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How to Deal With Asking Out A Friend's Sister
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up vote
1
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I've been friends with the oldest brother, Gary, since middle school. His younger brother Billy also integrated into our group of friends around high school and Billy, Gary, and I frequently played video games together online during this time. Near the later half of High School, Jennifer, the middle sibling became fully integrated into this group of friends. Then, Gary and I moved off to separate colleges and Gary's participation in the group has been reduced to about a 10th or less of what it used to be but I persisted. A year later, Jennifer leaves for college and comes to the one I am currently at. Lately we've been spending a lot of time together and I've been considering asking her out.
How can I best mitigate or deal with the potential issues, provided she accepts or declines?
Notes:
Billy, Gary, and Jennifer are intelligent and reasonable people
Jennifer had asked me to her prom and Gary asked me why I was taking his sister to prom with some hostility in a joking manner but was satisfied with my answer, which was I thought it would be a nice thing to do (which was true at the time, and I guess still is but would be overshadowed in the present)
Gary and Jennifer are very different people and don't get along perfectly, but are probably closer than most siblings.
This is in the United States
friends united-states relationships awkward-situations siblings
edited 42 mins ago
Tinkeringbell♦
20.2k1993122
asked 5 hours ago
netdenizen177
61
New contributor
netdenizen177 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
add a comment |Â
up vote
1
down vote
favorite
I've been friends with the oldest brother, Gary, since middle school. His younger brother Billy also integrated into our group of friends around high school and Billy, Gary, and I frequently played video games together online during this time. Near the later half of High School, Jennifer, the middle sibling became fully integrated into this group of friends. Then, Gary and I moved off to separate colleges and Gary's participation in the group has been reduced to about a 10th or less of what it used to be but I persisted. A year later, Jennifer leaves for college and comes to the one I am currently at. Lately we've been spending a lot of time together and I've been considering asking her out.
How can I best mitigate or deal with the potential issues, provided she accepts or declines?
Notes:
Billy, Gary, and Jennifer are intelligent and reasonable people
Jennifer had asked me to her prom and Gary asked me why I was taking his sister to prom with some hostility in a joking manner but was satisfied with my answer, which was I thought it would be a nice thing to do (which was true at the time, and I guess still is but would be overshadowed in the present)
Gary and Jennifer are very different people and don't get along perfectly, but are probably closer than most siblings.
This is in the United States
friends united-states relationships awkward-situations siblings
edited 42 mins ago
Tinkeringbell♦
20.2k1993122
asked 5 hours ago
netdenizen177
61
New contributor
netdenizen177 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
Is there a reason to think this is unethical in the US? She has already asked you out (prom) before, so it is not the first time you are out. What reason is then to consider that unethical? You should be more detailed about the problem you see.
– puck
4 hours ago
1
"Is this unethical?" Isn't really a question we can answer here. Ethics, despite popular opinion, tend to vary and generally fall into shades of grey rather than black and white, or good and bad.
– apaul
4 hours ago
Well the ethics question was a more tangential precursor to the main question, I suppose. Maybe I should have asked it in a more casual context. The prom thing seemed (but was not explicitly stated) as in a just-as-friends thing with a potential undertone. But my main thought is it kinda seems like an asshole move to go and date your friend's sister, but I've thought about the situation and figured Gary isn't Jennifer's keeper. However it still rubs me the wrong way and there might be an angle I'm not considering.
– netdenizen177
4 hours ago
Did you ever watch Harry Potter? He ended up dating and marrying his best friend younger sister. Nothing unusual.
– gnasher729
41 mins ago
add a comment |Â
up vote
1
down vote
favorite
up vote
1
down vote
favorite
I've been friends with the oldest brother, Gary, since middle school. His younger brother Billy also integrated into our group of friends around high school and Billy, Gary, and I frequently played video games together online during this time. Near the later half of High School, Jennifer, the middle sibling became fully integrated into this group of friends. Then, Gary and I moved off to separate colleges and Gary's participation in the group has been reduced to about a 10th or less of what it used to be but I persisted. A year later, Jennifer leaves for college and comes to the one I am currently at. Lately we've been spending a lot of time together and I've been considering asking her out.
