First Date DC

“but seriously, when should i call?”
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May 16, 2006

Sally wants Harry

settling? writes,

Here’s my question:

Several years ago, when I was fresh out of college, I started hooking up with this guy that was a former coworker - former because he had been fired from the firm about two weeks after I started. From what I remember, the sex was good, but this guy and I had a lot in common. Still do. He’s one of the truest friends I have ever had.

We ended the physical side of our relationship shortly after it started because he had a long distance girlfriend at the time and I wasn’t really interested in playing the other woman. But we have remained close over the years. I dated one of his friends seriously for over a year and got to know, and befriend, his now ex-girlfriend.

I’ve since moved about an hour away from him and though I do see him every few weeks when I’m in the area, and we talk and e-mail all the time, this weekend marks the first time that he’s coming to see me. I’m having a house warming party, and he’s invited. And since he’s a friend and the couch isn’t that comfortable, he’ll probably be sharing the same sleeping space as me.

Is it advisable to take this great friendship back to a physical level? He’s recently broken up from a serious relationship (she wanted marriage, he was against it) and I’ve been broken up with his friend for about a year and am happily single. But it would be nice to have good sex again.

Please, I’m begging for your advice.

Kathryn says,

I think we missed the window on your question - he may have already come to visit - but let’s pretend he hasn’t. Sorry ’bout that.

It sounds like you guys have already successfully overcome the sex partners-to-just friends transition once. I hope that means you could do it again, if you end up having sex when he’s visiting. His recent break-up and anti-marriage stance mean he’s probably not looking to start dating anyone right now, so I’m guessing, if anything, he’d only want some short-term physical comfort (aka a one-night stand). Please be sure to ask yourself if that’s ALL you want from him. If so, go for it, practice safer sex, and enjoy your time together.

Then, tomorrow, go back to bein’ friends.

DCB says,

Yeah, bang him, whatever. I don’t understand why an adult woman needs advice on whether she wants to have sex or not. I guess it’s only men who actually do what they want, instead of going through rounds of guilt-trip decision making.

May 15, 2006

This just in

Our friend Pinky, of “Landing the Guy” fame, has reported in on the outcome of her situation. Enjoy.

No guts, no glory

mr hanky writes,

I am in an urgent bind and I need your advice ASAP (hopefully before sunday). I am a freshman in medical school, and I told myself to stay away from girls because I wanted to make sure I could handle the allegedly overwhelming workload. However, as fate would have it, there was this one girl in my class that I found attractive. A lot of guys in my class also liked her and began talking to her, hitting on her, etc. I told myself that I would stay away from her and try not to talk to her as much in order to avoid being caught in the “friend” trap. So I made sure that whenever i did talk to her, it would be something worthwhile. I dont know if these signs meant anything, but in recent past she would always park next to my car in the parking lot, she would make some occasional teases about whether lexus drivers were pricks (because i told her the bmw/porcupine joke which you had mentioned a while ago), she would come to my side of the lecture hall and sit and talk with me during class breaks, shes heard that i am a great cook and always asks if i would cook for her, and on one occasion after class she asked me what i was doing and i said “going to the gym” and she said “oh” in a really disappointing manner (maybe she wanted to hang out?).

Finally I got the guts to ask her if she wanted to hang out over the weekend after I would run a marathon, and she said sure and gave me her digits. Now, what am i supposed to do? its been a while since ive really liked a girl…and i feel clueless as if to make a move the first time we hang out? should i be paying for her? what kind of restaurant should we hang out at? what kind of topics should the conversation be steered toward??? do i even have a chance with her? HELPPPPPPPPP!!! any help would be direly appreciated because ive dated many girls but never felt so pitiful/weak about one particular person until now. thanks

DCB says,

Well, start by being a man. You should do want you want to do, so if that means you want to pay then fine, but don’t overdo it. Don’t get caught up in trying to take her somewhere you think she will be impressed by. (I don’t suggest a restaurant for a first date because food will impede the absorption of alcohol.) Have you ever hooked up with a girl before? It’s not rocket science: go out, have several drinks, gradually get more touchy feely, sit next to her close, hand on back, and gradually move in until you start kissing. If she pulls away when your face is a few inches from her then she isn’t quite ready. As long as you don’t verbalize anything, you will be straight.

