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Adapted from a recent online discussion.

Hi Carolyn: I’ve known my brother’s friend for years, but I don’t know him well. I see him in a group setting every few months, and we have always been flirty. I’d like to get to know him better one-on-one but ... how?

I usually wait for the other person to initiate but that hasn’t happened here — should I take that as a sign?

The thought of asking him out makes me feel like my throat is closing up. The idea of a “date” and sitting across the dinner table from someone making small talk — hang on, my throat is closing up again ... OK, it passed.

How do people do this?! On a regular basis?!

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I’m going to be seeing him at a party in a couple of weeks. Do you have any ideas on how to go about this?

And if you’re thinking I should enlist my brother’s help in setting me up: He is very protective (and large and intimidating) and his friends are not “allowed” to date me. This could be why the friend is flirty but hasn’t tried to take it any further. I don’t care what my brother says, but he definitely won’t be of any help in making it happen. — Asking Someone Out

Dear Asking: Have you said to your brother that his protectiveness is anachronistic bull and that the only person who decides who is “allowed” to date you is you?

That’s where I’d start.

So much bias rides for free under the banner of protectiveness.

Re: How to ask someone out: How about just asking if he’d like to go for coffee, lunch, go to a ballgame, etc.? Keep it friendly and just maybe it can go from there. That’s how my husband and I began almost 40 years ago. — Anonymous

Dear Anonymous: Thanks. That’s really all there is to it — and yes, the sitting-across-from part is awkward at first, but so are a lot of things.

In this case, there’s an even easier path than a cold ask: They’re already flirty. Mid-flirt in a party environment is an excellent, relatively low-risk time for her to ask, “So, are we just flirting here, or is this going somewhere?”

Dear Carolyn: My fiance’s brother, who had had a few too many beers, made a comment that some people listening took as racist. I wasn’t there but trust the people who told me about it. I now have close friends questioning my judgment for associating with that guy, and for marrying someone close to him — and who, unfortunately, had to loudly take up for his brother despite not agreeing with what he said.

What else should I do, besides reminding my friends that my fiance and his brother are two different people? — Questioned

Dear Questioned: Unless there’s more to the “loudly take up for his brother,” they’re grabbing torches and pitchforks against the innocent, and that won’t stop racism — but might empower its apologists.

So see if there’s more: “Do I hear you correctly — I should drop my fiance because of something his brother said? I want to understand.” An indication that you’re willing to listen in itself can be disarming.

E-mail Carolyn at tellme@washpost.com, follow her on Facebook at www.facebook.com/carolyn.hax or chat with her online at noon Eastern time each Friday at www.washingtonpost.com.

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