Not sure what to make of this or how to proceed

[Uncertainty]

Hello all, new member here!

And a preemptive sorry for the length of this post for those of you willing to read.

First things first, some back story. Over the last few months I've really taken interest in a woman the works in the same building as I (different employer). I first started chatting her up about a year ago, but toward the beginning I was still involved in a relationship and didn't want to start having feelings for someone else. Anyway, there is some age difference between us (she's 38 and I'll be 31 next month), but aside from that we seem to get along very well and don't show a maturity difference (i.e. she acts young and youthful and myself more mature). Aside from that, this woman has a lot going on - teenage daughter, works until 9:30-7:30 and then drives 45 minutes to get back home at which point she probably has to cook dinner on top of it, so I'm not sure how that plays into this situation.

Anyway, she appears to have some kind of interest in me. For example, she gives a big smile and a wave as I walk by, and has also shared quite a bit of personal information with me (i.e. has talked about her daughter and her daughter's dead-beat dad, her own dysfunctional father, etc.) as well as making and keeping eye contact with me and laughing at my stupid jokes.

I think at some point I may have started to come on a little too strong in certain areas (i.e. finding excuses to talk with her too often) and she started to pull away a little, or more optimistically this could have been her playing hard to get (still confused on that one). An example of this is that she usually stops and chats with me when she goes for coffee (as she passes right by my department), but on one occasion she didn't seem her usual self and said "hi", when I asked her "what's up?" she said "busy day" as she kind of swiveled her body to face me, but never stopped to talk like normal.

Nonetheless, I did say the heck with it and asked her out. For specifics this is what I did/said: Walked by and struck up a conversation with her. I said something along the lines of "It's been a long week, I need a drink". She replied with "If you find one let me know" - in which case I saw a green light (or what I thought was a green light) and said "You should have a drink with me one of these days". Her reply was "maybe" with a smile on her face and said something along the lines of "I thought you didn't drink" in which my reply was "well I drink a couple times a month" and followed up with "well, here's my number if you want that drink. Don't be afraid to call!". After that I went on with our normal conversation for a few moments, excused myself and walked away. Later on in the day, I saw her by the door as I was leaving and talked to her for a good 10 minutes. Nothing seemed strange at all after asking her out. This was about a week or more ago.

This is where it gets sort of weird. The next day I was away from my department and missed her walking through, but sort of caught her on the way back as I had to do some work to the side where I usually talk to her. Trying to be slick, I pretended like I didn't see her and I'm pretty sure she looked up and saw me as I tend to have pretty good peripheral vision. In any event, she went the other way around in which looked like a move to avoiding me. Now to play devil's advocate, she could have had business to take care of the other way, but I never seen her go that way and can't say with any kind of certainty.

After that I didn't acknowledge her at all when I walked by her department, but she did see me in the distance one time after our eyes met - I wasn't even looking for her but she smiled. Figured I should try the "I'm not worried about you because I have other options" routine like the day previous and not test my luck. Head/eyes forward and back to work.

A few days later (as I was off work the day previous), I was again on the side doing my work (similar to the other situation but a little more off to the side and out of view) when she came back through again. I pretended like I was pretty busy said "hi" and "what's up?" and she said "nothing" (not in an unfriendly way though) and kept on her way. The rest of the day I played the "I'm too busy to stop and chat or even look in your direction routine". In fact, at one point I walked through while she was working and could see her look up in my direction in my periphery.

The next day is where it gets even more confusing. As a friend told me I should cease with the cold shoulder treatment and act friendly, but neutral with her. Basically an alpha male type response of "The ship has sailed and I have plenty of options". The idea was to smile, say hi, and interact if she didn't seem uncomfortable at all.

Well, what ended up happening was a complete 180 from before. Not only did she smile, but she put up the big wave and seemed very inviting and friendly. We talked about some sports (she is a big sports fan) and then when the conversation got going nicely, I excused myself and went on my way. I did the same thing later in the day, but cut the conversation even shorter than the last as to illustrate that I have important things to do (when in reality I don't lol). More alpha behavior.

So my question to you is, what do you feel about her behavior (early and present)? Is she doing the classic push/pull or playing hard to get?

What do you feel her "maybe" answer meant and should I ask her out again (more like me demanding that she goes out with me lol)?

In general how should I play this situation?

Again...sorry for the length and thanks for any advice.

[Agape]

I'm not sure but since you're both 30+ you should stop with the push/pull games and be direct with your feelings. . . where do you want to take this friendship?

I think you should ask her again, and if she continues on with the games then leave it.

[MerryH]

Stop trying to be "slick" and an "alpha male." If you really were either of those things, you wouldn't have to be trying to so hard to emulate it. And since you're just pretending, you're probably not pulling it off as well as you think you are. Just be natural. You're playing silly games and overcomplicating this. If you want to talk to her, then do it.

And you don't need to "demand" that she goes out with you. You hardly even asked her out to begin with. Try again, naming a specific time and date, instead of just "one of these days."

