My friend and I once decided to simultaneously place personal ads in a NYC paper. I decided to place an ad because things were very slow on the boyfriend front, and it'd been a long time since I'd met a guy I really hit it off with. My friend decided to place her ad because she wanted meet someone outside her usual circle of angst-filled artists, who seemed to care more about their art than a relationship.

Our ads were completely different, and we were both looking for completely different types of guys. Yet despite the difference in our ads, we found similarities (both good and bad) in recorded messages left for us, and in subsequent phone conversations.

When I came back from a particularly bad date one evening, I commiserated to my friend about it. We started to analyze why the bad date happened, and how it could have been prevented. We brainstormed through our experiences, which led us to create the following guidelines, in an attempt to avoid additional wasted time and bad dates. In the weeks following the creation of, and adherence to these guidelines, we've decided they really do work.

If you have an interest in personal ad dating, we suggest placing your own ad instead of answering one. When you place an ad, you have a whole pool of guys to choose from, rather than just the one chance. (You could easily get 25+ responses if your ad is cleverly and carefully written.) But don't let the thought of an onslaught of responses overwhelm you -- with the use of these guidelines, wading through them will be a piece of cake!

Note: Many of the premises presented in these guidelines will also work for dating through Internet match-making ads.

Part I: Evaluating the recorded messages left for you

The first thing to pay attention to when listening to a recorded message is the guy's voice. If you think it sounds nice, and you're attracted to it, that's definitely a good sign.

Next, ask yourself: "Does this message sound inspiring?" and "Does this person sound interesting?" If the answer is yes to both of those questions, it's another good sign, but the battle hasn't been won yetÉ

In addition to the good characteristics a message may contain, there are also a substantial amount of undesirable things, which you'll need to keep a lookout for. Following are some key ones we noted:

Says little about himself. It's not a good sign if the guy hardly says anything about himself in his message, and then expects you to call him. The point of leaving a message for you is to say things so that you will want to call him. Example: If his message says something to the effect of, "Hi. I like rollerblading and going to the movies -- call me." If I were you, I wouldn't be grabbin' that phone too fast!

Uses tired clichés. Beware of clichés like "I'm looking for that special someone," "I'm interested in everything this city has to offer," "I'm tired of the bar scene" etc. Use of unexciting lines probably come from an unexciting individual.

Uninteresting. If he seems nice, but sounds a little drony, and nothing he says seems terribly interesting to you, forget it. There are plenty of nice, boring guys around -- is that what you want?

Brags about material possessions. Beware of a guy who mentions/brags about owning a fancy car, real estate, etc. Sure, it's nice to know the guy has money, but what's more important to you: a relationship with a great guy, or some fancy dinners with a schmo?

Mentions sex. If he mentions sex in any way, it's a bad sign. It's an inappropriate topic to discuss at this point in time with a total stranger.

Complainer/Negative. If the guy complains about his job, how tough things are for him, the crappy state of the environment, etc., it's not a good sign. If he can't sound positive in a two-minute message (which supposedly puts his best foot forward) it's highly probable much more negativity will present itself down the road. Is this the kind of person, above and beyond all others, that you want to be with?

Ignores your criteria. If the guy completely ignores specific criteria you listed in your ad, it's not a good sign. Example: Several guys who ate red meat left me messages, when I clearly specified that wasn't what I was looking for.

Answers a lot of ads. If you and a female friend place ads at the same time (and your requirements/content differs substantially), if you discover the same guy answered both of your ads, beware. It means he's not being very discriminating, and he's just "makin' the personal ad rounds."

Part II: Your First Phone Conversation

After evaluating the guy's message, you liked it enough to want to call him back. You pick up the phone to call, but before you do, remember these two pointers:

Dial *67 before you dial his number. Dialing *67 before a number prevents your phone number from being displayed on Caller ID. And if you hang up before your call is answered, it blocks *69 from being able to call you back. (Unlike *69, *67 is free.)

If you call and no one answers, don't leave your number on his machine. Hang up when you get a machine (out of curiosity, you can listen to his greeting before you do!). Call back a few times until you get him in person -- it's not a good idea to distribute your phone number to people you don't know.

