The Cookout

Stan Zero · 9/15/21

A friend of mine has this awesome sister I am very into. We all hang out sometimes, and I think she's hilarious, sexy and smart all rolled into one person. But.... she happens to be one of my best friends sisters. I haven't told my friend about this either, but I've considered asking her out on an official date, but I don't know how my friend would take it. Should I just be flat out honest and ask my friend if he has my blessing to ask her out? Or should I just ask her out without asking him? We're all adults, but still, I feel like I'm kinda stabbing him in the back if I don't at least let him know.

Idk, would you date a friend's sibling?

Jay · 9/15/21

Stan Zero said:
A friend of mine has this awesome sister I am very into. We all hang out sometimes, and I think she's hilarious, sexy and smart all rolled into one person. But.... she happens to be one of my best friends sisters. I haven't told my friend about this either, but I've considered asking her out on an official date, but I don't know how my friend would take it. Should I just be flat out honest and ask my friend if he has my blessing to ask her out? Or should I just ask her out without asking him? We're all adults, but still, I feel like I'm kinda stabbing him in the back if I don't at least let him know.

Idk, would you date a friend's sibling?

You need to figure out what you value more, your friendship with him or the prospects of dating her. If you value your friendship more then you need to talk to him and get his approval before you do anything. Do you think she even likes you? Has she given you any clear indications of interest? If it’s a shot in the dark it may not even be worth it.

Mastamind · 9/15/21

Bro depending on how cool you are with the dude it might not be worth it. You're risking losing two people instead of gaining. There's plenty of fish out there homie.

Lamont · 9/15/21

Mastamind said:
Bro depending on how cool you are with the dude it might not be worth it. You're risking losing two people instead of gaining. There's plenty of fish out there homie.

True statement. OP, you need to analyze the opportunity cost of making a move on your friend's sister. The upside is dating her, the downside is losing him, is it worth it? I can only speak for myself but the number of friends who I can trust and rely on continuously decreases while the number of women at my avail increases. It's a vast ocean, don't settle for the first fish that taps your hull.

Geoff · 9/15/21

You trying to marry her?

Rollie Forbes · 9/15/21

Mastamind said:
Bro depending on how cool you are with the dude it might not be worth it. You're risking losing two people instead of gaining. There's plenty of fish out there homie.

This.

Lamont · 9/15/21

Stan Zero said:
A friend of mine has this awesome sister I am very into. We all hang out sometimes, and I think she's hilarious, sexy and smart all rolled into one person. But.... she happens to be one of my best friends sisters. I haven't told my friend about this either, but I've considered asking her out on an official date, but I don't know how my friend would take it. Should I just be flat out honest and ask my friend if he has my blessing to ask her out? Or should I just ask her out without asking him? We're all adults, but still, I feel like I'm kinda stabbing him in the back if I don't at least let him know.

Idk, would you date a friend's sibling?

If it doesn't work out, you will always be ostracized. Things will never be the same once you dip your pen in her ink.

Stan Zero · 9/17/21

Jay said:
You need to figure out what you value more, your friendship with him or the prospects of dating her. If you value your friendship more then you need to talk to him and get his approval before you do anything. Do you think she even likes you? Has she given you any clear indications of interest? If it’s a shot in the dark it may not even be worth it.

Thanks. I really do value our friendship, we pretty much grew up together. I like his sister, but I think our friendship is more important. I don't even know if it'd work between us, and if it doesn't, I could see it making a ripple in our friendship, or possibly end it.

Mastamind said:
Bro depending on how cool you are with the dude it might not be worth it. You're risking losing two people instead of gaining. There's plenty of fish out there homie.

Yeah, that's one thing I don't want. I fear it a lot, because we have been friends forever now, and I'd rather not lose either of them as friends. But, she's just so cool and, ahhh idk what to do.

Lamont said:
True statement. OP, you need to analyze the opportunity cost of making a move on your friend's sister. The upside is dating her, the downside is losing him, is it worth it? I can only speak for myself but the number of friends who I can trust and rely on continuously decreases while the number of women at my avail increases. It's a vast ocean, don't settle for the first fish that taps your hull.

I see where you all are coming from. I really like his sister, but I don't think I'm going to make that move. If there is a chance that I risk losing two friendships, than I'd rather not risk it at all. His sister is awesome, and essentially my dream girl, but my friend has been there for me through thick and thin and we'd do anything for each other.

And yeah, true, more fish in the sea. I'll find someone. :) Thanks!

Lamont said:
If it doesn't work out, you will always be ostracized. Things will never be the same once you dip your pen in her ink.

Yeah, I don't think I'll risk it. Mainly because I know that there is that possibility things won't work out, and I don't want any bad blood between them.

Thanks guys, for kinda talking me off this ledge of stupidity haha! I was about to make a big mistake me thinks.

Sovereign · 9/17/21

Stan Zero said:
Thanks. I really do value our friendship, we pretty much grew up together. I like his sister, but I think our friendship is more important. I don't even know if it'd work between us, and if it doesn't, I could see it making a ripple in our friendship, or possibly end it.

Yeah, that's one thing I don't want. I fear it a lot, because we have been friends forever now, and I'd rather not lose either of them as friends. But, she's just so cool and, ahhh idk what to do.

I see where you all are coming from. I really like his sister, but I don't think I'm going to make that move. If there is a chance that I risk losing two friendships, than I'd rather not risk it at all. His sister is awesome, and essentially my dream girl, but my friend has been there for me through thick and thin and we'd do anything for each other.