[lilefia]

I have to agree with the above posts. Stop acting like your in middle school and take charge of the situation. Clearly she has some interest in you, so ask her out. If she says no, then be cordial with her at work and move on. Enough of the games.

[Uncertainty]

I'm not sure but since you're both 30+ you should stop with the push/pull games and be direct with your feelings. . . where do you want to take this friendship?

I think you should ask her again, and if she continues on with the games then leave it.

It's kind of hard to tell where something is going when the only exposure you have to someone in the work environment, but I will say that I do enjoy talking to her though and want to take it one step further.

Agreed about the games. It was never my intention to play them. I guess I just got caught up in the situation.

Stop trying to be "slick" and an "alpha male." If you really were either of those things, you wouldn't have to be trying to so hard to emulate it. And since you're just pretending, you're probably not pulling it off as well as you think you are. Just be natural. You're playing silly games and overcomplicating this. If you want to talk to her, then do it.

And you don't need to "demand" that she goes out with you. You hardly even asked her out to begin with. Try again, naming a specific time and date, instead of just "one of these days."

The whole alpha male thing was sort of in jest. However, I have had quite a few people tell me that I need to change my approach to this situation (i.e. not overpursuing).

Agreed about asking her out with something specific in mind though. I just worry about trying to set a specific time for a date with her seemingly busy life. But I guess that I have to get over it and just do it.

I have to agree with the above posts. Stop acting like your in middle school and take charge of the situation. Clearly she has some interest in you, so ask her out. If she says no, then be cordial with her at work and move on. Enough of the games.

Yeah, no more games - or at least on my part. Again, agreed about the asking out part. I'm just wondering if should wait a little longer or just go for it?

Thanks for the advice either way (everyone).

[Uncertainty]

Update:

So I decided it was better to have an answer than wonder "what if?" and ended up asking her out Thursday. She mentioned having Friday and Saturday off so I figured one of those two days would be optimal.

Mind you, the day previous (Wednesday) I did her a pretty big favor (job related) so I jokingly said "since you owe me" you should let me take you out for a drink on one of the two days. She said something to the effect of "I'm not going to be up here" (i.e. she lives 45 minutes away from where we work). I said, "well, I'll come to XXXX (name of the city isn't important - but it's about 15 minutes from her). She acknowledged the favor I did for her, but said that she couldn't let me do that (i.e. drive the distance). I said that it was no big deal. After a little more hemming and hawing, I asked her what she was afraid of and she just answered with a "I'm sorry I can't".

At that point, I was just looking for a definite answer one way or another and told her that it was okay to say "no" if she didn't want to go out with me for a drink. She paused for a second and said "Actually...I'm going to Texas to see a guy" (She had mentioned about a week before that she was going to Texas). Anyway, after mentioning Texas she said "...but raincheck" in which I assume she was referring to going out or having a drink.

After that I left well enough alone. Didn't ask anything about the guy in Texas or the relationship itself. I figured that it wasn't my business and didn't want to come off as bitter or jealous. Eventually excused myself and went on my way. I did see her today though (as both of us occasionally work weekends) and everything seemed okay.

Anyway, it was a little tough processing this whole thing.

- First of all, when she was saying "maybe", "I can't", etc., her body language was painting a completely different picture. More like a "yes, yes, and YES". It was almost like she was struggling with turning down my request.

- Second, what the heck is the whole "...but, raincheck" thing all about. Is it that she sees me as an option and is waiting for a little more clarity on "Tex"? Mind you, I don't know if there is history between the two, but Texas is a long distance from Upstate New York where we live.

- Third, I figure in the very least, she has some integrity as she could have easily went out with me for a drink while also playing Tex.

- And forth, this could also be her stringing me along, but I don't think she would do that. However, I can't say for certain. Another thing to mention is that the Texas situation seemed to be in play before I asked her out, so it could be just a timing thing.

So, what do you guys/gals make of this?

[MerryH]

"I'm sorry I can't"

This is a definite answer. It means no. Maybe she said "raincheck" because you made her feel like she owes you a date AND you kept bugging her about it.

Good job for having the balls to ask her, but she said no. Sorry.

[Uncertainty]

This is a definite answer. It means no. Maybe she said "raincheck" because you made her feel like she owes you a date AND you kept bugging her about it.

Good job for having the balls to ask her, but she said no. Sorry.

I still think that was in reference to the Texas situation and it was more of a timing thing than anything else. Like I said though, the body language seemed completely opposite.

Either way, I'll still be friendly with her and I'm sure it'll play itself out if there is anything there.

[Agape]

"I asked her what she was afraid of and she just answered with a "I'm sorry I can't". "
"when she was saying "maybe", "I can't", etc."

She said no . . . if she really wants anything then she'll have to come up to you . . . move on . . . about this guy stuff, that's a pretty good negative indicator as well

[Uncertainty]

I know. It's probably just a way for me to walk away with my confidence in tact.

[MerryH]

You should feel confident and proud that you put yourself out there and gave it a try. Nothing wrong with that.