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How To Date a Cute Girl from Work without Losing your Job

If you ever thought about dating a girl from work, this one is for you If you ever thought about dating a girl from work, this one is for you

53% of men is eyeing up a colleague. That figure includes you.

But a lot of these guys don’t take any action, because lets be frank; we don’t want to embarrass ourselves in front of the whole company.

And you might lose your job. Maybe she might. Maybe you like it the way you can talk friendly to each other right now, and you don’t want any sour feelings between you.

There are 100’s of excuses and fears for not trying. But they don’t get you anywhere.

So let’s get down to business and see how you can approach her with minimum embarrassment and maximum results.

The how-to of dating women at work

  • Get to know her in a casual way. As some wise guy once said, “start by laying the foundations”. This is very important when it comes to dating a work girl. Smoothly start to make small talk with her at the water cooler. Talk to her casually at lunch. Simply make sure that she knows your name and who you are.
  • See her outside of work. Now that she knows who you are and you (may) have some friends in common, what would be more natural than grabbing a beer after work? Take 5-6 colleagues (including her) to a bar one day for a happy hour. Have fun! Be the guy that she would want to be with. Don’t flirt too heavily though, it’s best that she doesn’t know your dark intentions yet. This way there’s no pressure. At the bar, you can play a cute game with her. Remember that entertainment and fun is the most valuable values you can possess. So be fun, and have fun!
  • Be alone with her. This is the natural next step. If you enjoy her company, and she enjoys yours, you should get to know each other better. Don’t go overboard with things just yet, take it easy. Casually ask her what she is doing for lunch one day, or do a project together. Maybe just meet up with her at the coffee machine for a five minute conversation. It’s important that it’s just you and her, as she will most likely start to see you in a slightly new light afterwards. Also, if she has had some dirty thoughts about you, being alone with you confirms to her that there aren’t going to be awkward silence when it’s just you two, which may have held her back. Remember this: It’s not a date. It’s just two co-workers having lunch. Keep it light!
  • Check your progress. When you, her, and a bunch of colleagues are out together, how does she act? Does she keep coming over to you, talking to you, drinking with you, touching you? (Such as placing her hand on your arm, or your shoulder.) If yes, it’s time to go further. If she is interested in you (romantically), you should definitely go for it. If not, you have three options. Number one is to give up. If you and her isn’t going anywhere, this might be a good one. Don’t spend too much time or energy on one girl. Don’t stop talking to her altogether, just cool down a little. Number two is to keep doing what you’re doing. If you’re making slow but steady progress, this is a good idea. Just move things forward slowly. If you’re not, Number 3 is to change your approach. Do something new and different. If what you’re doing doesn’t work, do something else.
  • Ask her out. If everything has been going as it should, asking her out should be easy as cake. You want to get to know her better, and you feel attracted to each other. Go get her tiger!

With this approach, you run (almost) no chances. Until you’re sure that you get positive signs from her, you keep it very fun and friendly.

But when the signs do come, you turn it up a notch. Nothing too heavily, especially not in front of your work mates, but make sure to always more forward. Remember the “Two steps forward, one step back” rule.

Following these simple tips, you shouldn’t have a hard time dating girls from work. The most important things to remember is to keep it fun, keep it light and keep it casual. Make it really natural and flowing, and lay off all pressure so it won’t get awkward.

There are no limitations

No practical post without a little bit of motivational speak…

Remember that “time never waits”. Our bodies change every second. We get older. The world moves on. So don’t be afraid of change!

Give it a chance. Don’t ever disregard anything without giving it a fair shot.

No girl is “out of your league”. Don’t ever worry about what life “would be like”. Try to live and take action instead. Your best is always enough. It’s better than enough.

Good luck soldier!

Field reports from the hard environment of the office is highly encouraged. Have a sweet love story that started at work? Maybe the opposite? Post in the comments!

You never know exactly when I post. So stop spending time checking in and start using RSS. I’ll send you my post by email when I publish something. Promise!

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24 thoughts on “How To Date a Cute Girl from Work without Losing your Job

  1. Blaine Moore

    I never had much desire or inclination to fool around with somebody at work. Risk vs Reward didn’t make it worthwhile when I knew plenty of people outside of work. “Don’t eat where you s***” seemed to make a lot of sense to me.

    That being said, definitely a good strategy to avoid embarrassment (of both yourself and of her) if you are interested in a coworker. Note that this strategy would probably work just as well with a client or a regular customer as with a coworker.

  2. Alex

    Yeah, I guess it would work on most people you see almost on a daily basis Blaine.

