My best friend's older sister?

[dman145]

I have a crush on my best friend (of 16 years) older sister. We're both 21 now, and she's 23. By now his family is a second family to me and vise versa for him, so I never really saw her as anything more than just his annoying older sister. Judging by how she treated me growing up, she probably viewed me the same way. Just recently she started coming out with her brother to the bars a bit more ever since returning from college (I hadn't seen her in a few years). I can honestly say that I see her in a completely different light. I've joked around with my friend about hooking up with his sister and he has no issue with it. He said that he wouldn't care if I wanted to date her.



The problem is this; it just feels so stiff and awkward. There's been a couple times when we're alone and I feel like I have no idea what to say. We just sort of glance at each other, look away, and maybe say a comment or two. Rinse and repeat. How should I go about this? I'm meeting up with her, my best friend, and my best friend's girlfriend for a Halloween party on Saturday. I feel like this is a perfect set up, but I have absolutely no idea how to even flirt with her. It's so hard to see her as just another girl and flirt like I would anyone else.

[Ejizzle]

Ah, yes. The "Best friend's sister" angle, huh? I've been down this road a few times, successfully. It's a very intriguing path to go down.

Now, the main thing here to remember is that this is the sister of your best friend. Duh, sounds obvious, right? But many people forget that, and just flirt like it's any other girl. Nay nay, don't do this. I mean, chances are, your best friend has heard many a story about how you flirt with girls, what you think about the hot ones, and what you may think negatively about an old fling or an ex. All of this will come to light in his mind once you legitimately pursue his sister, and he probably will be at least a little apprehensive about this.

That said, that's the only real bad news about this. As long as you are respectful, your relationship with your friend should be fine.

Now, the sister is another story. She may be hung up on the days where you used to eat paste, and may never see you as more than, like you say, an annoying little brother. But if you can make it clear to her that you're interested, she'll definitely consider it, and probably think about it a lot because it is quite the conundrum. Stay calm, act natural and get your point across; you'll win.

DO'S for the party:

Casually flirt with her

Read her signs - if she's not feeling it right away, back off, try again later

Show your more mature side

DON'Ts for the party:

Don't ingest too much liquid courage - sloppy is childish and you don't want her seeing you childish

Grind overly sexual with her. This will strain your relationship with besty.

Try and take things to a bedroom. Obvious reasons.

Just try to keep the mood light, man. You can do this, it's not uncommon.

[Lommelun]

I agree. Thought of giving an answer almost like this. No need now.

[dman145]

Great advice man, especially the do's and dont's. I'll do just what you said. Although I was tempted to take things to the bedroom if the mood was right (she has offered to let the three of us stay at her apartment for the night) but I'll refrain from doing so. Thanks!

[jacquesvol]

Had it twice, once my best friend's kid sister: she was very interested in me (she was 13, I was 16), I pretended not to see her obvious efforts. A few years later -at 18- another best friend's twin sister got very interested in me but it wasn't mutual, I pretended not to see though it was obvious too.

The final joke is that they both married brothers who were friends too.

Indeed, it feels so stiff and awkward.I know my friends wouldn't have objected (the twins were protective toward each other)

[1inmillion]

You are risking your best friend of 16 years by dating his sister. I know he said its OK but if something would go wrong with you and his sister, you could loose his friendship. I would advise not to do it.