How can I best mitigate or deal with the potential issues, provided she accepts or declines?
Notes:
Billy, Gary, and Jennifer are intelligent and reasonable people
Jennifer had asked me to her prom and Gary asked me why I was taking his sister to prom with some hostility in a joking manner but was satisfied with my answer, which was I thought it would be a nice thing to do (which was true at the time, and I guess still is but would be overshadowed in the present)
Gary and Jennifer are very different people and don't get along perfectly, but are probably closer than most siblings.
This is in the United States
friends united-states relationships awkward-situations siblings
edited 42 mins ago
Tinkeringbell♦
20.2k1993122
asked 5 hours ago
netdenizen177
61
New contributor
netdenizen177 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
I've been friends with the oldest brother, Gary, since middle school. His younger brother Billy also integrated into our group of friends around high school and Billy, Gary, and I frequently played video games together online during this time. Near the later half of High School, Jennifer, the middle sibling became fully integrated into this group of friends. Then, Gary and I moved off to separate colleges and Gary's participation in the group has been reduced to about a 10th or less of what it used to be but I persisted. A year later, Jennifer leaves for college and comes to the one I am currently at. Lately we've been spending a lot of time together and I've been considering asking her out.
How can I best mitigate or deal with the potential issues, provided she accepts or declines?
Notes:
Billy, Gary, and Jennifer are intelligent and reasonable people
Jennifer had asked me to her prom and Gary asked me why I was taking his sister to prom with some hostility in a joking manner but was satisfied with my answer, which was I thought it would be a nice thing to do (which was true at the time, and I guess still is but would be overshadowed in the present)
Gary and Jennifer are very different people and don't get along perfectly, but are probably closer than most siblings.
This is in the United States
friends united-states relationships awkward-situations siblings
friends united-states relationships awkward-situations siblings
edited 42 mins ago
Tinkeringbell♦
20.2k1993122
asked 5 hours ago
netdenizen177
61
New contributor
netdenizen177 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
edited 42 mins ago
Tinkeringbell♦
20.2k1993122
asked 5 hours ago
netdenizen177
61
New contributor
netdenizen177 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
edited 42 mins ago
Tinkeringbell♦
20.2k1993122
edited 42 mins ago
Tinkeringbell♦
20.2k1993122
edited 42 mins ago
Tinkeringbell♦
20.2k1993122
20.2k1993122
asked 5 hours ago
netdenizen177
61
New contributor
netdenizen177 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 5 hours ago
netdenizen177
61
asked 5 hours ago
netdenizen177
61
61
New contributor
netdenizen177 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
New contributor
netdenizen177 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
netdenizen177 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
Is there a reason to think this is unethical in the US? She has already asked you out (prom) before, so it is not the first time you are out. What reason is then to consider that unethical? You should be more detailed about the problem you see.
– puck
4 hours ago
1
"Is this unethical?" Isn't really a question we can answer here. Ethics, despite popular opinion, tend to vary and generally fall into shades of grey rather than black and white, or good and bad.
– apaul
4 hours ago
Well the ethics question was a more tangential precursor to the main question, I suppose. Maybe I should have asked it in a more casual context. The prom thing seemed (but was not explicitly stated) as in a just-as-friends thing with a potential undertone. But my main thought is it kinda seems like an asshole move to go and date your friend's sister, but I've thought about the situation and figured Gary isn't Jennifer's keeper. However it still rubs me the wrong way and there might be an angle I'm not considering.
– netdenizen177
4 hours ago
Did you ever watch Harry Potter? He ended up dating and marrying his best friend younger sister. Nothing unusual.
– gnasher729
41 mins ago
add a comment |Â
Is there a reason to think this is unethical in the US? She has already asked you out (prom) before, so it is not the first time you are out. What reason is then to consider that unethical? You should be more detailed about the problem you see.
– puck
4 hours ago
1
"Is this unethical?" Isn't really a question we can answer here. Ethics, despite popular opinion, tend to vary and generally fall into shades of grey rather than black and white, or good and bad.
