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My best friend is a beautiful vibrant woman with so much to offer. Not just physically unnatractive. But he is gross to look at. Hos and has a bull ring in his nose. His personal shee is terrible, teeth rotting out of his face from being a chain smoker. Seperated for a very short time and claims his wife cheated on him which i have my doubts about that. Im waiting for them to break up but even that makes me feel like a jerk. She'll be sick of hearing the same shit and you'll be getting more frustrated saying it. You're getting too involved.

She's been there for you when things have been crap.

She's in a tricky situation now and she might need you. Put all your own opinions to one side and just be a friend. She knows how you feel about him now so she might be hesitant to talk to you about any problems, or the good stuff between them. A bottle of cheap wine and a load of junk food will solve all. It somehow always gets back to them. Ditto if they break up. It's so tempting to be like "what a fucking loser he was" until a week later and they love each other again and you're like shittt. Make an excuse to hang out with her in a totally platonic setting. Do some sort of vaguely excusable professional coffee.

Tell her you want to plan a surprise party with your brother. Just get two hours to chill out with her, and see whether your perceived chemistry is a real thing -- if you have the kind of bubbly, clicky conversation that we all dream about.

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If so, and if you still want to go ahead, then you have to take datimg painful next step. Tell Your Friend Yes, tell your friend that you plan to ask her sister out. But be aware that your friend might freak out, throw a drink in your face, put you in a triangle choke, and spend all night writing your name in his blood on the wall of his holding cell after he gets arrested. Or he could be totally cool with it. But there are some nasty possibilities here. Ask Her Out Whew! Now, just ask her out, like you would any other woman. Which is to say, suggest alcohol at a time and place, without apology, hesitation, or further explanation.

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