During this first conversation, here are some important questions to ask him (they are also handy conversation-starters):

How old are you? If the guy knows your age and doesn't say his, beware: there could be a big age discrepancy. Example: My friend said in her ad she was looking for someone "near her age," which is 33. This one guy left her a decent-sounding message, without mentioning his age. When she spoke with him later, he still didn't mention his age. Finally, she had to ask, and he said he was 50. 50 is "near" 33? I don't think so! After that, we made it a point to find out age early in the conversation.

What are you looking for in a relationship? Find out the answers to all matters that you feel are very important in a potential boyfriend, so you don't waste time with conversations leading nowhere. Some things to find out: if he's looking for a possible committed relationship or just wanting something casual; his views on drugs and alcohol; if he wants to have kids, etc. Whatever issues are of key importance to you should be addressed initially.

What attracted you to my ad? If the guy says one specific word attracted him to your ad, it's not such a great sign. It should be the overall feel of the ad that attracted him.

In addition to keeping on the lookout for topics discussed in Part I, here are some questions to ask yourself:

Is he focusing too much on looks/sexuality? If conversation from the guy seems to have an over-emphasis on physical looks, it's not a good sign. Also, watch out if the guy mentions words like "sexy," "sensual," etc., or describes himself as "virile." You know, that type of stuff!

Did he ask me how much I weigh? If the guy asks your specific weight, it's not a good sign. We found in most cases, it was the jerkier guys who asked us how much we weighed. After all, all we just want to meet a nice guy, not audition to be a Playboy centerfold.

Is he avoiding answering reasonable questions? If you ask a reasonable, direct question like, "What's your job?" or "Where did you go to college?" and he doesn't readily answer, it's not a good sign -- it means he probably has something to hide.

Do I feel in any way interrogated in this conversation? If you feel like you're being given the third degree, or if the guy is making you feel like you have to prove yourself, it's a bad sign. Example: Similar to being on the witness stand, a guy once questioned me: "So what is it you do that makes you think you're so quirky?" Immediately, I was put on the defensive, and I didn't appreciate it. I knew this guy was a dead end street.

Is he dominating the conversation? If you feel the guy is dominating the conversation, it's not a good sign. He should be just as interested in hearing what you have to say as he is in talking about himself.

Does he show little tact or say dumb things? If the guy says something you think shows little tact, or is downright dumb, don't dismiss the thought! Are either of those a characteristic you want your boyfriend to have?

Has he dissed any of his ex'es? If the guy says mean things about an ex-girlfriend, it's not a good sign -- it's an indicator of bad character.

As your conversation is winding down:

Did we have good rapport? If you're serious about finding a boyfriend, good phone rapport is of crucial importance. You should have excellent rapport from the beginning, and when you've finished your first conversation, you should feel excited about it. If you don't have good rapport on the phone, chances are your rapport will be from worse to much worse in person. It's advisable not to meet if you don't have positive, flowing rapport on the phone.

And then:

Don't give him your number if you have any hesitations. If after the first conversation, you're not sure you want to give out your number or get together, trust your instincts -- DON'T! Say something like, "I have to think about how I feel and call you back." You've politely exited the call, without offending him or saying anything unreasonable. Later you can decide what you want to do.

Part III: If You Agree to Meet

It's highly advisable that he not pick you up somewhere. As was said a million times before, meet in a public place, and have a way of getting home.

Don't feel bad about changing your mind beforehand and cancelling. If at the end of your conversation you decide to meet, before you actually go through with the date, feel free to cancel your date if necessary. Example: I had an interesting, hour-long conversation with a guy who had six degrees, including a Ph.D. in philosophy, and I agreed to meet him. But before our date, I thought about it some more. I thought, "This guy's an intellectual, which I'm definitely not -- who am I kidding that this could really work out?" I called him back, and politely canceled our date to meet.

If you have any reservations, meet for a drink instead of dinner. If you have any reservations about how you'll get along, meet for a drink or coffee instead of dinner. It can be quite uncomfortable eating together if things aren't going well, whereas sipping a drink isn't nearly as awkward. Example: I agreed to have dinner with a guy I had some reservations about -- the date proceeded to be a disaster. After about five bites of my dinner, I waved to our waitress, and when she came over, I asked, "Can I get this to go please?" I could have tolerated a drink with the guy, but not dinner!