– apaul
4 hours ago
Well the ethics question was a more tangential precursor to the main question, I suppose. Maybe I should have asked it in a more casual context. The prom thing seemed (but was not explicitly stated) as in a just-as-friends thing with a potential undertone. But my main thought is it kinda seems like an asshole move to go and date your friend's sister, but I've thought about the situation and figured Gary isn't Jennifer's keeper. However it still rubs me the wrong way and there might be an angle I'm not considering.
– netdenizen177
4 hours ago
Did you ever watch Harry Potter? He ended up dating and marrying his best friend younger sister. Nothing unusual.
– gnasher729
41 mins ago
Is there a reason to think this is unethical in the US? She has already asked you out (prom) before, so it is not the first time you are out. What reason is then to consider that unethical? You should be more detailed about the problem you see.
– puck
4 hours ago
Is there a reason to think this is unethical in the US? She has already asked you out (prom) before, so it is not the first time you are out. What reason is then to consider that unethical? You should be more detailed about the problem you see.
– puck
4 hours ago
1
1
"Is this unethical?" Isn't really a question we can answer here. Ethics, despite popular opinion, tend to vary and generally fall into shades of grey rather than black and white, or good and bad.
– apaul
4 hours ago
"Is this unethical?" Isn't really a question we can answer here. Ethics, despite popular opinion, tend to vary and generally fall into shades of grey rather than black and white, or good and bad.
– apaul
4 hours ago
Well the ethics question was a more tangential precursor to the main question, I suppose. Maybe I should have asked it in a more casual context. The prom thing seemed (but was not explicitly stated) as in a just-as-friends thing with a potential undertone. But my main thought is it kinda seems like an asshole move to go and date your friend's sister, but I've thought about the situation and figured Gary isn't Jennifer's keeper. However it still rubs me the wrong way and there might be an angle I'm not considering.
– netdenizen177
4 hours ago
Well the ethics question was a more tangential precursor to the main question, I suppose. Maybe I should have asked it in a more casual context. The prom thing seemed (but was not explicitly stated) as in a just-as-friends thing with a potential undertone. But my main thought is it kinda seems like an asshole move to go and date your friend's sister, but I've thought about the situation and figured Gary isn't Jennifer's keeper. However it still rubs me the wrong way and there might be an angle I'm not considering.
– netdenizen177
4 hours ago
Did you ever watch Harry Potter? He ended up dating and marrying his best friend younger sister. Nothing unusual.
– gnasher729
41 mins ago
Did you ever watch Harry Potter? He ended up dating and marrying his best friend younger sister. Nothing unusual.
– gnasher729
41 mins ago
add a comment |Â
1 Answer
1
active
oldest
votes
up vote
3
down vote
Well, sounds like you're interested in your friend's little sister and it also sounds like you're pretty set on pursuing a relationship.
So...
Let's take a moment to examine what sort of relationship you want to pursue with this young woman, cause if it was a young woman who meant something to me, that would be my first question. Are your intentions honourable? Do you intend to have some kind of respectful, lasting, and meaningful relationship, or is it just lust?
Admittedly I don't have a little sister, but I've had daughters, and if anything, that's probably a higher standard. You want the people who pursue the people you care about to treat them well. Any inclination that this pursuer's intentions aren't as pure as the driven snow, and all those nasty protective instincts kick in. You probably want to avoid those protective instincts. They may be bad for your friendships in the best case, and bad for your health in the worst.
Check your motives first. If you really want a real relationship with this woman, then proceed.
Next, think about your relationship with her brothers. Do they have a high opinion of you? Have they seen you behave questionably toward your previous partners? Effectively, would they think you're a respectable match for a young woman who means the world to them?
If you can check both of those boxes... Are you willing to risk all of these friendships for the relationship you might have with this woman? If that's even a question you have to think about, you probably shouldn't move forward. Because, doing this even in the very best circumstances, can and will, risk all of these friendships. Even if things go wonderful for years, if things turn bad, you should expect to have a falling out with all of these people.
