How best to proceed from here?

[gay4ass]

So it has been a while since I got back into the dating game. Ended a marriage recently and at 31, now I feel ready to play the fields again. I have always worked out and looked good.

Anyway, I am in a situation now with a girl who is 24 whom I am really curious about. A fellow colleague from my big sized organisation who seems to be likely introverted but with an air of independence which I am so curious about. That and of course she looks good enough for me to want to get into her pants.

I took notice of her and smiled at her one day while passing her. She reciprocated probably as a friendly gesture but unfortunately, due to me rushing for a meeting, I was unable to spare time to approach her. Anyway, I did find out who she is and messaged her on the office IM later in the same day (some might find this a bad idea akin to cold calling a client but hey, I don't care... Nothing to lose for me). Said hello in chat and that I have finally put a name to the face that i am so curious about. A bit of chit chat ensued with me trying to find out about her to strategise my next moves.

The following day, I got on IM again and tried very mild flirting, nothing sexual, just making it obvious that I am curious and added a couple of positive comments about her attractiveness. Told her that I will be lifting her handphone number from the staff directory (not sure if its a wise move...wanted to be as bold and proactive and not waste time in securing a date) and asked if she has any violent objections, to which she said she's fine with.

Chit chat a wee bit more and she asked me about my weekend plans to which I told her honestly what they were (I have friends and dont spend my weekends jerking off in front of the computer) and cheekily added that of course, the weekend will be more ideal if I can sneak in a date with her. To this, she failed to respond. ( red flag)

I am keen to get her out since there is no way for me to gauge if she is interested in the chase if I do not know her enough. I needed to see her in person to do so. So the next day, in the evening while I was with a friend of mine, I texted her "my friend is boring the hell out of me with his incessant rants. help me out a bit.". She did not respond (ego bruised). A this point, I am wondering if I have blown this. Since I have nothing to lose, I do wish to try my luck a bit further and here is where you guys can advise on the next best course of action. I have thought of the following options:

a) Play it cool for a couple of days and text/call her again to try to set a date. However, I am not sure if this looks needy and will it be weird to call her given that we have not officially talked in person. I am thick-skinned and aggressive with such things but there is no point in looking despo/psycho.

b) Just stop all contact and wait till i get a chance to see her in person and re approach her then. The only draw-back of this is that we work in opposite sides of the organisation and it might be a month or more before we bump into each other again.

Like I said earlier. She is interesting enough for me to want to try my luck again. So guys, shoot forth your recommendations and comments please.

 

[sharkbeat]

I don't claim to be the best DJ, but here's my analysis. Take it with a grain of salt.

The following day, I got on IM again and tried very mild flirting, nothing sexual, just making it obvious that I am curious and added a couple of positive comments about her attractiveness.

Don't compliment her unless she actually deserved it. A lot of good-looking chicks get compliments left and right, and you complimenting her does not set you apart from the rest of those chumps, especially if you have just met her.

Told her that I will be lifting her handphone number from the staff directory (not sure if its a wise move...wanted to be as bold and proactive and not waste time in securing a date) and asked if she has any violent objections, to which she said she's fine with.

Why didn't you just ask her directly? Think about it. If you were the woman, and somebody was obviously coming at you, but instead of asking you directly, he said "Can I look up your phone number from the directory?" Would you object? No, since it's public info. But would you find it creepy? Yes.

What would you respond to that? "Err..sure?"

Chit chat a wee bit more and she asked me about my weekend plans to which I told her honestly what they were (I have friends and dont spend my weekends jerking off in front of the computer)

Did you literally say this???

and cheekily added that of course, the weekend will be more ideal if I can sneak in a date with her. To this, she failed to respond. ( red flag)

By saying this, you are demonstrating that she's valuable to you. Having your weekend be more ideal with her implies that she is that much valuable to you. Women tend to run away from this..Read the DJ bible or bradd80's guide especially the part that you should not seek happiness from women.

So the next day, in the evening while I was with a friend of mine, I texted her "my friend is boring the hell out of me with his incessant rants. help me out a bit.".

Women don't play save a bro. We do that. We sweep the women off their feet, not the other way around. When you hang out with friends, thoroughly enjoy their company, and you should not miss a single moment hanging out with them. Don't text her to "save you". Tell her "to come over".

a) Play it cool for a couple of days and text/call her again to try to set a date. However, I am not sure if this looks needy and will it be weird to call her given that we have not officially talked in person. I am thick-skinned and aggressive with such things but there is no point in looking despo/psycho.

b) Just stop all contact and wait till i get a chance to see her in person and re approach her then. The only draw-back of this is that we work in opposite sides of the organisation and it might be a month or more before we bump into each other again.

Go with Option B. Ugh, how about you try to chat her up in person first. No more texts or calls or IMs. You guys are colleagues, right? Why don't you walk up to her cubicle and start a convo? Instead of waiting to bump each other, find some BS reason to go there (like "oh I was talking to HR", whatever).

It's a bit hard at this point since you have obviously played too many cards all at once. She has you figured out that you are into her, and she'll be more defensive. Limited contacts (in person only). Then after a month or two, slowly ask her for coffee breaks, then lunch, then re-escalate.

In the meantime, spin more plates.

 

[Purefilth]

So added that of course, the weekend will be more ideal if I can sneak in a date with her. To this, she failed to respond. ( red flag)

I am keen to get her out since there is no way for me to gauge if she is interested in the chase if I do not know her enough..

bold bit - theres your interest level right there. ZERO.

Also, Im not sure using office IM is wise here - they save transcripts, right?

If she takes offense and makes a complaint, text messages dont convey tone and such things, so they can easily be misinterpreted/ twisted.
So, umm yeah, theres that...



Personally, I would reccommend interactions with women be in person, and without the shield that monitor and keyboard provide.

I dont think she's interested buddy, but you do whatcha wanna do. Its just my thoughts.

 

[gay4ass]

Did you literally say this???

Nah. I did not say this. Just a comment to you guys.


As to why I am not talking to her in person is that our offices are sited at different locations. It will probably be the next corporate event of something before a meeting is likely.

Anyway yeah. Probably time to move on. Just too back I kinda ****ed this up... oh well... time to sharpen those chops again... let this me a lesson to me...