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I need a lot of help with what i should do next.

Wed. Aug 14. W was supposed to come by in morning to pick up mail. Here is what has happened since.

Text exchange:

Her: got pulled to sf today. Can I come by tonight or tomorrow night? Friday morning might work too.

Me: do you just want to get mail? Do you need car?

Her (8:16 am): Need mail. We can arrange car another day if that is ok with u :-)

Me (8:37 am): Ok. Just let me know when ur coming and if I won't be here, I will leave where you can pick it up.

Me (10:51 am): FYI (phone) bill is due again in a couple of days.. I know it seems like we just paid it

Her (11:56 am): I can pay online now that I ha e login. I will post $xxx payment tonight, k?

Me (12:14 pm): k. Pls let me know balance after you pay. Btw we are eligible for new phones if you want one.

Her: (12:16 pm): I totally need one but don't want to commit to two year contract.

Her (2:55 pm): U working at nights still?

Me (2:59 pm): No summer session just ended. Only doing (job #2) until fall when I have 4 classes.. Yikes!

Her (3:04 pm): Busy guy ... Do you have kids tonight? I could really use a few hrs out getting a drink & appetizers

Me (3:08 pm): no kids. Where would you like to meet?

Her: (3:23 pm): trying to think of a good meeting place away from downtown. Was thinking (expensive place) but kinda expensive... Any ideas

Me (3:33 pm): how about someplace in (nearby city)? (Named three possible place)

Her (3:34 pm): drive will suck

Her (3:38 pm): how about Mexican rest by kids house on (street name)? Margaritas & tacos?

Me (3:40 pm): (name of place) .. What time? You coming from sf?

Her (3:42 pm): no in (hometown) now. How about 4:30 pm?

Me (3:44 pm): sounds good. See you then.

Her (3:49 pm): perfect

Her (4:33 pm): in bar at table

Me (4:35 pm): In traffic going back to house to get mail.

Her (4:43pm) Ur killing me... U r never late to anything :-)

I showed up late because I needed to bring her mail to her ( which took me out of the way) and traffic was bad. We had a good time. Very laid back and casual. W touched me a few times and it felt slightly flirty to me. One of the things we talked about was friday night sailing races that i do with a friend. She sounded very interested in going and next possible race would be friday august 23. I told her she should come with me that friday. She said at one point in the conversation that she had given up on men implying that dating is not going well for her.. I am not sure how to take this comment.

Right after we left she text again

Her (7:39 pm) thank you for hanging out tonight.

Her (7:40 pm) next weekend sounds fun (referring to sailing races)

Me (7:51 pm) I had fun too. I'll try to get you on a boat

Was that a date or a just a friendly get together? We hadn't seen each other since May.

Skip forward to Friday August 16 (no contact between)

Me (1:40 pm): did you happen to pay any of (phone) bill?

Her (1:56 pm): Omg.. I got busy and forgot.

Saturday August 17

Me (10:46 am): ok. It is due today so I will pay.

Her (10:49 am): I will login and pay $xxx right now

Me (10:51 am): thnx

Her (11:07 am): just paid (phone) and (other cc bill)

Me (11:13 am): thanks

Monday August 19

Me (10:28 am) just FYI .. The (cc) bill is due by the 10th of the month... I am getting all kinds of reminders (for that bill).. I was late on my other cc bills this month too.. Bills suck

Her (10:34 am): I just paid $xxx

Her (10:35 am): I will check again at beginning of the month to make sure

Me (10:39 am): Reminder said (double what w paid) is due.. So I assume (other half) is due by sept 10th... Anyway hope you had a good weekend

Her (6:02 pm): got it. Will take care of it next pay check

Me (6:25 pm): you are the proud owner of another (bridge toll) violation which I would be happy to turn over to you over cocktails again sometime.

That brings us up to date. No response to my last text. My friend cannot do the race on the 23rd so I can't either (his boat). Should I ask her out to do something else? I am not sure if I have a window of opportunity here or not. I don't really know what last Wednesday was about. It felt very positive at the time and she seemed very interested in hanging out with me again soon. I just don't know how to begin the process of spending time with w again after all of this time apart. We had previously agreed to go to vegas until she canceled two days before. That is all documented here in this thread. Wednesday was my best day with her since we split up. We have met up other times, but they were not as positive. One difference in my actions for this time was that I agreed to meet right away. Previously I had been busy and we had to work to reschedule. Anyway, I am lost and don't know how to initiate spending time with w again. If we were just starting to date (without our history) it would be much easier. Any suggestions???

I might say something like...

"Hey... XXX won't be sailing Saturday. Since we had earmaked the time, we could catch a movie or lunch instead?"

Just a thought.

Kind of tricky... It seems like she is opening the door to peek out.

I would let her initiate any physical contact. A low key reactive response would be good.

I think that if I am going to reach out to her for this weekend I need to do it today. I have a lot of fear of rejection at this point. I do a lot of mind reading ... I get this sort of odd feeling that there is an OM that she would rather be with, but he is not giving her what she needs. She maybe even reaches out to me in attempt to make him jealous. I also kind of feel like I need to let things fall into place rather that trying to force things. Maybe the most attractive thing for me to do is to text her that the sailing thing is canceled and for her to enjoy her weekend. I could still tell her that I will be going out with friends (doing something else) and that she is welcome to join.

The sailing thing would have been ideal because it would have been exciting adrenaline rushing fun, but it would have been in a pressure free group setting. I think a dinner/movie date request may be too much right now. I just don't know.

The zoo is a good alternative... Exploratorium? Low key... fun stuff...

Thanks MrCAS. I was thinking about zip-line (which we have done before) or go-kart racing. My biggest issue isn't so much what we would do, but how to pursue her. I am worried about pushing her away. Even though she reached out to me, I feel like if I can't deliver exactly what we talked about then I am pursuing too much.

I think you are doing well to be cautious. Baby steps...

Gran Prix was always a favorite of mine when I lived out there.

Any women reading this? What would be the attractive thing to do here from a woman's perspective?

Right now I am leaning toward doing nothing and letting her reach out to me to ask if we are still on. It may be better if she thinks I don't care that much if we hang out or not. I am not sure if it is my fear of rejection that is guiding me or if that is really my best option. Maybe both.

Still seeking advice here.