Should you decide that your intentions are good, and that her brothers like and respect you well enough, and that it's worth the risks... Cause you will... Cause young love is like that... Brave, or foolish, or both... probably both. Talk to the young woman first. You're not asking her brothers for a date, you're asking her. She's your priority. If she likes you, and her brothers don't, they may get over it in time. If you ask her brothers first, she could and likely should feel somewhat demeaned and controlled.
(I realize that sounds counter intuitive given the opening paragraphs about the brothers respecting you, but bear with me.)
You'll be changing the context of all of these relationships. She'll need to see you as more than her friend, or her brothers' friend. And her brothers will need to see you as a potential brother-in-law. If you want this to go as smoothly as possible, and maintain those friendships, you'll need to seem like a good fit in both categories. But neither work if she doesn't like you, so that's going to be your first concern.
If she doesn't want to pursue something more with you, respecting that fully will be your best bet toward moving forward, without damaging all these friendships. (Another reason it'll be important to ask her before testing the waters with her brothers) Asking her brothers and then being shot down be her will likely lead them to question any and all interaction you have with her from then on.
answered 4 hours ago
apaul
45.2k23153222
add a comment |Â
1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
up vote
3
down vote
Well, sounds like you're interested in your friend's little sister and it also sounds like you're pretty set on pursuing a relationship.
So...
Let's take a moment to examine what sort of relationship you want to pursue with this young woman, cause if it was a young woman who meant something to me, that would be my first question. Are your intentions honourable? Do you intend to have some kind of respectful, lasting, and meaningful relationship, or is it just lust?
Admittedly I don't have a little sister, but I've had daughters, and if anything, that's probably a higher standard. You want the people who pursue the people you care about to treat them well. Any inclination that this pursuer's intentions aren't as pure as the driven snow, and all those nasty protective instincts kick in. You probably want to avoid those protective instincts. They may be bad for your friendships in the best case, and bad for your health in the worst.
Check your motives first. If you really want a real relationship with this woman, then proceed.
Next, think about your relationship with her brothers. Do they have a high opinion of you? Have they seen you behave questionably toward your previous partners? Effectively, would they think you're a respectable match for a young woman who means the world to them?
If you can check both of those boxes... Are you willing to risk all of these friendships for the relationship you might have with this woman? If that's even a question you have to think about, you probably shouldn't move forward. Because, doing this even in the very best circumstances, can and will, risk all of these friendships. Even if things go wonderful for years, if things turn bad, you should expect to have a falling out with all of these people.
Should you decide that your intentions are good, and that her brothers like and respect you well enough, and that it's worth the risks... Cause you will... Cause young love is like that... Brave, or foolish, or both... probably both. Talk to the young woman first. You're not asking her brothers for a date, you're asking her. She's your priority. If she likes you, and her brothers don't, they may get over it in time. If you ask her brothers first, she could and likely should feel somewhat demeaned and controlled.
(I realize that sounds counter intuitive given the opening paragraphs about the brothers respecting you, but bear with me.)
You'll be changing the context of all of these relationships. She'll need to see you as more than her friend, or her brothers' friend. And her brothers will need to see you as a potential brother-in-law. If you want this to go as smoothly as possible, and maintain those friendships, you'll need to seem like a good fit in both categories. But neither work if she doesn't like you, so that's going to be your first concern.
If she doesn't want to pursue something more with you, respecting that fully will be your best bet toward moving forward, without damaging all these friendships. (Another reason it'll be important to ask her before testing the waters with her brothers) Asking her brothers and then being shot down be her will likely lead them to question any and all interaction you have with her from then on.
answered 4 hours ago
apaul
45.2k23153222
add a comment |Â
up vote
3
down vote
Well, sounds like you're interested in your friend's little sister and it also sounds like you're pretty set on pursuing a relationship.
So...
Let's take a moment to examine what sort of relationship you want to pursue with this young woman, cause if it was a young woman who meant something to me, that would be my first question. Are your intentions honourable? Do you intend to have some kind of respectful, lasting, and meaningful relationship, or is it just lust?
Admittedly I don't have a little sister, but I've had daughters, and if anything, that's probably a higher standard. You want the people who pursue the people you care about to treat them well. Any inclination that this pursuer's intentions aren't as pure as the driven snow, and all those nasty protective instincts kick in. You probably want to avoid those protective instincts. They may be bad for your friendships in the best case, and bad for your health in the worst.
