Could She Be Shy And Just Not Sure About Dating An Older Guy?

[Anthony]

I'm a man who's just a bit confused by a response I got last week when I asked out a very attractive lady. I asked her out and got a "maybe" response.

So what exactly does that mean and how should I proceed if I want to try again with her?

A bit of background...We work for the same employer, and see each other about 2-3 times a week in the hallways. She's quite a bit younger than me probably early-mid twenties (I'm 37).

Anyway, I've had several seminars/meetings which she's been involved with. I always thought she was really cute from the first day I saw her, but I'm sort of shy, so it took me a while to get up the nerve to ask her out.

I went down to her office early last week to pass along some work related information, but didn't have the nerve to ask her out then.

We've talked some at work, mostly about general stuff, just chit- chat.

Had a two day meeting last Thursday/Friday and I made up my mind I was going to ask her out. During the meeting, she sat across the room from me and it seemed like she was flirting with me.

She'd flip her hair, smile at me a lot and place her hands the same way mine were.

There were about 20-25 people at this meeting, so it wasn't too easy to just go talk to her. I did some, just small talk, and finally I decided to ask her out Friday.

I went up to her after the conference was over, and asked her if she was seeing anybody. She said no, so I asked her if she'd like to go out sometime.

Her response was maybe, so I said she knew how to contact me and left.

She has been in meetings Monday/Tuesday, so I thought about trying to maybe contact her Thursday. But I don't want to come across as being pushy or anything like that.

Should I try to contact her first or wait a while and see if she tries to contact me? I figured I'd ask her if she'd like to go for a walk downtown one afternoon on break and/or maybe ask her out to lunch one day.

What's the best way to do this so I don't get the dreaded "no" or another "maybe" answer?

I could find an excuse to go to her office, but there are other people around and it makes me nervous enough when I'm asking somebody out without having other people around listening in.

Would a phone call be a better way of doing this? I've thought about asking some of her co-workers about her since I'm friends with some of them, but I'd rather just ask her myself.

I hope you can give me a quick bit of advice.

The "maybe" answer was one I haven't heard before. I'd almost rather she'd have said no.

Is "maybe" just her way of saying she's not interested without saying no? Or could she also be shy and just not sure about dating an older guy?

From what I've seen of her, I think she might be shy.

[David]

I'll address the most obvious issue first. Since she's a co-worker, I'd avoid dating her altogether because of the potential complexities involved.

The old adage about "dipping one's pen in the company ink" applies here. Basically, the assumption is that your career is too important to sacrifice at the alter of having to deal with someone on the job who you are involved with or (worse) were involved with.

At best it's a distraction for both the two of you AND your other co-workers when things are going well between the two of you.

But should you ever suffer a bitter breakup, not only will work become a nightmare, you may find she sabotages your career either consciously or unconsciously in some petty way.

Let's just tell it like it is. With over three billion women on Earth, you'd do well to find one that doesn't work in the same office as you do.

And for the benefit of others reading, what I've just said goes DOUBLE if whoever you have your eye on is either a subordinate or a client.

All of that said, I fully realize almost none of you reading this are likely to pay any heed to logic.

Surveys still show that "the workplace" is the second most common place for Americans to meet their future spouse.

It's my contention, however, that the whole "pen/ink" factor is pretty much moot in this case.

Sure, it's altogether possible that SHE may be more wary of dating a co-worker than you are. That could indeed be driving this.

Or, perhaps she was looking for more definitive leadership from you after she gave you that tentative answer. Some women really want to see a bold, confident move even in the face of a bit of resistance.

That's rather rare among mature adults, however. And for what it's worth, if that's what was going on then the mood would have had to have been decidedly playful as opposed to cold and direct.

But that aside, my gut feeling is that if she were all that interested in you romantically, she would have made sure the straightforward conversation you started with her about going out sometime would have resulted in firm plans.

That didn't happen.

As such, her giving you "maybe" as an answer comes off as a purely manipulative tactic that puts her in the driver's seat insofar as decision making goes.

She can now take her sweet time to figure out what the relationship between you and her should be.

If she wants, she might even attempt to control you to the end of meeting whatever non-romantic needs she has (job related ones, even? Ouch!) by perpetually "dangling the carrot".

Either way, the bottom line is that despite her flirtation during meetings, she's not enthusiastic about going out on a date with you.

The ideas for follow-up that you've suggested almost never lead to increased attraction on her part, which is really the missing piece of the puzzle.

There's not much of a point to asking co-workers about her since you've already talked to her directly. Such only makes your business everyone else's.

Ultimately, I really would recommend looking elsewhere for someone to go out with.

My general impression is that you don't deserve this sort of "game playing", yet she's been straight-up rude to you.

If you see the world as rife with female possibilities, you will not have such a pronounced need for this particular woman.

The irony is that once that is a reality for you, even women you work with start coming on to you first.

But who needs them, really? You'll have opened up a far broader (and more private) world of new possibilities outside the workplace.

How cool is that?

[Anthony]

Thank you David for your advice.