It’s really the girls job when it comes to conversation. I’m sure since you two are in the same class there is a lot to talk with school, but make sure to talk about fun stuff like cool experiences you’ve had and things you want to do.

Kathryn says,

What you’ve been doing so far is clearly working. Can you keep it up? Continue to be your confident self, with plenty going on in your life, not bothering this poor girl to death? Because she definitely finds it (and you) attractive. You’ve already accomplished the hardest part. Now you just have to ride it out.

I suggest taking her to one of those “great find” type restaurants, that has a cool atmosphere and is off the beaten path, but won’t cost too much money. Like Lauriol Plaza! (KIDDING) I’m not sure where you’re located, so I won’t waste time with suggestions. Something with a good wine list. Talk about the menu, what you like to cook, tease her about cooking for her “some day if tonight goes well” or something playful. Talk about your marathon training, and why you chose to do it. Talk about whether you’d ever do another. Ask her if she’d consider running one, and what other goals she might have, or past accomplishments. I think you have plenty of interests from which to draw conversational topics. Just remember to always bring it back to her. She’ll love it.

Good luck.

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May 12, 2006

Older man vs younger man

the woman psyche writes,

Older man vs. younger man

Older Man

Pros————————————–Cons
presumably established will die sooner than you
more experienced will die sooner than you
worldly will die sooner than you

Younger Man
Pros————————————–Cons
virile & eager not serious about relationship

Please finish this list….

Kathryn says,

I’m pretty sure I already wrote about this.

To paraphrase, Puppy pros:
- They generally believe I am their age or younger until I enlighten them. So they make a lady feel young.
- Have no problem drinking heavily any night of the week. Because sometimes, a girl needs a mid-week drinking buddy.
- Energetic and playful (arf! arf!).
- Stay up late, and don’t mind going out late. Or getting together late.
- Great for a No Strings Attached, Get Back In The Game type “relationship.”
- They can be awfully cute…

Puppy cons:
- Generally too young to be reliable; will flake on calling or getting together for any variety of reasons. Also known as “requires training.”
- Generally has roommates and/or young, stupid friends, which can occasionally be awkward. Also known as his “litter.”
- Has no problem drinking heavily any night of the week. Also known as “makes messes.”
- Almost never looking for the right girl to marry and have babies with, at least not any time soon. Also known as “still a kid.”

Please to note, internal age makes a much bigger difference than external age. I know 45-year-old puppies and 25-year-old men. Well, make that 28-year-old men.

DCB says,

Older man: Wants to settle down with you but doesn’t give you the “butterflies.”

Younger man: Fucks the shit out of you but for a limited time only.

May 11, 2006

Riding on the metro

metro girl writes,

So there’s this cute guy I see on the metro every day. I finally got up the courage to talk to him and now we talk the whole way to work. It seems I’m more fun than reading the Express, but I can’t tell if he’s really interested. We’ve had about 5 or 6 rides now together, and I realized I’m usually the one to initiate conversation. He seems a bit shy, but he always sits right next to me, as opposed to across the aisle, and carries on the chit chat. If he was gay or had a serious girlfriend would he still humour me and philosophize (yes, it’s a word, microsoft says so) on the way to work? Is he just passing time on an otherwise boring ride or could he just not be the type to ask a talkative stranger on the metro out to lunch?

DCB says,

It’s all about the initiation. Starting a conversation takes work, having one does not. Asking a girl out takes work, being asked out does not. Unless he is working for you, he probably doesn’t want you bad enough. One of your options is to hold his hand through the various stages of seduction, but I have a feeling that won’t really satisfy you. Stop talking and let him squirm for a way back into the comfort zone with you. Don’t make it easy for him.