Check your motives first. If you really want a real relationship with this woman, then proceed.
Next, think about your relationship with her brothers. Do they have a high opinion of you? Have they seen you behave questionably toward your previous partners? Effectively, would they think you're a respectable match for a young woman who means the world to them?
If you can check both of those boxes... Are you willing to risk all of these friendships for the relationship you might have with this woman? If that's even a question you have to think about, you probably shouldn't move forward. Because, doing this even in the very best circumstances, can and will, risk all of these friendships. Even if things go wonderful for years, if things turn bad, you should expect to have a falling out with all of these people.
Should you decide that your intentions are good, and that her brothers like and respect you well enough, and that it's worth the risks... Cause you will... Cause young love is like that... Brave, or foolish, or both... probably both. Talk to the young woman first. You're not asking her brothers for a date, you're asking her. She's your priority. If she likes you, and her brothers don't, they may get over it in time. If you ask her brothers first, she could and likely should feel somewhat demeaned and controlled.
(I realize that sounds counter intuitive given the opening paragraphs about the brothers respecting you, but bear with me.)
You'll be changing the context of all of these relationships. She'll need to see you as more than her friend, or her brothers' friend. And her brothers will need to see you as a potential brother-in-law. If you want this to go as smoothly as possible, and maintain those friendships, you'll need to seem like a good fit in both categories. But neither work if she doesn't like you, so that's going to be your first concern.
If she doesn't want to pursue something more with you, respecting that fully will be your best bet toward moving forward, without damaging all these friendships. (Another reason it'll be important to ask her before testing the waters with her brothers) Asking her brothers and then being shot down be her will likely lead them to question any and all interaction you have with her from then on.
answered 4 hours ago
apaul
45.2k23153222
add a comment |Â
up vote
3
down vote
up vote
3
down vote
Well, sounds like you're interested in your friend's little sister and it also sounds like you're pretty set on pursuing a relationship.
So...
Let's take a moment to examine what sort of relationship you want to pursue with this young woman, cause if it was a young woman who meant something to me, that would be my first question. Are your intentions honourable? Do you intend to have some kind of respectful, lasting, and meaningful relationship, or is it just lust?
Admittedly I don't have a little sister, but I've had daughters, and if anything, that's probably a higher standard. You want the people who pursue the people you care about to treat them well. Any inclination that this pursuer's intentions aren't as pure as the driven snow, and all those nasty protective instincts kick in. You probably want to avoid those protective instincts. They may be bad for your friendships in the best case, and bad for your health in the worst.
Check your motives first. If you really want a real relationship with this woman, then proceed.
Next, think about your relationship with her brothers. Do they have a high opinion of you? Have they seen you behave questionably toward your previous partners? Effectively, would they think you're a respectable match for a young woman who means the world to them?
If you can check both of those boxes... Are you willing to risk all of these friendships for the relationship you might have with this woman? If that's even a question you have to think about, you probably shouldn't move forward. Because, doing this even in the very best circumstances, can and will, risk all of these friendships. Even if things go wonderful for years, if things turn bad, you should expect to have a falling out with all of these people.
Should you decide that your intentions are good, and that her brothers like and respect you well enough, and that it's worth the risks... Cause you will... Cause young love is like that... Brave, or foolish, or both... probably both. Talk to the young woman first. You're not asking her brothers for a date, you're asking her. She's your priority. If she likes you, and her brothers don't, they may get over it in time. If you ask her brothers first, she could and likely should feel somewhat demeaned and controlled.
(I realize that sounds counter intuitive given the opening paragraphs about the brothers respecting you, but bear with me.)
You'll be changing the context of all of these relationships. She'll need to see you as more than her friend, or her brothers' friend. And her brothers will need to see you as a potential brother-in-law. If you want this to go as smoothly as possible, and maintain those friendships, you'll need to seem like a good fit in both categories. But neither work if she doesn't like you, so that's going to be your first concern.