    Good point on the bathroom issue… But hey! Some people sit all day at their office, and don’t really have time to go people-hunting after work. I just thought that an article for these guys was appropriate ;)

  3. Robert A. Henru

    Raymond, that’s too bad for you… don’t go for the neighborhood aunties ok! Maybe their cute daughter will be great =)

    For me is about the same, there is not much girl in my office, mostly engineers so mostly guys. got to rely on some other friends

    Alex… thanks for the tips, your last statement is very encouraging! Thank you, commando!

  4. Alex

    Raymond, I see… Always something that there’s a whole world filled with cute girls outside the windows then!

    Robert, lol! Where do you get that stuff from…

    I should make this into a military academy of some sort, could be fun actually.


    I’m not THAT mean! I’m more of a hippie Jack Johnson guitar kind of guy.

    But some military disciple is actually sometimes what you need to get out and do what needs to be done.

  5. Maria - Never the Same River Twice

    One thing I would add to your advice, Alex: Don’t date someone who is in the same hierarchy as you. That means, don’t date someone who reports to you, or someone you report too. At least in the U.S. that is a sure way to get fired and possibly sued.

    Ideally, you should date someone in a different department if you are going to pursue relationships at work.

  6. Alex

    Thanks for the advice Maria! There surely are somethings to keep in mind when dating people from work.

    I don’t mind at all Doug! Nice article :)

  7. Ivy

    The only two times I dated someone I worked with, the first time I moved away and he knew I would so there was no potential danger, second time we both got fired but now we’re getting married after dating for 6 years.

    I know a lot of people in my company who met while working there and are now married and still working for the same company… (in different departments)

  8. Tyler Moss

    I like this article allot. The only thing I might add is that its not that great of an idea to date a woman that you actually work with directly. It could complicate things a great deal for you at work if things got bad in your relationship.

  9. Alex

    Seeee… It can work! :)

    Great to hear Ivy. Nice stories.

    Tyler, appreciated.

    No, it could potentially create some problems (if there was a *break-up* per se)

    Thanks for all your comments!

  10. A.J

    hey alex, i didn’t know where to write this or how to get in touch with you so i figured i’d post here.
    i have a question. I am a waiter and there are some attractive girls that come to the restaurant. how would i approach a girl when im not serving her? How would i get a number? how would i introduce myself, what if she is with her mother. Any input would be great because right now im totally lost.

  11. Alex


    you can always get in touch with me via the about page, where there is a contact form.

    Anyway! Sounds like a great spot to meet women, and a great spot for some good old practice.

    The best thing you can do is to serve her/them. This way it will most likely be easier.

    It will also be easier if she isn’t with her mother, but she doesn’t have to stand in the way. If you play your cards right, she might actually help you.

    When going for the number, be the funny/sexy waiter right from the beginning. You can actually start by introducing yourself. Maybe not by shaking hands, but by saying something like:

    “Ladies, ladies! You sure look beautiful tonight. I’m Charles, and I’ll be your waiter for the evening. *pulls out chairs* Sit down and I’ll bring your menu’s right away”

    Think “italian casanova” type of guy.

    For the number, you could ask her to put it on the note when they pay. Something subtle and fun. You’ll work it out. Hell, if you do well, she’ll ask for yours!

    I think you could get a lot of great ideas if you read David’s book Double Your Dating. There are a lot of good tips that you could use. Here’s the link:

    Double your dating

    You could also read the review first.

    Good luck mate, and let me know if you have more questions!

  12. Suneel

    Well, nice tips. But, I like to let your remind of the extremely inauspicious occasions which I am always a scape goat of.

    No matter which project we are in, there is always a deficiency of these kind of cute girls over whom we can amuse ourselves :(

  13. Jinx

    Dear Alex,

    help me out man!!

    I need some serious help from you. I am 24 year of age just done my graduation and landed up in a cool job with a damn good profile, She is young,very hot and very sexy, she works two tier below me and greatest part is she doesn’t report to me actually her boss is equivalent to my position. We get to talk near water cooler and coffee machine. She works in the floor below me and we never had lunch together.

    One fine day our office had arranged an offical picnic for all. Me and that girl had a good time together. And I asked her out!! ( all of a sudden, I don’t know why? May be I was highly excited and this is my first job ) and she kinda said no in a polite way. Any ways we exchanged numbers and she text me and call me out some times and so do I.

    I know this girl likes me and I like her also, but I am aware now because she rejected my dating proposal although we have taken it cooly.

    When she calls me very often and as about stuffs like How was your day and all.

    What should I do?

    I don’t want to ask her out again? If she said NO it will be all over the place!!!

    And I don’t wana miss any opportunity to miss this chance because she is one of the hottest babe I have ever come across.