Kathryn says,

Here’s the thing about Metro Romances: they are short-lived, generally impossible, and tend to fall into the daydreaming/no-impact-on-real-life category. For the most part, what happens on the ‘Tro stays on the ‘Tro. People like to flirt, exchange glances, and feel attractive. The ‘Tro offers boundless opportunities for this kind of attention, giving you a little extra spring in your step when you hit ground level. He could be gay or have a girlfriend or not consider you his type, and still be flattered by your interest in talking to him. That doesn’t necessarily mean he wants to talk to you above-ground.

It seems he has had multiple chances to speak with you, but never mentioned getting together or exchanging information. It could be shyness, but I think more likely it’s a classic Metro Romance.

May 10, 2006

Step on his neck

Overwhelmed writes,

Breaking up with someone is really hard to do. I want to breakup up with my boyfriend of 1 year. Not because he’s a jerk or has done anything wrong. We have lots of fun and great times together. I just don’t think he and I are compatible when it comes to the long haul of “marriage”. I do love him very much but I’d rather end this than get any deeper than I already am. I don’t believe in trying to change anyone… especially where a guy is concerned. He is wonderful and deserves to be with someone who wants him as he is.

These days I find myself feeling very guilty around him and behaving distant. I”ve made myself less available and have even cancelled a few dates with him. I’ve instigated petty arguments in order to help detach myself from him. I am aware that I’m not being nice but I feel so overwhelmed. A part of me feels cowardly and just wants to behave like a total bitch so he gets fed up and dumps me instead of me having to do the dirty deed. But that could really prolong the breakup and make it a very slow dump. Then there’s that part of me that doesn’t want to be in a relationship with him, yet wants him to still like me. I know this all sounds very selfish. I’m very torn as to how to do this. I dislike confrontation and I hate having to hurt a person I care about. I feel like a weasel. What’s the kindest way to go about this?

Kathryn says,

Maybe forward him this email?

First off, you absolutely have to break up with him - you’re picking fights, cancelling plans, and generally acting distant. I guarantee he knows something is up, but is probably hoping it’s a standard relationship “down” period. But the truth is, you are wasting his time and disrespecting him and your relationship. The longer you let this go on, the less he’s going to like you when you finally do end it.

The kindest thing you can do is honestly tell him, as soon as possible, exactly what you say above. That you’ve come to the tough decision that you and he “are not compatible for the long haul” and that he’s wonderful and hasn’t “done anything wrong.” Tell him you “hate having to hurt a person [you] care about,” and your behavior of late makes you “feel like a weasel.” Be kind, but firm. Reassure him that you had “lots of fun and great times together,” but that they have to end. Tell him you hope you can still be friends some day, but that you’ll give him space, and he can contact you when/if he feels ready. Then leave him alone.

Keep in mind that the meanest thing you can do is string him along. In Shopgirl, Mirabelle says, “I guess I can hurt now, or hurt later. I choose now.” It’s the smartest choice in the long run.

DCB says,

Do you realize that your first paragraph is a great script to dump him with? Stop being a wuss and dump him asap. He is losing valuable time that could be better spent finding your hotter replacement.

May 9, 2006

Not getting hard to get

wherestheline writes,

The problem I’ve always had is figuring out where the line is between playing an appropriate amount of hard-to-get/coming on too strong/and not coming on strong enough so you end up in the friend zone. Are there any general guidelines here?

I’ve heard some people say the girl should never have any doubt that you’re not just trying to be her friend, but then I’ve also heard you should keep from showing your cards until the last minute and never call her more than absolutely necessary at the beginning. It seems like people who advocate this “I’m going to pretend I don’t really like you longer than you” game of chicken all for the sake of gaining the invisible upper-hand might miss out on some great relationships because they overdo the “I’m not interested” thing while trying to look unavailable and thus theoretically more desirable. Are there any general rules here or is it a case-by-case basis kind of thing?

