Should I ask her out?

[zyphfly]

So heres my scenario…

 

There is a business I frequent, and have done some business with myself, so I'm pretty well known there, I'm also friends with the owner. For obvious reasons, I'd prefer not to get too descriptive beyond that.

 

Anyway, there is a girl that works there that I've found attractive for quite a while, but never really had the nerve to talk to her (didn't really have a reason either, as the people I do business with there don't have much to do with her department). As time has progressed though in recent weeks I've started making an effort to talk to her, and have found out some details about her, particularly that she is 6 years younger than me (I'm 29).

 

I don't want to get really long winded here, but in short…the age thing isn't a deterrent to me so much as long as we are enough of an intellectual match, and she's seems pretty intelligent from what I can gather.

 

Here's the part where I'm a little thrown for a loop though, and I'd love to get some opinions.

 

Conversation just doesn't seem to occur very naturally for us. We have talked quite a bit, but it just feels awkward like I have to try really hard to steer the conversation. She is nice to me, she does joke around with me, but I don't know how else to describe it, she just comes across kind of, I don't know…dry, witty, cynical, quirky, etc. Hard to read I guess. I've been told by one of her co-workers that she's very shy, but I don't get that impression when I see the way she interacts with other people.

 

Wishful thinking says that maybe she is just intimated by me and that she is also interested, but is showing it in a strange way. But then the devil on my shoulder tells me that maybe she is only nice to me because she feels she has to be due to the circumstances of the job, and that she probably views me like I'm an old man or something, or maybe to not go there as I'm friends with her boss.

 

I don't even know enough about her to really say with certainty that she is someone I should pursue dating, just that what I do know about her has me crushing badly at the moment. I would really like to ask her out, and I'm pretty sure the owner would be okay with it, but I don't want to make an awkward situation for anyone involved, I don't want to make her uncomfortable at work, I don't want to damage my relationship with the owner (or cause him to lose a good employee), etc. Not to mention, the nature of her job (she is almost always with customers or co-workers, so getting time alone with her is difficult) would make asking her out while at work kind of tricky as well, and before anyone suggests the next obvious step, she has no social media accounts, which both intrigues me, and also forces me to have to go about this the old fashioned way!

 

So, advice time: Am I just over thinking this? I've heard all these "the minute you wonder if she likes you, you've given away all power" speeches, and have tried to adhere to that mindset when asking someone out for the most part, but as this situation is a little more complex I just really don't want to do the wrong thing. Do I just go for it hope for the best, or does the situation seem "off"? I know I've been kind of vague for both the sake of brevity and anonymity, but if you'd like some further details to help assess the situation, I can provide them.

Edited May 2, 2015 by zyphfly

[Satu]

So, advice time: *Am I just over thinking this? I've heard all these "the minute you wonder if she likes you, you've given away all power" speeches, and have tried to adhere to that mindset when asking someone out for the most part, but as this situation is a little more complex I just really don't want to do the wrong thing. Do I just go for it hope for the best, or does the situation seem "off"? I know I've been kind of vague for both the sake of brevity and anonymity, but if you'd like some further details to help assess the situation, I can provide them.

 

*Yes, you are.

 

You either accept some risk and ask her out, or you don't.

[preraph]

Your age gap is nothing. That alone wouldn't stop anything from developing. What is worrisome is things are awkward with her when you talk. If you have chemistry with someone, usually the talk would flow nicely. I see a lot of guys on here more or less hoping the reason a girl isn't reacting right is because they're shy or intimidated, but I have to only speak from my own 62 years of observation and tell you that I've never come across women whose shyness manifested in that way. Maybe they were too shy to approach a man, but never to shy to speak to them. Also, being cynical isn't really the mark of a shy person or an intimidated person. Being cynical is bold.

 

And yes you are right to assume she has to be nice to you because you're doing business.

 

I think all you can do at this point is slowly find out if she is really single or has a boyfriend. Ask her if she has any kids. If she's ever gone for vacation and then you see her after, ask her about her vacation, where she went and with who. Maybe you could invite a group of people from her place of employment to lunch and see how she is doing that. Really, you have to just see if you can get to know her a little because it's hard to tell if she likes you.

 

I will tell one cautionary tale from a place I worked. There was a woman working there who was really beautiful, but she was more or less a hillbilly. She was quiet and had a quiet voice, so she often seemed ladylike, but working there with her, I'd heard her cuss out her baby daddy and act like a real tough chick. But she didn't look that way at all, and all our salesmen who visited walked by her desk and would always ask about her. Because she appeared demure, outward appearances, and big boobs, of course :rolleyes: But the salesmen were convinced she liked them back because she was soft-spoken and demure and they had no clue she had 3 screaming kids and a baby daddy who was a semi-pro wrestler with whom she fought like cats and dogs.

 

So I'm just saying that in a business setting, you may or may not see the real person at all. So you have to wade in slowly and if you have a discreet buddy there, maybe you ask a discreet question or two, but that could backfire. Good luck. Maybe she'll warm up more and things will become more clear as time goes on.