I think there are a few difficult conversations that women normally initiate. Men, for the most part, will sit back and wait for a woman to bring these topics up. They're all for anything that does not disrupt that status quo. So, I thought we'd break down some of the more ...uncomfortable conversation that we all tend to have and the various situations in which we have them. =>The Online Dating Site Initial Conversation - If you're a female, sitting back and waiting for guys to write you will result in little to no results. If the guy is quality, you can bet he's being inundated with responses from other women. Let's be honest, though...unless your message is riddled with typos and bad grammar or you open with something cheesy like, "Hello handsome..." (Grade A Cheese and will always have me hitting the delete button in milliseconds when I get messages like these from men)...it's all about your picture, your age and your body type. Those are the first three things men look at, and that's before they even read your email. Sure, it's always proper to read the card first before you open the present, but this ain't no birthday party. We look at profiles first THEN the message. Men have short attention spans, so don't send them a missive. 3-4 lines is good, and you should reference at least one thing from his profile and ask him a question. Open with something cheery like "Hey there..." (I just read that "Howdy" is a good intro. YMMV on that one.) "Hi" is a little stiff. No net speak, although smiley faces are okay to use in order to convey tone. If you share a common interest with the guy, like wine, tell him about a recent tasting or particular flight you just tried. Really read his full profile, too, because more and more people are intentionally writing something "off" to see if people are reading their profiles. Plus, lots of people are including truths in their profile ad like their real age or whether or not they're really divorced and not just separated. Don't write something generic like "Hey, liked your profile and think we have a lot in common. Would love to chat." That screams cut and paste and makes you look lazy. Also, ladies, be mindful of something....self-confidence is great. Self-importance isn't. It's fine to tell someone you're witty, but don't go overboard and say you'll have him in stitches. Expounding on your own virtues is fine, just don't over do it. I had a guy friend tell me that using descriptors like "fiercely intelligent" and "whip smart" makes a woman sound full of herself. Same goes for you too, guys. Show, don't tell. Keep it simple and easy. Women dig the 2 paragraph messages. Men don't. If he's intrigued enough by your photo and profile, you won't need to sell yourself too hard in the initial message. GREAT RESOURCE: Geeks Dream Girl, Evan Marc Katz , EFlirt Expert Laurie Davis =>The "Ok, should I stay or should I go?" conversation after a casual hook-up - So, there you are, basking in the afterglow of totally anonymous sex. Small talk, small talk, small talk...and......scene. So, who exits stage left first? You do. Or at least you should be the one to bring up whether you should stay or go. (Another reason why you should take a guy back to your place if you're going to hook up..it's not safe for a woman to be out hailing a cab at 2am or taking the subway. Plus, it's cold out there!) Wait to see how he acts afterwards. More than likely, he's falling asleep because that's just the biological response for the male brain after climaxing. They're spent. The last thing they want to do is get up, get dressed and walk you tot he door, let alone the corner. If he gets all snuggly, and you're okay with that, then enjoy it. But if it is just a casual hook up then you really don't want to fall in to that trap and then get attached. If he's groggy and just laying there, just start getting dressed. If he seems surprised, don't fall for it. He doesn't want to look like a dick. Just say you had fun, tell him to take care and leave. Yes, you can figure out his super duper confusing door/lock situation on your own. =>The "What are you looking for?" talk - Date three at the earliest, and definitely before you sleep together. Remember, a guy is going to wait as long as possible to have that conversation. Not necessarily because he's trying to use you but because he needs to feel like he's moving along on his terms. Pull this one out on date one and you look like you've got the wedding all planned and just need to cast a groom. How do you broach this subject? You simply ask the question and tell him why you're asking. "I just want to know if you're looking for something casual or looking to actually date someone because I'm looking for XXX." Don't bring up commitment or long term potential. Saying that you're looking to date someone is fine. He'll get the message. As obtuse as some guys can be, almost all guys know that most women aren't looking to be part of some guy's harem. No need to tell him you've been hurt in the past or that guys have let you