Messy situation & inhibitions...

[Fishy]

Howdy all, this is my first post here, nice to meet you folks.

I've got a bit of a predicament that I've stumbled into when I wasn't really looking, perhaps some of you could chime in with some advice for me. Here's the situation:
Characters:
Me
John
John Jr. (JJ)
Kim

So a little backstory is required. I've been friends with JJ for as long as I can remember, somewhere around since elementary school. We are both currently in our first college semester at the same college. For the past year and a half, JJ and his father John have been running a martial arts studio, which I have taken part in because I have an interest in MA's as a hobby, and I have a pretty good knack for it. Also present at the studio, among the other members, are John's other children, 3 daughters who include Kim. Over the past year and a half I have become a friend of the family for them, and as such am on a very informal relationship with all of them, even John, who's old enough to be my father.

So last year my sister, who is friends with Kim, informs me that Kim wants to know if I'll go to the semiformal dance with her. As a friend, I have no problem with that, so I agree and ask her. Afterwards, life continues as usual until later in the year, when it's prom time. In the same fashion as before, I asked Kim to prom, and we went and had a good time together. (John wanted her home early, and as my sensei, I was content to not keep Kim overnight) So life goes on, I graduated and she's in high school for another 2 years. I still go to the MA studio though, as does JJ.

However, since after prom I asked my sister if Kim had a serious interest in me, and it turns out she does. I felt kind of guilty about leading her on without really knowing (apparently she's either not much of a hinter, or not very good at it... or I'm not so good at picking up hints )

So here I am, tempted to ask Kim out. However, I cannot forget that JJ, who has been my friend forever, is her brother, and their whole family has a very close bond to one other. I have this inhibition that if I ask her out, I'll be endangering my friendship with JJ and risk disapproval by John. And these people don't just "go away" if I date her, they're her family.

So I'm stuck here, uncertain about acting, aware of the answer if I ask, but afraid of the consequences endangering what I've already got. Any advice?

[kronos51]

My advice: It sounds corny, but ask JJ and his dad first. Even though it technically is her decision to make, if you feel you might be offending them get their approval first, to show them that 1) you are mature and intend to treat her right, and 2) that you value their approval and opinion.

Just my opinion tho, good luck!

[Fishy]

Good advice, that's what I'm thinking my only viable option is coming down to.

I'm just trying to find out if there's an easier way (and there never is with these things! ) to go about doing this.

[kanzaki]

actually to me, i find nothing wrong going out with your best friend's sister.

But no matter what, ask ur fren first.

[Fishy]

actually to me, i find nothing wrong going out with your best friend's sister.

But no matter what, ask ur fren first.

I get this odd feeling that if I screw up, I ruin things with all of them. Stakes are pretty high and it's very awkward for me... any suggestions on how to go about doing this? Just pull him aside and talk?

[VictoriaEllen]

I would first talk to the father. His opinion matters the most beings he is your sensie and Kims father. If you do not get his approval, then there is no point in asking your friend. After you talk to the father, then talk to your friend.
But before either one of these discussions take place, I would do some serious reflection of what you think can become of you and Kim. What exactly are your feelings for her? Because, you are right, you would be taking a big risk in ruining a relationship with the family if something were to go wrong. So I would evaluate your feelings for her first.
The best way to ask is to yes, pull him aside at a conveint moment and just tell him you would like to have a private talk with him when he gets the chance.
Keep us posted .

[CalGal]

Talk to JJ informally/hypothetically about the situation. You will be able to sense his overall idea. You don't need the father's permission to just ask her on another date. And you should care more what the girl (Kim) thinks, not the father (who care about the martial arts?....which is more important, friendship, romance/girlfriends, or a sport?). This family would most likely be really happy to have you date her. They seem to have a high regard for you and are close with you. This said, you cannot hurt Kim in anyway once you start dating her. If it is going bad, make sure she is the one that hurts you and you don't hurt her (she will have to break up with you not vice versa).