Kathryn says,

The Game sucks. However, having *some* game is extremely important. The musts, generally speaking:

1. When you meet a girl you find interesting, go ahead and ask for her number. Don’t wait for multiple meetings to go by before you get the guts to express interest. That’s how you fall in the friend zone. Trust me, the girl will walk away thinking, “I thought we hit it off, but he left without getting my number. Oh well. On to the next!”

2. Don’t call multiple times before she calls you back. This implies over-eagerness and makes you less desirable.

3. Keep phone calls at the beginning relatively short. OK: chatting for twenty minutes, including setting up a date. Not OK: talking for four hours, staying up all night on a weeknight. Don’t you both have anything better to do?

Everything else should be case-by-case. Numbers 2 and 3 can be phased out as the relationship progresses. Hope that helps.

DCB says,

The big problem with guys is that they are always trying to classify the relationship. Either we’re dating, or we’re in the friends zone, or we’re in a serious relationship. Instead of focusing on where you may or may not be, focus instead on where you want to go and what it takes to get there. At a friends party and spot a girl you like? Get introduced and have an interesting conversation with her. On a first date and trying to get laid? Buy more alcohol and escalate to sex.

There are no general guidelines when it comes to knowing how much game to play because it will always change based on the situation. For example, if you ask a girl out on a date, she declines, and you push like a beta and call back a few hours later, should you be surprised if she will be busy for eternity?

If you are ever confused with how to proceed, simply ask yourself one question: Is what I’m doing now going to put me closer into her pants? If not, then don’t do it. Sometimes it means making a call, and sometimes it means not making the call. Sometimes it means acting like a gentle puppy dog, and sometimes it means taking no prisoners. It depends. You have to experiment with the best way to react in common situations you will face with women. The best answer will come after practice. You’re already thinking about it logically so I’m confident you are on the right path.

Pick Up Artist Mindset new site

May 8, 2006

Fake boobs

To fake or not to fake, that is the question writes,

Here’s an interesting one for you: OK, so I’m a petite girl who grew up extremely flat chested, and though I never necessarily lacked for girl friends or male attention I was always ALWAYS aware of it and self-conscious about it. Right after I graduated college I went and did something about it — got modest breast implants (I wasn’t even an A, now I’m a 34C). I only told a few close college friends (who were very supportive) and then moved to a different city where I made a bunch of new friends. I’ve gained about 10 pounds since college, so of the maybe twice since I got them that an ‘uninformed’ college friend has made an offhand comment, I’ve blamed it on the weight gain and birth control pill hormones (which COULD be possible for all they know!).

Because they are so subtle on my frame (truly!), and I’m not the stereotypical ‘breast implant type’ of girl, none of my new friends has ever suspected. I’m quite comfortable with my intelligent, quirky indie chick (and therefore not ‘breast implant type’ chick) status and the majority of my friends are similarly inclined. I don’t regret getting the implants and I really love filling out my clothes better than before, but I don’t flaunt them and I obviously don’t advertise it. I just don’t think everybody needs to know!

I usually make it a point to hook up with guys who are outside of my friend circle because I don’t want to take the chance of being ‘outed’ to my friends somehow. None of these post-college relationships have been long-term enough to make my breasts a serious topic of discussion between me and the guy and most have either naively not noticed (and just think I have a awesome perky breasts) or, if they suspected, have not, at least to my knowledge, ever gotten word back to any of my new friends.

The problem now is that things are starting to heat up a bit between me and a close friend of some friends, and could potentially lead to more than just short-term drunken fondling. So far it hasn’t progressed passed the making out stage, but I’m definitely interested in more, and opportunities for this may arise sooner rather than later. So, my question is: what do I do about this guy? He’s what you might call an intellectual, and would quite possibly be put off by the thought of a girl with breast implants (I could hope that my personality would sway his opinion otherwise, but who knows?). There’s always a slight chance that he wouldn’t notice, but there’s a better chance that he will.

We are friends, yes, but not the super close-for-years kind where I can just bring it up and explain myself before he, um, notices for himself. And it’s not like some deeply buried secret that I can wait until we are more serious to discuss!