down. Don't heap all that on him because then he's going to feel obligated. =>The "Are you disease free/I have XXX" talk - Always be prepared. I'm kind of stunned at how many guys will try to hook up with women, go home with them and not have any condoms on them. I think a lot of men expect women to take care of birth control or assume we're on The Pill and think they are impervious to STDs. Have condoms on your person, but ask him if he has any protection. If he doesn't, and the situation really warranted for him to have planned accordingly, then I'd be wary. That would make me worry that he goes bareback often. The time is well past where women who carry condoms look "easy." Listen, call me a big 'ol slut all you want. That's better than having herpes or HIV. Before the clothes come off, because at that point neither party is really thinking clearly and will pretty much believe anything, ask him the last time he was tested and whether or not he's ever had an STD. Listen to him closely. If your instincts jump even the slightest bit when he gives you his answer, be on guard. Our brains know so much more than our conscious mind can process at times. Trust your gut. I'm going to say this and it might be a tad controversial...but this whole "we agreed to both get tested before we slept together/once we decided I'd go on the Pill/before we went bareback" thing is a bunch of hooey. We say that because we want to look responsible. But the reality is, you shouldn't be waiting for a relationship to get tested anyway. And few men are in a rush to go to a doctor and have their pee pee prodded and swabbed. And guys, let me tell you, it takes sometimes weeks to months for women to get an appointment with their gyno or even Planned Parenthood. That's why you have to be vigilante and up to snuff with signs/symptoms of STD infection, genital warts , herpes, etc. People will and do lie. If you have herpes or HIV or any other STD , then that's something you bring up well before you ever get to the point where the clothes come off. Just come out with it, but be informed and be able to walk them through what your particular condition actually means for you and them. Know the risks, know the likelihood of infection and tell your partner. Depending on where you live, you may not have a legal obligation to disclose this information, but you do have a moral one. And avoid, at all costs, the "how many partners have you had" talk. It's irrelevant and none of your business..or his. =>The "Where is this going/Are we exclusive?" talk - This conversation should be saved for AT LEAST a couple months in or until you and your partner have established some kind of consistency and regularity. Ladies, just understand that a guy might pull back or seem hesitant. If he does, and everything up to that point has been pretty smooth, then let it go and drop the subject for a small time. Like a month or six weeks. But if you hit the four month mark and he's still not committing, then you need to figure out if this guy is worth the emotional investment. If he's not committing to exclusivity at least by this point..I'm guessing either he never will or never will with you. A man , even if he sees no future with a woman, will prolong a relationship as long as things are for the most part okay. A lot of men don't need to see a future with a woman to stay with her long term. Never assume exclusivity. A guy will keep this subject off the table for as long as he can in order to think he still has options, even if he doesn't. Again, there's no need to inform him that you're looking to get married and have kids and don't want to waste your time. That's a great way to scare a guy off. Your schedule and biological clock is not his problem. Just ask him straight out if you and he are exclusive. Which is not "Are you sleeping with anyone else?" That's a great way to put a guy on the defensive, especially if they are. Once they go on the defensive, it's going to be a bitch trying to get them to open up and be honest. That's their survival instinct kicking in. Just ask him the question at the appropriate time, not before sex or late at night or early in the morning or when he's been drinking. And DEFINITELY not in public because guys are terrified of public outbursts or scenes, so they're likely to clam up or tell you what you want to hear.And if he doesn't give you the answer you need, don't threaten to walk unless you're damn skippy sure you will. Go back on that kind of declaration once and he'll never take you seriously again. Ultimatums are not a woman's best friend. No guy is going to cave because a woman threatens to not have sex with them or bail. They'll just go have sex with someone else until you break down and give in. FACEBOOK - http://www.facebook.com/christanmarashio TWITTER - http://twitter.com/Moxieinthecity DATING QUESTIONS NEEDED!!! - Want free advice from dozens of other national and international singles? Ask Away. It’s Free! YOUR DATING ADVICE QUESTIONS HERE: http://moxieinthecity.net/ask-email.php