My friend hasn’t had sex in a long, long time, like almost a year. She is young, attractive, but has a really time consuming and emotionally draining job. How can she find a guy to break this dry streak if she isn’t a fan of a one night stand?

Wow, you’re not kidding. A year, that is a long, long time. Especially if your friend has the looks. I don’t mean to doubt your honesty, but maybe she isn’t as hot as you say she is. I mean… A year? In New York City? Seriously?

Ok, let’s say this isn’t a prank and that your friend really is young, attractive and somehow can’t seem to get laid. Has she really tried? The city is full of horny young men who will gladly sell their own mothers for a taste of the forbidden nectar. Just make sure she is wearing something moderately sexy (try to avoid anything like this), take her to a bar, any bar, and sit there. Yes, you heard me, sit there. That is all. Maybe giggle a little. Have a drink. You can be sure that you won’t have to pay for the next one.

Now, you do point out two important obstacles to a happy sex life. Let’s talk about the job first. Granted, there are a lot of jobs out there that make it very hard for anyone to have anything vaguely resembling a social life. But as long as your friend doesn’t study the apes in Cameroon (I hear it is a full time gig), she should have time for a drink at some point. What’s more, she might actually need it a lot more than the rest of us lowly mortals. As long as she doesn’t start talking about work with Mr. Potential Prince Charming, you’re good.

Ok, so, draining job, check. Now with the other, perhaps more threatening obstacle: the infamous one night stand.

I gotta ask, what do you mean when you say “she isn’t a fan”? Are we talking chastity belt for the first 5 dates, or does she just have a poster that says “If you put out he should call you” above her bed? Chances are, she’s just looking for a nice guy who will call her back, maybe take her out for some Chinese food and listen to her problems a little before savagely ravishing her. Don’t worry, those guys exist. Believe it or not, we are not all a bunch of sex-crazed animals who are incapable of having a decent conversation to save our lives. Just an overwhelming majority. Anyway, back to your friend…

You know what, screw this. I was about to give you a detailed, Machiavellian plan to make sure your girl gets laid no matter the circumstances, but really, this would be a waste of both our times. In truth, there is only one answer to your question: Tequila shots. That’s all you need to know. Get some tequila into her, and the universe will take care of the rest.

I have been with my boyfriend for 2 years, and I love him a lot. I’m worried that he might be struggling financially and I want to be able to help him. I’m in a place right now where I can afford to help him out but I’m worried he’ll be embarrassed and lash out. What should I do? 

Financial struggles are a thing of the past, haven’t you heard? The struggling artist is dead! I can only imagine your boyfriend is an artist, or you’re hiding the fact that he’s unemployed, which, by the way is okay. The easiest thing to do is to sit your boy down and have a little chit chat action, but in reality that’s also the hardest. Confronting the matter head on will make that turtle’s head pop back in it’s shell quicker than you can say, “I support you.”

The major thing you have going for you in this scenario is time. You two have been together for two years, so there are ways you can broach the subject that make it seem like a natural progression in your relationship. This all depends on how comfortable you are with him, but “I love him a lot,” usually means that you love him… a lot. It’s around the two year mark that you really should be making the next step into living together. That’s also cost efficient as you’ll be splitting the rent then/ If he has roommates, you might have to suck it up for a little while, ditch your digs so you can help him out with his. Hey! You love him a lot, right?

If moving in together is too big of a leap for you, ask him if he’d be interested in opening a joint checking account. Red flags may go up in his head, but explain that it’s not about marriage, it’s about reliance. How your partner handles money is a real determining factor on your future together. You don’t want to have an empty checking account while little babe Tommy is crying for some warm milk. See what kind of a man he is, and maybe this will explain why he’s “struggling.”

Check online for discount rates, deals, etc. If you guys want to go on a date, have the coupon ready and present it at the end of dinner, any sooner and it’ll spoil the evening. When the check is plopped down, he’ll be too full to argue, and might even appreciate the gesture. He shouldn’t get pissed about it, if he does he’s kind of a tool. Deflect by telling him that things aren’t going so great financially for you either, this should motivate him to work harder. If it doesn’t, then he’s definitely a tool.

DO NOT try getting him a job where you work! EVER! Encourage him to consider other areas of employment, but make sure they’re far as fuck from where you work. You need space in a relationship. Relish it. If all else fails, dump the tool and give me a call. I’m always happy to be a kept man.

