Am I going down a road that says "Dead End?"

A little background on myself. 32, single male, airline pilot, got out of a 5 year relationship earlier this year. June 20, I ran into a random girl in the airport. I never approach people in the airport when I'm working. But I noticed she was charging her phone, and I engaged in conversation with her. She was 28, from Ohio. I live in Chicago, but am from Detroit. We talked, and I said goodbye. Before I boarded a plane to Detroit to see my family, I turned around and gave her my #. I got a text from her when I landed. We've texted almost daily since then, talk every other night. The day after I met her, I called her and asked if she wanted to do dinner. She was kind of shocked, but agreed and I flew down, had dinner, stayed in a hotel, and went home the next day. Since then, I've been down to her place 2 other times. She is a very independent woman. She has told me she has her walls up, and that she was married for 2 years, and found out her husband at the time was having a long going affair with another woman. She now lives alone, and seems to be very cautious with proceeding forward. It's been a month since I met her. In that time, like I mentioned, I've gone down there 3 times, sent her flowers to her work, and have told her I have feelings for her, and want to know where this is going. I get provocative pictures from time to time from her which I have no problem with. Even simple pictures like her laying in bed saying "Your favorite place." We have not done the deed, only messed around. But sometimes I feel like I am getting contradicting messages from her.

Her email response was " I just don't like to say anything or share anything until I'm 100% sure about it because I'm afraid if I do say yeah I want it to be us and things like that then it doesn't work out or feelings change you feel like I was misleading or hurtful or I don't know something like that. I also know that you need some guidance to on where things are going...this is the best that I can do at the moment:I like you, I like spending time with you, I don't ever spend time with someone (more than one date) if I don't see potential for more...more being what I'm sure you are asking. I want the same things that most people want..someone to share their life with etc. I am just not 100% on my feelings yet so I just didn't want to say something or do something that might make you think one way if I wasn't behind it 100%. I don't know if this makes sense at all and we can talk later about it. I just haven't loved or cared about anyone in years and maybe I'm not real sure how to anymore but it just takes me a little longer to get there. "

It just seems like I am putting all this verbal, emotional, and physical effort in, but not really seeing it back. Last week I told her when I was off this week, and she told me tomorrow (Thursday) would be the best day to come down for a dinner date. I told her "you let me know!" I am thinking if I don't hear anything by tomorrow morning, when I finish work, I will just go home. NO reason to bring it up or pressure anymore to see her, I put my cards on the table.

Am I going down a dead end road here? Any input would be appreciated.

The pics she sends are a direct contradiction to everything else she's said and done. That's a red flag, in my opinion, and I think you should simply ask her what she means by it.

Good point you bring up. My question is, what is the best way to bring this up, and should it be in an email/phone/text or next time I see her face to face? I was thinking next time I see her face to face. Seems like every so often I get a topless shot of her, or in a bikini, etc. Nothing too hard core, and don't mean to get to graphic.....but when I see stuff like that, my thinking is a normal person who is not interested in someone who never send stuff like that. She has told me in email that " I have feelings..but I know I'm still a little closed off from being hurt ( and I'm talking like physically hurting..pain that literally hurt my heart..can't even begin to describe) I'm better but not fixed and I never ever want to hurt anyone..or make someone sad just want to make them smile.

I don't know what will happen...I don't..have to find out I guess. U won't mess them up and I'm not concerned about the distance u just adjust and down the road make changes..

I'm just trying to be happy and do what makes me happy..I need it..more than u know.."

So I just don't know what to think anymore.

In my opinion:
This woman is completely in love with you. She is just afraid of getting hurt, nobody would send pics like that unless if she was a whore, but u've been with her enough time to see this is not the case.
You have feelings for her, and she was nothing but trustful to you. She is telling you the truth. She meant by not being 100% sure is that she is 99%:P she is just afraid of getting hurt.
If i were you i woudndt give up on her. A woman when she is hurt, she kinds of block herself from getting hurt again, and you and the sweet things you have been doing are read as threat to her, a kind of temptation that can lead to suffering again. She needs to feel safe. Make her feel safe, loved and show her you have no dead line for your love.
When she feels safe around you, she will open up her heart and then you can get every effort you've put in this relationship back.
This is for sure not a dead end road. She does love you. And the problem is for her ex being such a piece of shit, nice people like you have to go throught this now. But i am sure she will surprise you soon
Good luck with everything:)
Dont give up on her

Well she called me before bed tonight. We talked a little. Nothing was mentioned about the suggested dinner date tomorrow. So it is what it is, I'm not going to keep bringing it up. It is a tough situation, seeing how we text each other a lot throughout the day. I don't know what tomorrow will bring. I know I will be a little disappointed that plans were never finalized when I told her to let me know. But again, it is what it is. I may not be in too much of a hurry tomorrow to respond to txt's due to that fact alone. But I will continue to take it slow. Just complicated.

If she was in love with me (too early for that, but at least had a deep interest at least) I don't understand why I am pulling strings to see her when I have time off and getting little of that in return from her. I gave her 3 options on a dinner date, this past Monday, tomorrow night, and next Monday. She told me again that tomorrow would probably work out the best. If she did feel like what you say, then why did she never bring it up to finalize it? Who knows.

Maybe she's getting some bad advice from a friend about how to keep your interest while she strings you along. That might explain the topless shots. I must admit, I find that a little shocking. I don't really have body shame issues, I've been on plenty of nude beaches, etc, but I would NEVER send a man a topless picture of myself. It just seems slutty. It's really weird, considering how cautious she is otherwise.

If you get to see her tonight, I hope you explain the concept of mixed messages to her. It's like she's giving you a green light and a red light at the same time.

sorry this doesn't sound too good to me. the first few months should be blissful not confusing. remember when someone is genuine with you, confusion is not a part of the equation. i suspect there is a little something else going on like maybe she is seeing someone else, or maybe she is not over her ex yet.

you should be turned off at the pics. why is this ok with you knowing she is nowhere near ready to commit to you? perhaps she sends them to all her first dates.....what a classy girl!

Great advice.

I did not see her tonight. She informed me after I asked about why the date did not happen, that she has been moody / bitchy all week, and didn't think her company would be any good given her state. I then told her I didn't mind, and she said she didn't know I wanted to see her that bad. I've made it evident, but oh well. I want to bring up the pictures / lack of a commitment to her. I truly feel it should be something I bring up in person, opposed to phone/text/email. Would you agree? If that is the case, next weekend is a tentative date with her. I kind of what to email her the concerns, as she has told me if something is bothering me, to tell her. But I am not sure if the point would hit home with an email or phone call.

well you said it right there with "tenative" date. assume it's not going to happen, be grateful if it does. when i like a guy there are very very few tentatives, i will find time and make it work, if not one day then the next. this moody/bitchy thing is not a good sign either. she is avoiding you.....why? remember dating is finding out if someone is compatible with you.

here's another angle......tell her on the phone that you agree about going slow and it takes time to get to know someone. however you only proceed if you know the person is interested.....tell her the pics and the"tentatives and bad moods" are diametrically opposed. but i doubt you wil get a direct honest response. often times people with confusing behavior don't know their own minds or they are manipulators.