Dastardly Fox writes:
There is a super hot blonde (hands down 10 and never uses makeup) here at my firm, we’ve had several exchanges and she acts like a school girl and gets nervous when we talk (good nervous, clearly attracted to me) and I’m looking for good ways that would let me lead this outside the office for the next stage.  One catch it’s a law firm so I need to keep the office Convo light and fun (don’t Need harassment on my resume)

Oh and I’m not worried about a workplace romance going sour, she’s extremely shy (very smart book work lawyer) im discrete and the firm is huge, so we hardly run into each other and even work on the same floor.  My boy in the kitchen tells me that I’m hot shit because the women talk about me, and I’m attractive so no issues here, its all in the delivery and reason I think. the only catch is that I’m going to have to go out of my way to initiate this, or wait till the next hall encounter… Ideas? Email, phone call, wait for our next hall chat, or walk to her office and just ask? I don’t normally date at work so this is new, but she is by far the finest woman I’ve seen since the last fine woman I saw.

Okay, so when it comes to picking up women at the office/workplace, here are some of Thundercat’s tips…

First of all, try and not present yourself as a “co-worker.”  Being a “co-worker” can scare off women from dating you.  You need to come off as being an “outsider.”  Someone who just happens to work at the same place.  So talking about stuff that doesn’t involve work is a must!

Second, organize out-of-office events that get people to hang out with you in a non-work setting.  In Fox’s case, he could organize a meeting at a nearby bar or restaurant after work, and invite the girl he likes to join him there.  And since there is a group of co-workers meeting, it doesn’t feel like a high-intensity date-type-thingie.

Third, connect with her as much as possible.  Friend her on Facebook, text her if you have her number, email with her, IM, etc.  Do anything possible to chat her up when you’re not in direct contact with her.  This allows you to do all the attraction building stuff you need to.

Fourth, get her to meet you outside the office/workplace where it’s just the two of you.  Grabbing dinner, drinks, whatever.

Finally, be prepared for any objections she may have to dating a co-worker.  Try and anticipate what problems she might have and come up with responses to them BEFORE they arise.

Most people spend like 70% of their day at work, so its natural to want to date out of the workplace.  Just be prepared to handle the consequences if things don’t turn out well!  I personally think it’s worth the risk, but just realize that if a woman isn’t interested, it’s probably not a good idea to pursue it like you would with a woman you don’t work with.

I think every man out there is well aware of all the problems that go with picking women up at work.  As if sexual harrassment wasn’t enough, you now have "sexual intimidation" going on.  (Whatever the hell THAT means!)

Having worked in an office environment myself, I definitely know the plight of many men out there who work 40+ hours a week at their jobs.  So many guys spend so much time at work, and by the time they get home they’re too tired to go out or they need to get MORE work done, so it becomes a real issue of:  work is the only logical place to meet people.

That said, workplace romances aren’t uncommon.  Lots of couples meet through work.  The very fact that two people are working at the same place creates a commonality that can help build rapport and open an avenue to attraction.

Back when I was in an office, one of my office-mates was well known as the "Office Dater."  He’d basically only date women who worked at the company, and he was very good at it.  I’ll share the tips I learned from him to effectively date at the workplace…

1.  Be friendly.  SUPER friendly.  This guy was always incredibly nice
to everyone – especially the women.  He’d greet every woman he saw in
the hallway, he’d always ask people if they needed help with anything
or if he could do anything to make their jobs easier.  The key here is
no matter if you’re attracted to the woman or not, you be friendly to
them, because often times in the office, older women have daughters or
younger friends they just  love to play matchmaker with!

2.  Be interested in them.  My friend would always ask about their
lives outside of work.  How their kids were doing, how their parents
were, if they were any closer to that new car they want, or where they
were planning to go on vacation.  He would just be really fascinated
with what their lives were like, and he would encourage their passions
("You should totally take an art class, you’re gifted!" etc.).

3.  Have interesting stuff to talk about.  One of the things my friend
always did when he got into the office in the morning was check the
news and see if there were any "odd" news stories out there.  Then he’d
walk up to people and bring it up in conversation.  Like "Did you hear
about this woman who gave birth to 8 kids at once?"  Stuff like that.
It always engaged the people he was talking to.  So he could join
anyone at the cafeteria and start talking about something interesting
right away (looking back on it, it was like he instinctively would
create routines based on these stories he could join sets with.  It was
pretty impressive.)

4.  Having a life outside the office.  My friend was in a band, and
he’d occasionally play little gigs around town.  So he’d invite people
(especially women) from the office to check him out.  And if he wasn’t
playing, he’d know of a great local band he’d invite people to check
out with him.  His passion was music, and he’d get women who enjoyed
music as well to go with him to these events.

And this is where he REALLY shined.  By getting them out of the office
"innocently," he was able to work his magic on them without fear of
causing any problems at work.  There’s a different vibe when you’re out
in a social setting with someone than when you’re with them at work.
Usually, by the time he got the woman to go out with him, she already
knew him as the friendly, interesting guy from work.  So she had a
level of comfort with him, and he just worked on making his move and
would usually hook up with the girl that night.

I think its important to remember that most women who work full time
have just as much of a social life as men who work full time, and a guy
who has a passion outside of work, and who does interesting stuff
outside of work, is very attractive and fun.

5.  Remain Friends, No Matter What.  This is probably the most
important guideline.  My office mate would always remain very friendly
with the girls he dated in the office.  If they broke up, it would be a
friendly break-up.  This was necessary to reduce any inter-office
friction.  So always have an "exit strategy," so to speak, when dating
women in the workplace.

There’s probably more my friend did, but I can’t think of everything
now.  I’d have to sit down and try and remember all the tricks and
gimmicks he had.  I guess overall, the important thing is to not really
act sexual at work, but friendly, and get the women to meet you outside
work so you can run your game on them.  Throw a party and invite people
from the office.  Organize an outting of some sort.  Find a nice happy
hour close to work you can invite people to so they can miss the "rush
hour traffic."  Do whatever you can to entice the girls you like to
meet up with you outside of work.