Try starting out as friends

Q. I run into the following situation somewhat often and wonder if I'm taking the right approach. I'll meet two ladies at the same time at a party or event. They are friends and came to the event together.

Had I met them separately, I would have asked each out on a date to see what the possibilities were. However, since they are friends, my thinking is that I have to pick one. Even though at this point you don't know anything about them, really, and cannot know how things will turn out, chances are you are slightly more attracted to one than the other. And that's really all you can go on or so I've thought. Or am I missing some angle? Some way to explore asking each one out to see which might be a better fit without disrupting a friendship?

-- Really Clueless

A. Please use your e-mail access to notify the authorities of your whereabouts; I'm assuming you're stranded on a desert island with two women. The alternative is that you're failing to notice the other 3 billion women on Earth, and I have yet to meet the guy who does that.

I do sympathize. No one wants to hit on Ginger only to find out Mary Ann was The One. But even setting aside my nonbelief in the whole concept of The One, the chances that you would meet two women cold, ask out one, get a yes, fall in love irreplaceably ever after with the other, and have that love reciprocated, aren't exactly staggering.

Certainly they're small enough for this to be the only reasonable approach: Get to know the two of them platonically -- in whatever way least resembles a two-actress audition -- for as long as possible, and then see if anything develops naturally.

If you approach one romantically and it doesn't work out, then you honor their friendship by not approaching the other.

In that rare case where you date one and then fall hard and mutually for the friend, you make a clean and honest break from the first one, make your pitch to the second, and see what she decides. If she wants to give it a try, then she lets her friend know (since she has the closer relationship). There's no pretty way to do it. You behave like a grown-up, and hope everyone else plays along.

Q. What's a realistic expectation for houseguests? When I say, "Make yourself at home," can I expect them to "make yourselves at MY home," or "make yourselves at YOUR home"? Meaning, should I expect them to treat my house as I treat my house (fairly clean, no clutter, etc.) or expect them to treat it as their home (messy, dishes everywhere, towels strewn, etc.)?

Thanks.

-- Washington

A. If these people were raised, and not merely excused, then you can expect them to follow the lead of their hosts, within physical and cultural reason.

If these guests have stayed with you before and you already know they're going to leave dishes and towels everywhere, then you can expect them to leave dishes and towels everywhere. To deal with that, you have three choices: Speak up, suck it up, or point them to a hotel.