If she doesn't want to pursue something more with you, respecting that fully will be your best bet toward moving forward, without damaging all these friendships. (Another reason it'll be important to ask her before testing the waters with her brothers) Asking her brothers and then being shot down be her will likely lead them to question any and all interaction you have with her from then on.
answered 4 hours ago
apaul
45.2k23153222
Well, sounds like you're interested in your friend's little sister and it also sounds like you're pretty set on pursuing a relationship.
So...
Let's take a moment to examine what sort of relationship you want to pursue with this young woman, cause if it was a young woman who meant something to me, that would be my first question. Are your intentions honourable? Do you intend to have some kind of respectful, lasting, and meaningful relationship, or is it just lust?
Admittedly I don't have a little sister, but I've had daughters, and if anything, that's probably a higher standard. You want the people who pursue the people you care about to treat them well. Any inclination that this pursuer's intentions aren't as pure as the driven snow, and all those nasty protective instincts kick in. You probably want to avoid those protective instincts. They may be bad for your friendships in the best case, and bad for your health in the worst.
Check your motives first. If you really want a real relationship with this woman, then proceed.
Next, think about your relationship with her brothers. Do they have a high opinion of you? Have they seen you behave questionably toward your previous partners? Effectively, would they think you're a respectable match for a young woman who means the world to them?
If you can check both of those boxes... Are you willing to risk all of these friendships for the relationship you might have with this woman? If that's even a question you have to think about, you probably shouldn't move forward. Because, doing this even in the very best circumstances, can and will, risk all of these friendships. Even if things go wonderful for years, if things turn bad, you should expect to have a falling out with all of these people.
Should you decide that your intentions are good, and that her brothers like and respect you well enough, and that it's worth the risks... Cause you will... Cause young love is like that... Brave, or foolish, or both... probably both. Talk to the young woman first. You're not asking her brothers for a date, you're asking her. She's your priority. If she likes you, and her brothers don't, they may get over it in time. If you ask her brothers first, she could and likely should feel somewhat demeaned and controlled.
(I realize that sounds counter intuitive given the opening paragraphs about the brothers respecting you, but bear with me.)
You'll be changing the context of all of these relationships. She'll need to see you as more than her friend, or her brothers' friend. And her brothers will need to see you as a potential brother-in-law. If you want this to go as smoothly as possible, and maintain those friendships, you'll need to seem like a good fit in both categories. But neither work if she doesn't like you, so that's going to be your first concern.
If she doesn't want to pursue something more with you, respecting that fully will be your best bet toward moving forward, without damaging all these friendships. (Another reason it'll be important to ask her before testing the waters with her brothers) Asking her brothers and then being shot down be her will likely lead them to question any and all interaction you have with her from then on.
answered 4 hours ago
apaul
45.2k23153222
answered 4 hours ago
apaul
45.2k23153222
answered 4 hours ago
apaul
45.2k23153222
answered 4 hours ago
apaul
45.2k23153222
45.2k23153222
add a comment |Â
add a comment |Â
netdenizen177 is a new contributor. Be nice, and check out our Code of Conduct.
netdenizen177 is a new contributor. Be nice, and check out our Code of Conduct.
netdenizen177 is a new contributor. Be nice, and check out our Code of Conduct.
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Is there a reason to think this is unethical in the US? She has already asked you out (prom) before, so it is not the first time you are out. What reason is then to consider that unethical? You should be more detailed about the problem you see.
– puck
4 hours ago
1
"Is this unethical?" Isn't really a question we can answer here. Ethics, despite popular opinion, tend to vary and generally fall into shades of grey rather than black and white, or good and bad.
– apaul
4 hours ago
Well the ethics question was a more tangential precursor to the main question, I suppose. Maybe I should have asked it in a more casual context. The prom thing seemed (but was not explicitly stated) as in a just-as-friends thing with a potential undertone. But my main thought is it kinda seems like an asshole move to go and date your friend's sister, but I've thought about the situation and figured Gary isn't Jennifer's keeper. However it still rubs me the wrong way and there might be an angle I'm not considering.
– netdenizen177
4 hours ago
Did you ever watch Harry Potter? He ended up dating and marrying his best friend younger sister. Nothing unusual.
– gnasher729
41 mins ago