I have had a crush on a friend of a friend for a while now, and he recently (about 2 months ago) broke up with his long-term girlfriend. We got a bit tipsy and hooked up a couple of weeks ago, and I think he’s a bit freaked out. I really like him, am really regretting my inebriated mistakes, and I just don’t know what to do! Is there a shot at something still happening there, or have I screwed it all up?

Ahhh the ol’ dip your toe in the water game, eh? Checking to see if maybe the water is warm enough that you can strip your clothes off and swim in bed for an afternoon or two. What is lacking from your question, and is seemingly a telltale sign, is whether or not he has had a crush on you all this time. It’s good that you waited those two months, because if you think he’s freaked out now, I can guarantee you would’ve woken up with a chicken scratch note on your pillow if you had acted any earlier.

So, have you screwed it up? No. There is something salvageable here. From the ashes may rise a relationship, or a continuous hook up. Or whatever you want. But right now, back off. Give him space. The reason this hook up happened to begin with, was because at one point you seemed unattainable to him. You were his friend who he could talk to about relationship bull, grab a beer, hang out, etc. And in turn he found out about your love life, which gave room for the maturation of friendliness to sexiness. But in the leap and bound the two of you took, the mystery is gone.

GET IT BACK!

Be laid back. Don’t let on that you care. Flirt with other dudes. I hate game playing, but in this case it’s the only thing that is going to work. You need to fuck with his head any style you can. If he flirts with a girl, don’t try getting possessive. Don’t make that snide joke that you think is cute, “Hey, which one of us are you going home with tonight? Hahaha, no I’m kidding.” Well it’s not funny. It’s creepy. Just let the shit slide for a while. Either he’ll come to you, or he won’t. If he doesn’t, then in the process of making him jealous, maybe you’ll find yourself a new beau.

I’ll tell you straight up though, the girlfriend thing shouldn’t have anything to do with his reaction. I know it takes a while to get over your ex, but two months should be the max (unless he’s hooking up with her behind your back, in which case you need to drop the whole situation because that’s a Western mess). If the hook up happens again, make sure it happens under sober circumstances. Drunken hook ups are what they are, an act of disrespectful lust (awesome), but if you want more, get it done on sober terms.

I’ve started dating someone and we get along really well. We have romantic dinners, great conversation and so much in common. Problem: the sex is well…boring. I’m a girl who likes to have fun in bed and I’m just not gelling with his…ahem, style. Do I run? Do I say something? Sex is important but I really like this guy!

It doesn’t sound like you really have a problem. It sounds like you have a friend… Or a puppy. Or a kitten for that matter. Maybe a well domesticated monkey, which should absolutely be a legal pet and companion.

“Sex is important,” for single people. It’s something that is craved, desired and needed. It sounds like you’re looking to nail this guy down to a solid future, a relationship (cue the scary music). In which case “sex” is not “important.” GOOD sex is important. Necessary really. If you’re unsatisfied in the boudoir, it’s going to lead to passive aggressive tendencies. It might manifest itself in snide quips that you brush off as a little joke, but it will then transform into bigger and worse problems and eventually one (if not the both of you) will feel very shitty and end things for good. No relationship. No friend. Not even a domesticated monkey.

If you are the introverted type who believes that it’ll be all hunky dory because you’ve got a really great guy to talk to, and hey, “what’s a vibrator for anyways?” Don’t be so smug. If you’re not enjoying yourself, eventually he’s going to catch on, which will lead to his lack of enjoyment. He’ll start questioning his abilities and feel like less of a man, and since men have too small of a brain to compute that this could in fact be their wrongdoing, he will take it out on you rather than himself. Or he’ll take it out on you verbally, and psychologically take it out on himself leading to a dinky winky when engines need to be a-booming.

Don’t fret, there are ways to deal with this. If you’re really clicking with this guy and want it to work, confront him. Dude sounds like a dreamboat, so I’m sure he’ll be able to have an adult conversation about matters in the bedroom. If he’s the sensitive (i.e. Macho) type, try talking about it in a way that sounds sexy. Suggest trying something different. Role play. Dirty talk. Whatever gets your gears in motion.

Of course you should also keep in mind that perhaps it ain’t his problem, which is NOT to say it is yours. Some people don’t have the chemistry, and if that’s the case nothing can be done. I don’t buy into the whole astrological sign vs. sign bull shit, but I do believe in bodies telling you what feels right and what doesn’t. Listen up, she might be trying to tell you something…

I’ve gone on a couple of dates with a guy, and the chemistry just isn’t there. We sit at dinner and force conversation, or sit awkwardly staring at our plates. Then you get some booze in us (not a lot, mind you) and the conversation flows like nothing else! How do I know if this is worth continuing to pursue, and when is it time to just move on? 