    I need sincere help !!


  14. Titoo

    Hey JINX, I say stop talking to her. What kind of girl likes you and wants to know how your day has been, yet doesn’t want to go out? Sounds like she is a waste of time. Find someone who is worth it.

  15. Rich

    I work in a nursery full of girls, I’m pretty sure this one beauty of a girl likes me but what’s the best way to ask her out, I’m abit edgy about everybody finding out and putting her off :s

  16. Don hesson

    Hi,well I met this girl at work she’s really unique,smart ,as well as beautiful.We talk ALOT but I do believe in not dating girls from work for the simple fact things can get complicated.she just got hired. I’m confused and don’t know what to do.DON HESSON

  17. Don hesson

    I’ve made my decision .I will remain strong and professional and not date my co-worker.I’m not that easy.I have a job to maintain and respect.I will not date my sexxy hot new co-worker! God she’s hott!!! Don HESSON.

  18. AP

    Hi Alex,

    There’s a lot of guy asking questions here, so I thought I’d share a little success story with you all.

    My gf of three years left me a litle on three months ago, I was devestated, but I’ve spent the intervening period looking forward – exercising heaps,reading this blog, starting conversations with girls on the street, doing all the things that improve one’s self esteem.

    There’s a SMOKING HOT girl at work who has ALWAYS flirted with me, but because I was with my girlfriend, I couldn’t reciprocate. This girl gave me her number over some BS/innocent pretext about 2 years ago, and becase I was with my girlfriend, I never felt the need to call her. This prticularly girl learned that I was recently single, and when we next chatted, she immediately deemed me her “drinking buddy” (which I think is womaneese for “Im single too. Lets dance”).

    So, I went on a holiday for two weeks to get away from all the crap thats been going on – mental R&R. When I got back, I though “Hey, I got nothing to lose” and decided to text this girl and invite her out for a few drinks with a few mates of mine – just after-work drinks, no biggie.

    She graciously accepted IMMEDIATELY.

    Within an hour of joking about and treating her like a bratty litle sister, I had an invite to a New Years cocktail party out of town. Turns out she had been stalking my Facebook page, knew where I went on holiday, realised I had family there, and *just by coincidence* is going be nearby for Xmas/New Years.

    So, our *innocent* night out ended up with her lipstick all over my shirt. We’ve since had a few more outings outside of work, about once a week, which have all gone really well.
    Ask loads of questions gentlemen, dont reveal too much about yourself, and above all, remember some of the things she tells you and just subtly drop it in a conversation – it shows you were listing.

    Body language, fellas is a dead give away: on all dates, this girl has been playing with hair, maintinaing eye contact, keeps touching my leg or arm, and her body has always been oriented my way. Last week, when we were out with with some work people again, I decided to try a little experiment: I returned from the bathroom and deliberatley sat at another spot at the table – BAM! Her body orientation moved too.

    So, here I am, learning all about this big bad dating world and hell bent not to repeat the mistakes I made with girls in the past. Im not a Don Juan by any means, but thanks to advice I’ve read on this blog, I’m now getting girls’ numbers left right and centre. Most important, Im enjoying this little game I now have with this girl at work, which I’ve decided to pursue outside of work. One thing I’ve learned so far is the value of being a challenge and how important it is creating attraction – it seems to be working for me so far.

    Now that I know this girl is interested, Im going to see what happens if I dont email or message her for a few days. Three steps forward, one step back, and all that.

    I’ll let you guys know how it all pans out.

  19. C.A

    Hi there, I’d like to tell u my current situation.

    Im an unhappily married man, tho im living my life the best I can on my own, Im responsible, I take care of my home financial issues, im a decent father, my kids got everything they need and most of the stuff they want. But in terms of relationships, well lets resume by saying Im definetively not happy.

    I met a gorgeous girl at job, about a year or so, she is working at a diferent city, but we use to have anual meetings, she isn’t that far actually, just about 45 minutes in plane, 6 hours in car.

    I have been interacting with her through phone calls and msgs, mostly work stuff, but recently I’ve feel some sort of closelyness to her, we tend to share some stuff from our personal lifes, she isnt happy with her relation either… in fact her wife went to another country about a year or so.

    Following the 2 steps fordwar 1 step back, sometimes I test her out by not writing or calling, or not answering her calls (I ask the guys at the local office to help me out with the job stuff relating her). And she then calls me to my cellphone asking why i havent even greeted her or said good bye. I must admit sometimes she does the same to me.

    The thing is, this is really complicated, I really like the girl, I havent got the guts to just take a plane and go there. I dont know if I should do this considering my current situation. But Im quite sure I like her and viceversa.

    What would you do?