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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

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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
    Commented Sep 17, 2018 at 3:56
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    "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
    Commented Sep 17, 2018 at 3:58
  • 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
    Commented Sep 17, 2018 at 4:04
  • I think it also depends on where your priorities are. What if Billy/Gary does not like it? Would you then be willing to not ask Jennifer out, and value your friendship above the potential relationship, or would you go for Jennifer?
    – Jeroen
    Commented Sep 17, 2018 at 12:49
  • why I was taking his sister to prom with some hostility in a joking manner This is key to understanding the brothers' opinion, but you'd need to be more specific. Was it actual hostility played off as joking? Was is a joke about supposedly being hostile? Was there an assumption that you wouldn't have romantic intentions and it's more a matter of two friends with no other prom dates? There are a lot of options here and they're not easy to distinguish between, especially when we only read your interpretation of events.
    – Flater
    Commented Sep 18, 2018 at 10:42

3 Answers 3

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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 by her will likely lead them to question any and all interaction you have with her from then on.

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    Why do you consider "just lust" as bad intentions? As long as he communicates honestly with Jennifer I do not see any problem.
    – QEDemonstrandum
    Commented Sep 17, 2018 at 13:31
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    @QEDemonstrandum That's clearly an ethical gray area, but one of those things that a brother is likely to take issue with.
    – apaul
    Commented Sep 17, 2018 at 13:47
  • @apaul: Your comment effectively results in acquiescing to a third party who wishes to restrict the lustful behavior of another person (Jennifer), when that person (Jennifer) has clearly indicated to want to engage in lustful behavior. Assuming Jennifer is an adult, that's not a good approach. Why would the brothers' (or family's, or anyone's) opinion on lustful behavior be more important than Jennifer's own opinion and intentions? When Jennifer and her brothers have immutably different opinions, OP will have to choose between Jennifer and her brothers, but OP is still free to choose.
    – Flater
    Commented Sep 18, 2018 at 10:33
  • @Flater I'm pretty sure that I covered that if you read the entire answer.
    – apaul
    Commented Sep 18, 2018 at 14:53
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Don't make things more complicated than they are. Ask her out and then just mention it to her brothers "BTW, Jennifer and I are having a beer on Friday". Not telling the brothers about it signals that you have something to hide. On the other hand, (neither) her brothers (nor her parents) (don't) own her. She decides herself (yes, even if she is below 18 or whatever "coming of age-limit" that is applicable) if she wants to go out with you. It is no one else's business.

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  • Being casual about it may backfire. It lacks signaling serious intent, which may lead to assumption as to OP's intentions. Comparatively, if OP were to make a bigger deal out of it, it implies that OP's intentions are more than just (at the other extreme) a one night stand. It very much depends on Jennifer's family which way you should lean in this regard.
    – Flater
    Commented Sep 18, 2018 at 10:37
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Jennifer wants to know what's on your mind before you talk to her brothers about it. Tell her your interested in adding romance to the relationship, but you're worried about how her brothers will react.

She did ask you prom, and you went together, that's pretty special. Without reading too much into it, I'd imagine the idea of romance has crossed get mind already. What does she think?

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