Would you ever date your best friends sister?

[Anonymous]

What are your thoughts on dating your best friend’s sister? Would you ever give it a shot or would it cause too much problems? What would be the upsides and downsides to you?

[ScottStevens]

Did that once in College. We really had a great time together and my friend kinda like watching us go out on dates. That bad news is once the relationship went south, so did the friendship.

When you date a sibling of a friend, unless you are turning that corner where you are old enough to make it a marriage situation, you are going to run into the ending of a relationship, at that point your friend is now going to have to choose which side they are on. My suggestion would be to avoid putting your friend in that situation.

[Majeston]

I don't have a sister, but observationally, it seems hard to predict how a guy will feel about his sister's relationships (especially if she's younger). A lot of it is about their relationship. Some don't care, some get bizarrely jealous. I would probably be super cautious.

That being said, if circumstances were right and she came onto me, the uniqueness of the situation would likely be too much to resist.

On a sidenote, I pity dudes that have hot sisters. Because the rest of us are obligated as guys never to let them hear the end of it. A sister's hotness often becomes an in-joke with a friend circle

[dustybiker]

I liked one of my best friends (male) more than his brother, but he was taken by a lovely person so I was happy for them. If the opposite had been true I would have just asked him how he was about it first. Might even help break ice and guaranteed protection against too much hurt with a friend watching out for you. - If they know you are open about it, first, you get trust and healthier chance at happiness.

[Anonymous]

I am into guys and i would date her brother for sure lmao

[Vivaldi]

But you would not date me, even though you are straight.

[Opinion Owner]

I would :)

[ChrisMaster69]

I did, we had to hide it for over a year.

one of the worst moment was she was in my room and he was outside the door giving me encouragement but not knowing it was his sister.

I really felt guilty hiding it from him, however he was far too possessive and jealous of her (zero double standards here lol 🙄).

I also had a friend date my sister, and it’s just like la la la la I don’t want to know.

[Fireguy17]

I have, and it was my friend that set it up.
We had a lot of fun, but we had different goals at that point of our lives, so we moved on.
Still stayed friends.
As long as my friend would be ok with it sure, but I would always ask or let them know first.

[exitseven]

My best friend had sisters who were a year older than us. They were identical twins. I had the biggest crush on one of them and the other I would not look twice at. I would have definitely dated her if I had the chance. I would have treated her right too.

[Jamie05rhs]

There have been at least 3 specific situations in my life where I specifically recall declining to go after my friend's sister because it would have caused an awkward situation.

Which is ironic, because he probably knows that I'm the type of guy that would treat her well and he would probably be thrilled for me to date her.

[dustybiker]

Sounds like it’s her loss.

[Jamie05rhs]

@dustybiker Thank you. It is very kind of you to say that!
It was actually probably my loss, though.

[dustybiker]

Yes, harder for you.

[Jamie05rhs]

Thanks

[AngelMegumin]

If I feel genuine love towards her, yes. You can work out everything with your best friend and they can help you figure her tastes and habits.

[Twalli]

I probably would, although all of my friends had mich younger sisters if they had any at all. Ny sister's friends are a different story. Being 18 months older than my sister means that most of her friends are a bit younger than me. Some are pretty hot. If any were interested in me, I would probably agree to date them regardless of their relationship with my sister.

[Vikkrram]

For me i would never date my friend sister... i would not even look at her, even she is so beautiful... coz for me my friendship is important and i don't wanna mess up things doing so. So for me i would never.

[bruc3L33]

The upside is they're your best friends sister but the down side is if you guys get into a lover quarrel your best friend might not be your best friend anymore. I would gauge the situation... I mean... Is it truly love... Would you do anything for her... Including leaving her alone?

[AviatorTom]

I have dated my best friends' sister when I was much younger. It didn't last though. He had no problem with it. In fact, he and his parents were hoping the relationship would last.

[slatyb]

Definitely. Why not? I already like my future brother-in-law. I would expect him to be happy for both of us.

[chickenchips27]

Once thought about it but no. She's not my type. Honest answer. No troll.

[lovesummerA7]

But…. a warm snug pussy…. is just that…. I wouldn’t turn that down…. shooting load after load SO DEEP

[DeltaCharlieEcho]

Nah, I've always been incorporated into my best friends' families as part of theirs so dating one of their sisters would be like dating my own sister. Couldn't do that.

[Relux47]

Before I graduated from high school I probably would’ve if I knew they had a sister and if she was interested/also around my age. After high school nope

[IncognitoBandito]

Best friend's sister sex is VERY tempting, especially if she is hot and older.

[Pj1981]

Yes. They would get over it cause I'm such a classy guy lol

[Lostveryloost]

Sure more if she was sweet and hot I wouldn't care what anyone though

[Dinosaursandanime65]

Probably not, that’s be a wee weird. Like when you have a head on your chest

[Slim57]

I tried and they tried to hook us up but they were never interested back lol

[lovesummerA7]

That’s depends….. If she’s homlier then a milk bucket no…. but a side gal to fuck anytime - Yes

[Vivaldi]

Do you fuck gals?

[Elliegirl]

I married my best friend’s brother!