The time is now. Wherever you go, there you are. You’re there. You’re at that time. Move on. I’m a neurotic white Jewish man. Funnel some booze in my mouth and I’m sure I could have a perfectly charming conversation with the Fuhrer. That’s what alcohol does. It makes you loquacious, eases you into insensibly numb attraction. And while you think that you guys are having an intellectually stimulating conversation when your eyes are in the back of your head, I’ll give you the translation of actual events.

Him: “Oh, I love D.H. Lawrence.” I have smooth soft hands, that will fell nice against your skin.

Her: “His prose are poetry.” Why is he talking about D.H. Lawrence? I’m ready to go.

Him: “But enough about that. Let’s get the check.” She’s ready to go.

Her: “I should probably take a cab.” We should go home together.

Him: “I’ll get you one.” We’re going home together.

It’s like a scripted dialogue and you both are the actors. If you’re unable to be sober with another individual for the span of an hour, having a fully linear conversation: THE TIME IS NOW!

If you’re still on the fence about it, find an activity the two of you can do devoid of boozing. Take a walk in Central Park. I’ve found that movement naturally produces conversation. When you’re sitting down looking at the other person, without anything else to do, it’s awkward. It feels forced. Get your feet going, and see if that gets the jabbering going. If you both are doing a whole lot of “scenery watching,” rather than fun talking… THE TIME IS NOW.

Get to know someone first. And no, asking if they have been tested before the act does not count as a Proustian interview. Unless this is someone you have known for a very long time and you guys are “giving it a try,” there is no possible way either of you could be comfortable going between blankets. Booze of course would take care of this, letting your inhibitions loose, but that most commonly ends with a 7 a.m. walk to Duane Reade for a little Plan B action. (Don’t act like it doesn’t.) And if you have known that person for a while and you are giving it a try, that is a major shift from: let’s go grab a beer and shoot some pool tonight friend-o.

Now, if you’re dead set on getting yours on that very first date, I can’t stop you. But I might be able to help you based on what you’re looking for. If you’ve been on the market too long and you’re looking for the GF clause, you’re knocking yourself ten steps back by jumping in the sack. “But we drank a lot, and he’s really hot and respects me.” If he respects you, he’ll respect your needing to wait. If he doesn’t respect that, he’s a chump. If you’re the chump and you’re looking to jump his bones ASAP, go against all post-coitus instincts. After you have sex, get out of there as fast as you can. He’ll try to make a whole kerfuffle about it, but have your BS meter on high. How is he saying, “But no babe, I really want you to spend the night”? Is there that high inflection in the back of his voice? Yup. That’s what we call lying. And that’s cool darling, because you’re not going to fall for it. You’re going to make him feel used, because every guy wants a little holding time after sex. They jostle, jab and joke about it, but if you leave him in that dark room alone, I guarantee he’ll curl up with a pillow so he can get some of that snuggle fever covered. This also (and I’m aware that this is retarded, but guess what, so are men) will make you seem cool. Like you are a hip little chick. Don’t need no man to make you feel whole. And in that message, the man will wonder if he could possibly ever be the man that you’d want to spend the night with.

In initiating the sex if, once again, you can’t control yourself. Gently let your gentleman caller know you are a sexual being, but don’t oversell it. You should not be talking about your view of sex as a fun thing you like to do. No. Be the strong, sexy, confident woman you are. Let them know that you are in touch with your sexuality. If you’d like you can say that you enjoy sex, but anything that might come off as “I get around,” can be dangerous, so play this one close to your chest. Be very subtle, with just enough innuendo that it gets his mind-a-movin’. If his mind is moving, you really should get out there, because you’ll be leaving him wanting more. It doesn’t matter whose place you go to, though, if your dude has a roommate you should really ask yourself if this is someone you want to have sex with. Grown man + roommate = some sort of trouble.

Now, if you’re just looking for a little slap and tickle, then go all out. Sex is fun and we sometimes crave it. If you’re just looking to get it out of your system, take your shots, talk about how much you love sex and take him home. It doesn’t mean anything tonight and it sure as hell won’t tomorrow.

Have I been living under a rock for the past ten years? I am completely incapable of playing “the game”. What are the rules? When do they apply? Help!