And yeah, true, more fish in the sea. I'll find someone. :) Thanks!

Yeah, I don't think I'll risk it. Mainly because I know that there is that possibility things won't work out, and I don't want any bad blood between them.

Thanks guys, for kinda talking me off this ledge of stupidity haha! I was about to make a big mistake me thinks.

Good man. It ain't worth it joe!

sourgrapes · 9/17/21

This can get real messy real fast. I had a friend who dated her brother's close friend. What ended up happening is that she put a wedge between them, not intentionally but it happened. He ended up having to choose between my friend and his friend and he ended up choosing him but he is no longer welcomed at family events because of it. They took her side on everything and he has been shunned.

Lamont · 9/17/21

Stan Zero said:
Thanks. I really do value our friendship, we pretty much grew up together. I like his sister, but I think our friendship is more important. I don't even know if it'd work between us, and if it doesn't, I could see it making a ripple in our friendship, or possibly end it.

Yeah, that's one thing I don't want. I fear it a lot, because we have been friends forever now, and I'd rather not lose either of them as friends. But, she's just so cool and, ahhh idk what to do.

I see where you all are coming from. I really like his sister, but I don't think I'm going to make that move. If there is a chance that I risk losing two friendships, than I'd rather not risk it at all. His sister is awesome, and essentially my dream girl, but my friend has been there for me through thick and thin and we'd do anything for each other.

And yeah, true, more fish in the sea. I'll find someone. :) Thanks!

Yeah, I don't think I'll risk it. Mainly because I know that there is that possibility things won't work out, and I don't want any bad blood between them.

Thanks guys, for kinda talking me off this ledge of stupidity haha! I was about to make a big mistake me thinks.

I'm glad you stopped thinking with your penis.

lexodyssey · 9/18/21

sourgrapes said:
This can get real messy real fast. I had a friend who dated her brother's close friend. What ended up happening is that she put a wedge between them, not intentionally but it happened. He ended up having to choose between my friend and his friend and he ended up choosing him but he is no longer welcomed at family events because of it. They took her side on everything and he has been shunned.

I've seen this happen before. It's a big gamble because I feel like the friend and family would always take her side so you either have to get married or lose a friend. There's no recovering the friendship if the relationship falls apart.

Red Velvet · 9/18/21

lexodyssey said:
I've seen this happen before. It's a big gamble because I feel like the friend and family would always take her side so you either have to get married or lose a friend. There's no recovering the friendship if the relationship falls apart.

Facts. When I dated my brother's friend, it was over for their friendship.

Jay · 9/20/21

lexodyssey said:
I've seen this happen before. It's a big gamble because I feel like the friend and family would always take her side so you either have to get married or lose a friend. There's no recovering the friendship if the relationship falls apart.

Happened to me, a lot of good friends I lost by dating a family member.

Tati 304 · 9/20/21

Stan Zero said:
A friend of mine has this awesome sister I am very into. We all hang out sometimes, and I think she's hilarious, sexy and smart all rolled into one person. But.... she happens to be one of my best friends sisters. I haven't told my friend about this either, but I've considered asking her out on an official date, but I don't know how my friend would take it. Should I just be flat out honest and ask my friend if he has my blessing to ask her out? Or should I just ask her out without asking him? We're all adults, but still, I feel like I'm kinda stabbing him in the back if I don't at least let him know.

Idk, would you date a friend's sibling?

Have you and the sister ever flirted?

Stan Zero · 9/21/21

sourgrapes said:
This can get real messy real fast. I had a friend who dated her brother's close friend. What ended up happening is that she put a wedge between them, not intentionally but it happened. He ended up having to choose between my friend and his friend and he ended up choosing him but he is no longer welcomed at family events because of it. They took her side on everything and he has been shunned.

Yeah, if there is a risk of losing either of them as friends, it's probably not worth it.

Red Velvet said:
Facts. When I dated my brother's friend, it was over for their friendship.

Sorry to hear that.

Tati 304 said:
Have you and the sister ever flirted?

I'd say yeah, we were kinda flirty towards one another at times. I think she liked me as well. My friend wasn't all too pleased about it haha! But nothing has come of it. Because I think she has held off on asking me out because of her brother, and I have held off because of my friendship with him. I've predicted things in my head countless times about what could happen if we did date.

Deleted member 1946 · 3/5/23

It depends on who the friend was and who the sister was.

MR-D-ROB · 3/5/23

You know them best. So do you think it would be cool? If things go south are you going to lose a friend?
I'd suggest talking to them both before you make a decision! Talk to your friend first.
Chances are if he's okay with it he can give you some tips on how to approach her to increase your odds of her saying yes!

Deleted member 1946 · 3/5/23

Stan Zero said:
A friend of mine has this awesome sister I am very into. We all hang out sometimes, and I think she's hilarious, sexy and smart all rolled into one person. But.... she happens to be one of my best friends sisters. I haven't told my friend about this either, but I've considered asking her out on an official date, but I don't know how my friend would take it. Should I just be flat out honest and ask my friend if he has my blessing to ask her out? Or should I just ask her out without asking him? We're all adults, but still, I feel like I'm kinda stabbing him in the back if I don't at least let him know.

Idk, would you date a friend's sibling?

I would mention it to him to see where the friend's mind is at.

Deleted member 1946 · 3/6/23

Jay said:
You need to figure out what you value more, your friendship with him or the prospects of dating her. If you value your friendship more then you need to talk to him and get his approval before you do anything. Do you think she even likes you? Has she given you any clear indications of interest? If it’s a shot in the dark it may not even be worth it.

Great response

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