I really like this guy, but do I sabotage my chance with him to maintain my discretion? Should I tell him up front? If you were this guy would you be weirded out by the cute ‘non breast implant type’ girl secretly harboring breast implants after all? If you were this guy would you mention it to your buddies (who would, in turn, possibly mention it to my friends)? Your input would be very helpful! Thanks!

Follow-up:

I just had a thought that you guys might advise me to subtley make a joke about or otherwise bring up implants and see what his reaction is and take my cue from that, but I would imagine that whatever his true feelings, he would say something negative, if just because he thinks that that’s what I would want to hear, being a “non breast implant” type girl and all, so that probably wouldn’t be too productive.

You don’t have to post this follow up, just please don’t advise the above unless you can think of another reason that it may be a viable option. I really think I’ve thought this over from so many possible angles and am at an impasse, hence why I’m after your (wise and) unbiased opinions. There are very few people I can bounce the problem off of since my close friends here that have met him and know the details of our budding relationship are post-college and have no idea about my “secret”. My mom knows but, well, that’s just weird, haha.

Kathryn says,

I don’t see any reason you have to tell him, at least not until he has reason to come into close contact with your enhanced curves. I say, if/when he’s ever feeling you up (sans bra), in between kisses say something like, “I guess you can tell I’ve had a little help here; hope you don’t mind.” Be sure to say this extra breathily. I’m sure he won’t mind at all.

And if for some reason he does think any less of you for having them, I would have to imagine he’s not worth your energy anyway. And if he feels the need to tell his friends in a juvenile, gossipy manner, that goes double.

DCB says,

I’m guessing the point of getting breast implants was so you would have one less thing to worry about. Yet you are still worrying about it!

While it is hard for me to accurately answer your question without seeing a photo of your breasts, I do know that guys don’t really care about implants as long as they aren’t big and gross like those bolt-ons you commonly see in porn.

I disagree with Kathryn about mentioning it in passing. Don’t say anything about it unless he brings it up. And even if he does, stick to the facts: “Yes, I had breast implants years ago.” Don’t make a joke about it, don’t say why you did it, and don’t rationalize it in any way. You made the choice to do this for you so there is no reason to justify it or make yourself uncomfortable for any man. If he can’t handle your breasts then forget him. (If I liked a girl’s chest, it does not matter to me if they are real or not. But I’m an ass man so that’s a moot point.)

May 5, 2006

Guy rather jerk than bang

Given a back seat to porn writes,

This question might be better suited for a psychologist, but I am curious about your opinions on appropriate use of pornography and masturbation while in a committed relationship. One reason why my I ended my last relationship was that I felt we did not have sex enough. We had it about once a week, two at most, and we probably saw each other 3 times a week, staying the night once a week (I wished it was more often, but alas…).

My boyfriend did not seem to have much of a sex drive, especially towards the end of the relationship. He seemed to be most “in the mood” when tipsy or drunk. I gave him positive feedback about his techniques and offered to do “lots of things” for him, but that did not seem to help. He turned me down for sex a few times, even when we went on vacation together, saying he was too tired. Yet he admitted that he masturbated and looked at porn on his computer a few times a week. I felt hurt by this. While I am not against porn or masturbation, isn’t actual sex with someone preferable if you have the option? If a guy is more interested in jacking off to his computer than boinking his (attractive) girlfriend, obviously it is a sign of deeper problems in the relationship, but would you also agree that the guy probably has issues with intimacy and/or commitment? Another thing about this guy was that he was single (and actionless) for a long time (years) before we started going out. I think he got so used to masturbating to porn that he actually prefers it to sex with a woman, although he would never admit this. He is 34 by the way. I’m curious if anyone else has encountered this problem in men.

Kathryn says,

Eesh. For the record, I think that people (not just guys) in sexually healthy relationships still masturbate at least every once in a while. Porn sometimes goes with the territory in those situations. Occasional masturbation is no big deal, assuming everyone is satisfied with the in-person sex.