Disclaimer: The following post is in no way a statement that men are the sex that should be pursued. In my total and utter belief, the old renaissance idea of courtship is ideal, complete with white powdered faces, pocket watches and line dancing. However, given the nature of this question I will be focusing on the ways to pursue a man based on the relationship you seek. I am unable to write about how to pursue women in this way, because I am simply NOT QUALIFIED! You are a far more complex creature than we troglodytic Neanderthals, and should be respected as such. Given this disclaimer, the following is not a “He’s Just Not That Into You,” sort of self-help post. If he’s not into you, drop him. He’s not worth wasting your time.

One Nighter: Men aren’t the only ones who need sex. Fact. It’s not talked about as much, and the old double standard of “player” to “slut” is a sad thing in our (somewhat) evolved present. Women should enjoy their sexual appetites to the fullest of their capabilities. We only live once, right? Even so, if you’re really looking for a quick hit and run, best not to talk about it with your friends. They will try to discourage you, which will in no way help loosen your inhibitions for Rompfest 2012.

It’s a common misconception that in the pursuit of the male species women should go out and group up. We men are children. Very sensitive children. It’s hard to move past the cowardice of breaking the ice with one woman, much less seven. By all means, go out with your girlfriends and be on the hunt, but I recommend you split off from the group as quickly as possible. Plant yourself in densely populated area (i.e. By the bar, on the dance floor). Engrain yourself as part of the crowd and at once removed from it. When the right guy asks to buy you a drink; think about it for a second. Do not immediately nod your head. Think it over, shrug your shoulders as if to say, “why not,” and head to the bar. Play the mysterious one.

You’re most likely in a bar or a nightclub, there are too many aural and visual stimulants for us to comprehend long drawn out statements, so make physical contact. If it’s a younger guy you’re looking for, play with his hair. He’s still vulnerable to mommy syndrome, and this coddling will have him cooing in your hands. If it’s an older man, go for forearm or upper arm. It’ll give him a chance to feel muscular and at ease. If you’ve gotten this far, you’re in. Take him home and kick him out. If he wants to take you out and you’re into it, then go for it. If you don’t ever want to see the dude again, tell him you have a boyfriend. It gives him a story and lets him down easy.

Sex Buddies: Ahhh doom of the doom-ed. That fickle two-backed beast of mischief: sex buddies. Friends with benefits. Fuck buddies. No strings. The tango of the tempest. If you really want to give this a shot (and I highly recommend that you do not) you will need guile. You should already have someone in mind, most likely a new male friend. There should be obvious mutual attraction, but the way you two can hang should be right on the line of romantic and platonic. “Grab dinner, and then grab a beer?” Perfect. Eventually the topic of sex will come up, and this is where the tricks begin. Personally, I’ve found that women I’ve had casual sex relationships with tend to start off by saying that they don’t get emotionally connected to most of the men they sleep with. They say this as if to put me at ease. I’ve talked to other guys about this as well, and they agree: WE DON’T BELIEVE YOU. It only freaks us out more. Immediately our mind races to the thought, what if I’m the first one she likes… We get scared, and wait for the inevitable. Even if it’s true, why talk about it? What good does it do? None. Prove it through action. Allow yourself to be seen as a sexual individual. Talk about how you take pleasure in sex, this gets us thinking about what it would be like to be with you, rather than the cold mentality of, “I don’t ever get attached.” Once the relationship begins be ready for drama on either side. One of you guys is going to try turning this into a booty call, and there is a definite difference between the two. You need to be mature about it. Remember that you started as friends, and have now integrated sex into the great relationship you had before. Don‘t let things get weird, making it solely about the sex. It will dwindle into rage and hurt feelings. Always have a back up, whether it’s someone you’re casually dating or just someone to boost your ego on the nights when your fuck buddy is being an idiot. This goes for men as well. Feelings will get hurt if all energy is focused on one individual when something as personal as sex is handled immaturely.

Relationship: This is probably the simplest of all. Weird, right? There’s just one major factor to it. Wait. Dear God WAIT! If you seriously want a relationship with the dude you’re seeing (and be sure you do), wait as long as you possibly can to have sex with him. When men sleep with someone on the first date, they lose interest in the personality. Their brains kickstart from getting to know you, to getting laid by you. The getting to know part is when you find out about compatibility. I’m not saying pull a Sister Mary; foreplay is more than welcome. Go to town on it, and make sure he reciprocates. I’m just saying, no penetration for the first few weeks, and the longer you can hold back everything else, the better off you’ll be. Do not get possessive or needy, think about how big of a turn off that is when guys are to you. What goes around comes around.

WHY HASN’T HE CALLED?

