Can't ask a woman out at work

[gmat]

To begin with, I already know what I need to do, but I just need a push to motivate myself. I work with this woman that I have been talking to on a steady basis since the new year and I know she likes me and she makes me smile every time I see her. I have had long term relationships over the past 10-15 years and have intentionally been alone to deal with some demons I have. I have finally put the past behind me and am ready to move on. There are two problems with the woman I work with:
1) I am 10 years older than her, which IMO is not that large of a gap, we are both adults and we have a lot in common, I think we can work through this
2) This is the real problem, I am senior management where I work and while she doesn’t report directly to me, I technically her boss on some level, and the problem I have is I cannot ask her out during work because it would be inappropriate.
So what do some of you think? Any advice would be greatly appreciated.
Thanks

[Bulldogcakes]

You're overthinking this. Ask her out, do something fun and get to know her. And don't take the dates as seriously as you are the 'asking out' part. You'll be a lousy date if you do.

If you take my advice, do yourself a favor and re-read this thread in a month. I bet you'll be amazed at how complicated you were making things.

[Tallman388]

Since you can't ask her out at work, just make sure you're going to be somewhere where she'll be. If there's some sort of happy hour type event that you both will attend, make sure you go, hang out with her for a while, show her you're not a creep and then set something up outside of this sort of environment. It always worked for me. That way you take work out of the equation, for the most part. Worst case scenario, she says no.

[mdr55]

Go out to to get something to eat or a cup of coffee or something and see where it goes from there. You seem to be too wraped up with what other people in the company might think.......unless there's a policy angainst it.

[donnie_darko]

step one, talk to HR and specifically have them define their stance of fraternizing

step two, DO NOT DATE ANYONE YOU WORK WITH.

step three, ignore those two steps, and possibly get fired or make your work environment extremely uncomfortable.

or step four, you start a wonderful relationship with the occasional fuck in the janitors closet, and enjoy the rest of your life.

though i'm sure the steps set up in step three are more likely.

[Snoogans]

didnt notice it was the forum

[gmat]

didnt notice it was the forum


Don't worry about it. I saw you post and it made me laugh.

[sailor]

recipe for disaster. just a bad, bad idea.

[Justice4all]

To begin with, I already know what I need to do, but I just need a push to motivate myself. I work with this woman that I have been talking to on a steady basis since the new year and I know she likes me and she makes me smile every time I see her. I have had long term relationships over the past 10-15 years and have intentionally been alone to deal with some demons I have. I have finally put the past behind me and am ready to move on. There are two problems with the woman I work with:
1) A)I am 10 years older than her, which IMO is not that large of a gap, we are both adults and we have a lot in common, I think we can work through this
2) B)This is the real problem, I am senior management where I work and while she doesn’t report directly to me, I technically her boss on some level, and the problem I have is I cannot ask her out during work because it would be inappropriate.
So what do some of you think? Any advice would be greatly appreciated.
Thanks

A) The age does not matter. My brother is dating someone 10 years his junior and he is about to ask her to marry him. They are great together and she is perfect for him. So do not worry about that. I have seen some women who are 35 and act like a 15 year old, whereas I have seen a woman at 26 act more mature then many others older then her.

B) Ask her to join you for an after-work drink. Nothing harmful...just a way to 'de-stress' after the workday. Grab a brew, just sit and bullshit. Anything to get her out of the work enviornment. Once you are at the bar/restaurant/whatever....then approach the subject (albiet carefully) about maybe grabbing a movie or something simple....see what her reaction is. If it comes across as positive then you know the next step. I think if you really like this girl and respect both your situations you can make this work.



I wish you alot of luck...go for it! Nothing ventured...nothing gained.

[JPMNICK]

recipe for disaster. just a bad, bad idea.

i agree 100%. this can only end bad.

[hexy68]

dating co-workers present many potential problems...there's a reason HR discourages it

[Soupy_Dreck]

Since you can't ask her out at work, just make sure you're going to be somewhere where she'll be. If there's some sort of happy hour type event that you both will attend, make sure you go, hang out with her for a while, show her you're not a creep and then set something up outside of this sort of environment. It always worked for me. That way you take work out of the equation, for the most part. Worst case scenario, she says no.

i agree with tallman, set up a happy hour for a bunch of work people and invite her. when you're out at the bar, talk to her like you have been and see where it goes. the worst thing is you don't get her but she may be really cool to hang with and she might hook you up with a single friend...

[Furtherman]

Don't shit where you eat.


Seriously... look elsewhere. Just because you see her everyday and you think you're happier for it will look ass backwards on the day it screws up. Ask anyone who's dated at work, it's just not worth it. Now, if she worked in a different department, I'd even say no to that, but that's a least a maybe. But in some way, you're her boss? Dude... smack yourself and look elsewhere.

[ChrisTheCop]

DATING someone at work is no problem.

The problem comes when you break up. IMHO, I'd say look elsewhere, but then again I've rarely been able to. lol. The penis wants what the penis wants.

[ralphbxny]

Get a new job or get her fired and your good too go!

Tell me your 25 and this chick is 15 and I will love this story even more!

[gmat]

Thank you everybody for your advice. Couple of things that were brought up. There is no HR policy against dating co-workers. We actually have a couple of couples that are married. As long as the person doesn’t report directly to you it’s fine. If we do go out and it doesn’t work out, we don’t actually work for the same department so we can avoid one another. She is actually 24 not 15 (and you are right that would be so much cooler).
Anyway we did go out after work today and had a couple of drinks. We both had a very good time and I am sure we will see each other again. She even blew off something else to go out with me, so it looks good. Basically as I said in my original post, I knew what I was going to do, I just needed to motivate myself and get some other opinions other than my stupid friends’.
Once again thanks everybody, I will keep you posted on how it works out.

[Nothing Sound]

1) I am 10 years older than her, which IMO is not that large of a gap, we are both adults and we have a lot in common, I think we can work through this


I am 17 years older than my girlfriend.
I've never gotten along better with anyone in my life.

Go for it.

[LatinSpiceXoX]

quit ur job

[Kris10]

Tough situation. I won't date anyone I work with because of what Chris the Cop said, I don't want to see them when we break up. Thats looking at the glass half full for ya huh? lol