However, in this situation, he avoided actual sex but still got busy with himself and his porn sites on the regular, and that’s troubling. I would agree it indicates the guy likely has intimacy issues (not necessarily commitment issues; he didn’t cheat on you). Your sleepover pattern - only once a week, despite seeing each other more frequently than that - supports this theory. He liked to have his separate life.

I have no idea why he behaved this way or what caused his intimacy issues, but I can assure you it had nothing to do with you. You seem to have done everything right. In fact, I bet if you were able to call a meeting of his exes, you’d hear the same story from most of them.

Super curious to hear what DCB has to say.

DCB says,

Most guys enjoy a certain niche of porn, such as double-anal, teen blonde whores, messy facials, or cream pies. A certain man likes a specific niche because it is his fantasy, something he wants to do in bed. All you have to do is take a look at the porn he’s watching and duplicate it in the bedroom. Obviously this has its limits if, say, you are a skinny blonde and his porn is all about pregnant brunettes. But in general you can make more of an attempt to branch off from your favorite position - missionary - to try something more fun. My favorite type of porn is dirty latina maids, where a latin woman comes to your house to clean up and ends up having sex with you for money in a series of escalating steps that starts with the removal of her shirt and ends with load on her face.

Kathryn says,

Ew.

May 4, 2006

Diarrhea boy

Ex-lax marks the spot writes,

About 6 months ago, I went out for drinks and ended up going home with a girl I met at the bar. We went down on each other, so no intercourse. I went down on her first, and I could tell that she enjoyed it (Ive been trained by multiple woman how to properly perform oral). She then attempted to return the favor, but after about 3 minutes of the worst blowjob I had ever received, I told her that I had whiskeydick and that it wasn’t going to work. We were both really drunk and tired, so she didn’t get upset or angry at me for stopping her. In fact, I think she was relieved.

In the morning, I said goodbye and took off. She never asked for my number, nor did she look surprised when I left. It appeared that random ass was pretty common for her.

I then started a new consulting project, and ended up at her company’s office. Her company is huge, but I ran into her on my first day there….b/c she was part of my project team. Ouch.

Things went fine, we laughed about knowing each other, and got along ok. We never hooked up again, partly b/c we worked together. She did make a pass at me my last day there, but I acted as if I didn’t pick up on it.

Anyway, after I left that project, I heard the company gossip that she had told everyone in the office (and all my consultant co-workers) that I was the worst lay she ever had. I should mention that she told everyone my FIRST DAY on the job….

Let me reiterate that we didn’t have sex, nor came close to it. I have a burning desire to:

1. Call her up and get us both wasted at some bar (not hard)
2. Go back to her place (not hard, either)
3. Start having sex
4. Abruptly stop, stand-up, and poop on her bed
5. Tell her that she can now truthfully tell people that I was the worst lay she ever had
6. Jump off the bed, grab my clothes and run out of her place completely butt naked.

Should i seek out therapy, or get a box of ex-lax?

DCB says,

Looks like she took a pre-emptive strike against you because she feared you would blab about her horrible bedroom technique. And it worked! Look on the bright side: at least people believe that you are having sex. She can make fun of you all she wants but she admitted that you were good enough to take home and bang on the same night. She made herself look bitter and petty, qualities that I’m sure other people have picked up on.

Wanting to get revenge is completely normal, but I think you already know that this girl isn’t worth any more of your energy. Walk away from this mess with the satisfaction that she is so insecure about her ability to please and keep men that she has to lie to other hens. I don’t think you realize it but you already won.

Kathryn says,

You did win. Not only did this woman fear you would tell the truth - that you are way more skilled than she is - but she let that fear drive her to completely embarrass herself. Think about it - she told COWORKERS you guys had sex, and that you were lousy. This tells her coworkers:

1. She is dumb and loose enough to talk about sex at work.
2. She is dumb and loose enough to have sex with a person she just met, despite supposedly not enjoying his technique.
3. She is dumb and loose enough to talk about a one-night stand with a professional contact (you) with his coworkers.

In summary, she = dumb and loose; you = already off that project and on to better things. Don’t bring Ex-Lax into the equation.

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