“Why hasn’t he called?” The age old question. Let’s go through the rundown.

- He lost his phone and you’re over-thinking it. How many days have passed anyway? Oh. That many? Scratch that, he’s got his phone and you need to stop thinking about it.

- You had a piece of spinach caught between your two front teeth during dinner, which reminded him of a phobia he had buried deep down below the surface of his soul. Seeing you would mean dealing with this issue, which means dealing with emotions, and problems, and relationships. Some guys don’t like taking a look below the surface of the pond. They accept that fishes are swimming under there, but don’t try catching them.

- He heard “Pave Paradise,” and thought what a great concept that was. Maybe Joni was onto something there. So you’re his paradise, and he paved over you, trying to figure out what he had after it was gone. Men are a fickle idiotic creature, but such is life.

- You farted. He knows you farted. It’s cool and everything but… you farted.

- Why haven’t you called him?

- You have called him. Way too many times. You’re freaking him out, seriously.

- You sent him an e-mail the next day, full of oldies. In the message you told him that you thought this might brighten his day. It didn’t. It creeped him out. But it was thoughtful of you.

- It’s the Sabbath.

- He just got out of a “bad break up” and needs some time to “heal.” But verbalizing this would create a cliché. Better to just ignore you. You’ll probably figure that out for yourself, right?

- You’re too much for him. In every way. In the best of ways. He sees a future in your eyes. Your mirth. The way your skin glows in the candlelight. He felt himself falling into the end, and while the left half of his brain said let that happen, the right side said, these days aren’t over yet. Must. Live.

- He called you back a week later and suggested drinks. You jumped at the opportunity, not aware that what he meant was I want to keep you on the line, so when I feel lonely, I can remind myself that people actually find some redeemable quality in me. In doing this, any redeemable qualities are abolished. He’ll realize this later in life, but you need to realize it now. If he didn’t return your call the day of, “HE’S NOT THAT INTO YOU,” And that’s cool baby. You’re in Manhattan. Take a walk through Whole Foods.

- You’re vegan. He’s not. It’d never work. Come on.

- Because you concern yourself with questions like “why hasn’t called,” rather than refocusing that energy on something productive. He’ll call or he won’t. By next week it’s not going to make much of a difference anyway.

Send your questions to asmith@manhattanmedia.com or via twitter @N_YPress.

Question of the Week: I’ve been seeing someone for almost six months now, and I think I’m falling hard. There’s one major catch…He’s had a girlfriend for almost three years. He keeps telling me he’ll break up with her, but nothing’s happened yet. What should I do?

Awww, c’mon man. Do you mind if I call you “man”? Because you are very clearly acting like one. Is the sex really that good? I have to imagine that’s what’s anchoring this thing down, because any dude that’s had a girlfriend he’s been cheating on for (at least) six months out of the three years they’ve been dating is not a “nice guy.”

Let’s go to the furthest hypothetical possible.  Say he makes good on his word. He dumps his main squeeze for you, and everything is hunky dorey. You take walks around the West Village. Hit the Green Market and blow on hot apple cider together. Peachy. How long is it going to be before you piece together that this guy that you’re now exclusively dating, could very easily be cheating on you, as he did his ex? Sure, at first you’ll tell yourself it’s ridiculous. But soon the claws are bound to come out. Maybe he’ll be late for a dinner. Maybe he’ll go out with friends and come home in a black out state that wreaks of perfumed perfunctory. Think how simple the word rage is. It’s four-letters. That’s all it takes, four letters for a complete and total mental breakdown. Sick.

Now let’s go to the nearest (and most likely) hypothetical. He doesn’t break up with his lady love. You’re still seeing this dude, while he’s getting his from the gal next door. It’s gotta worry you that’s he’s been able to get away with it this long. I mean, damn, that’s some Dana Carvey “Master of Disguise,” type espionage. This dude’s gotta be a lying machine. If he’s able to lie to his girlfriend and say, “Naw babe, it’s the weirdest thing, my little nephew Tommy fell into the blue whale tank at the aquarium, and I just happened to pull him out and only stain the groin region of my pants in the pool!” Think how easy it is for him to say, “I’m going to leave her,” to you.

Drop him. I know right now it seems like you’re not going to find anyone as great as him (what?!), but think about all the other guys you’ve thought that about. Now try remembering how they turned out. Oy gevault. There’s nothing more baseless than a cheating lover. It means they are able to constantly deal with guilt. Adapt to it. Numb it. And big D or not, you’re gonna get hurt.