First Date DC

“but seriously, when should i call?”



Hot for Exec. Assistant

Stoopid Monkey writes,

Dear FDDC,

I’ve been hanging out with the executive assistant at my office pretty regularly since she got rehired. During her first stint working at the company, we barely spoke. At present time theres been about 70% turn over at the office and I’m one of the few people left that smokes.

Our smoke breaks went from the usula chit-chat into more personal stuff; like how abusive our single-mothers were/are. We talk about failed relationships and the desire to go back to those people even though it’s nothing but drama. We have the same goofy sense of humor, etc. She talks about the guys she fucks and I talk about the women I bang.

Over the past couple of months, she was having car trouble and I would give her rides home every night. We’d sit and talk or go grab dinner. Essentially, we were spending way too much time together to be just “co-workers”. I have developed feelings for her. I just wanted to fuck her in the beginning, but the more we talk the more I want to have a relationship with her. However, since her last relationship about three months ago she’s gone all whorish with banging her male roommates. She cries on my shoulder about how she’s not like that and how she misses her ex and blah blah blah.

I know she’s not really ready to be in any kind of relationship. And I’m probably not either. She’s ADHD and I’m Bi-Polar with severe depression. It is the blind leading the blind. Everyone in the office can see that I’m infatuated, in a crush, love. . .whatever. And she’s very perceptive about a man’s level of attraction to her. Everyone in the office keeps asking me what the deal is. I’m a consultant so there are lots of demands on my time as well as hers, yet we both drop everything for the other instantly. People know to go through her if they want to get something from me and vice versa.

We always have a great time together and it’s getting to the point where neither one of us wants to hear about the other’s sex-life. I find myself making booty-calls to other girls just to spite her obliviousness to my clear infatuation. I’m trying to separate from her because my level of frustration is so high, but she’s always in my head.

Like I said, neither one of us is really in a place that makes a relationship viable. She’s fighting for custody of her son. I’m suing a stalker (defamation and whole other can of worms) and taking care of my sick mother. We’re there for each other trying to offer sound advice and assistance whenever possible. Any little thing that weighs on me, she wants to be part of the solution or help me deal, and I do the same for her.

Now, all I want to do when I see her is jump her bones and confess my “whatever” to her. If she turns me away I’ll be devastated and I’m sure it will kill whatever this relationship is. If I do nothing, I’m stuck in a place I don’t want to be anymore(the “friend zone”).

Which path do I take? Confess or just walk away. I awit your sage and thoughtful replies.

Stoopid Monkey

DCB says,

Let’s review the reality of this situation:

1. She is clinically crazy. Well, as close as you can get to crazy without being called that by a doctor.

2. She has a kid.

3. She is your coworker.

Bro, can I have some of the crack you are on? This girl has BAD NEWS written all over her slutty face. I know this is a fun fantasy but nothing good can come of it (except for the notch of course). Run away while you still can. But whatever you do, do not confess your feelings to her. That will always be the worst option any man can do to a woman he’s in the friends zone with. It works in the movies, but not in real life. IT NEVER HAS.

Kathryn says,

It’s times like these I’m glad there are handy cliches to fall back on.

Don’t dip your pen in the company ink.

Don’t shit where you eat.

Don’t fuck crazy chicks.

I might have made that last one up, or paraphrased something DCB once wrote.

Can you leave your job and get a new one? Then block her phone number, email, IM, everything? Because honestly, man, not even I can find the slightest positive thing in your entire relationship. She’s using you for emotional support, you both have mental problems best resolved in a therapist’s office and not in a relationship, you are torturing yourself over her actions, and most importantly… you’re making a fool of yourself at work. You said everyone knows you guys are personally involved, to the point that you drop what you’re doing to attend to her personal needs. People go to her to get what they need from you. NONE OF THIS IS GOOD. They clearly aren’t afraid to fire people at your office. Please leave before they fire you.

Time to start over while you still can.

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13 Comments »

whoa… that situation is real complicated. it’s got my head spinning like a top mid-way through the story…

Comment by nabeel on 04/21/06.



Can this be for real?

Comment by Sweet on 04/21/06.



If this question if for real then it makes me really sad.

I believe there is some good possible when two broken people “find” each other, however, neither person seems to be in a place where they can even help themselves, let alone another really fucked up person. Add the work stuff to it and there is no way it could work. And that’s sad because usually the people who are totally incapable of being in a healthy relationship would benefit the most from it.

I need a drink.

Comment by V on 04/21/06.



Do. NOT. Tap. That.
That way there be dragon ladies.

Look, you have what may be your first female friend. Good for you. But if you two get together you’ll lose that and there will likely be a legion of other bad things that would make even Job think you have a hard life.
What you do is you keep her as a friend, she cries on your shoulder and you on hers, but you screw other people. Women do it all the time. They have one guy to talk to, one guy to party with, and one just to screw.
This may be a new experience for you, but you can deal. No touchy the boobies.

Comment by Ibid on 04/21/06.



Whoa. Sounds incredibly complicated, unhealthy and high maintenance. If you like her as a person and would like to maintain a lasting relationship with her, forget about banging her. Go find other girls to do that with. Just keep this one as a platonic friend if you feel she is that important to you and don’t want to risk completely losing your relationship with her. In the meantime, you might want to limit your contact with her in order to distance yourself emotionally. Good Luck with all that.

Comment by Jada on 04/21/06.



I hope she wins the custody battle and moves her son into the house she lives in with a bunch of dudes she’s banging. Because that sounds like a really healthy environment for a little kid to grow up in.

Comment by The Party Girl on 04/21/06.



ADHD isn’t leprosy. ADHD kids need lovin too!

Comment by Anonymous on 04/21/06.



You’re a fucking idiot. You obviously are attracted to the drama of this whole situation, because your question reveals you already know how completely disastrous this would be. You sound like the kind of person who secretly enjoys this kind of sick, doomed love, disaster situations.

The reality is you need medication and therapy. This chick probably need the same. Do not sleep with her.

Comment by Anonymous on 04/21/06.



Dude, you are getting other girls, can’t you be happy with that? Wanting someone this messed up, and who is a coworker with a kid even, should only be the desire of a lamo who never gets any ass and falls for the first woman to smile at him (or cry on his shoulder). You’re getting other ass? Enjoy that ass. Leave this one alone.

Comment by Chaco on 04/21/06.



Wow, lawsuits, bi-polar disorders, children, sick mothers, whorish rommate banging… this has all the makings of an episode of Melrose Place. Put down the melodrama and slowly walk away.

Comment by rock creek rambler on 04/21/06.



This is clearly made up…the Ivy league strikes again.

Comment by Yut on 04/21/06.



Ithinn you should listen to everyones advice here, walk away, find other activities and forgoet about this one. Sounds like you have way too many things to deal with for yourself, you don’t want anymore baggage. Good luck.

Comment by la-la-la-la-lola on 04/21/06.



Really.. don’t worry about trying to take this relationship to the next level because what you have isn’t really a relationship. Don’t upset the status quo of what you already have. Just enjoy sex with other people. Maybe when you both grow up the relationship will develop then. Yeah right.

Comment by Shelovestolaugh on 04/22/06.



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