends have a really hot sister.

UncTxn43 · Answer

Yes, I had a huge crush on my best friends sister. I would do anything for her. I was going to ask her out for dinner but she passed away. I regret not doing it sooner.

jJanSmit · Answer

I tried several years ago, but she turned me down.

Twalli · Answer

I would also date my sister's best friends. Not all of them, but a fair number were hot.

Sam2024 · Answer

Sure why not if she is my exact type I’m looking for. I don’t care what people think especially when it affects what I want.

MannMitAntworten · Answer

Nah, she’s too old now. :-p

Telekinetic-Potato · Answer

No, thit kids mother is nuts

Alex-Snow · Answer

Only if he was cool with me doing it

DavyJ · Answer

I did, albeit many years ago.

Fatal96 · Answer

No, plus they're older than me.

Guys, Would you date your best friend's sister?

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