Forget All the Moral Issues
Ok, you've found that sort-of-special someone and can't decide if you should go to the 'wanna come back to my place?' level. Forget all the moral issues that go along with sex and strangers, and let's skip straight to the questions that will help you decide if this guy has the potential for an amazing night of passion and ecstacy, or if he's just a big loser who will fill you with dread and remorse the next morning.

1. Is this someone you know from work, through friends, or from other social activities you do regularly?

   If the answer is yes, then forget about it. Do you really want to walk around the office thinking everyone is talking about that whimpering noise you make? Or imagine showing up to a friend's party and having to chat with your Cassanova with that, "I know you've taken me from behind on all fours, but let's just discuss this incredible spinach dip," grin on your face. It's just not worth it.

2. Do you really find this guy at all attractive, or are you just drunk and/or horny?

   If you are attracted to your new playmate, excellent. Go on to question three. If you have to think too much about it, that means you're going to wake up and not be able to look yourself, or your bed buddy, in the face. When you think back on your list of conquests you want to be able to say, "Hells yeah!" not "Oh, crap."

3. Did he use a cheesy pick-up line? And keep a straight face?

   If so, he's slimy and smarmy and most likely desparate. Stay away. (While we're on the subject, here's the line I've always wanted a guy to use on me: "So much depends on the weather. Is it raining in your bedroom?" But they're just never that smooth.)

4. Are you in a foreign country?

   If so, you're pretty much obligated to try out the local goods. It's part of the overall travel experience. Honest. It's just like that saying, "When in Rome, do the Romans."

5. Have you shaved your legs in the last 48 hours? If not, is he the kind of guy who's likely to comment on it?

   This may be a stranger, but that's no reason to come off looking like white trash. Ditto with the underwear situation. Are they at least sort of cute, or are you going to have a Bridget Jones, granny panties moment? That could seriously put out the heat, unless he's too aroused to care what's covering your crotch, so long as it gets removed. But you'd hate to get a reputation for having dumpy undies.

6. Are you going to be able to say "condom" in front of this guy and not feel weird?

   Be honest, are you at ease enough with him to make sure he covers it up, or are you going to be too shy to say anything if he decides to ride bareback? Nothing spells regret like genital warts or unplanned pregnancy, so inbetween the sensual full-body tongue massage and the frantic scratching and biting, roll out the glow-in-the-dark latex and play Now You See It, Now You Don't.

7. Are you woman enough to tell him how to please you?

   Once your companion has passed the test and things are getting steamy, don't be afraid to be assertive. Ask for what you want. You might not know him well enough to ask for a ride to the airport, but if you're adult enough to get naked together, you can tell him how to grope and grab you, and where and when to stick it. Stay open to new ideas. There's no point in broadening your sexual circle of friends if you don't learn some new tricks and have fun.

8. Can you see yourself chatting over breakfast with this guy?

   Of course you're just looking to get laid, but you don't want to face sudden awkward silence as soon as things go flaccid. I have great memories of one yummy Aussie, who not only kept me smiling and laughing all night, but then got up and made me bacon, eggs, toast, and fresh-sqeezed orange juice for breakfast, and wouldn't even let me help with the dishes. It was all very friendly and left me feeling satisfied inside and out.

9. Is this guy likely to turn psychotic and clingy and track you down and stalk you for weeks or months after the big night?

   This is a judgement call and depends on how perceptive you are to character flaws. If there's a clue that this guy may be unstable, such as talk of marriage, meeting his parents, settling down, or moving in together the next day, you might want to pass. Flying into a rage at the mention of ex-girlfriends is also a warning sign.

10. Finally, could you see yourself dating this person?

    If not, that's cool. You can appreciate someone for a night without being 100% compatible. But if you've found a guy you really dig, then for God's sake, don't mess it up with sex! Lots of guys are great for sitting there and looking good, but it's not everyday you meet one who's actually worth talking to. Enjoy the flirting and get his number to go out again. Anticipation is a major turn-on, so don't rush into the bedroom. Draw out the waiting and tempting and teasing, until you're both ready to explode.