I don't know how to handle this.(long post)

About 5yrs ago I met this girl on accident we had a class together in college and I accidentally hit her car and smashed out her taillight with my truck. We've been friends ever since. When I worked Saturday's by myself she would randomly show up at my work with either coffee or lunch, I never asked her to do this. I always offered to pay her back and she said no big deal. Whenever either one of us were dating someone we'd stay away from each other just so we wouldn't create conflict in our relationships. But when we're single we talk and hangout. I've been single for almost 7months and we would talk here there both when we were with someone because my ex and her were good friends(yeah I know some contradiction). But when I became single we stopped, until a couple months ago. I was up near where she lived and asked her if she wanted to meet up for drinks which she agreed (we live 2hrs away from each other). We start talking and she tells me how she thinks her bf might be cheating on her and she's not happy anymore. I give her the best advice I could without sounding like I wanted her for myself. She eventually breaks up with him 2 weeks later, and I offered her if she wanted to come down and hangout for the weekend she could, the weekend we set up she cancelled on the last minute and we rescheduled the following weekend because I invited her to an indy car race. She came down and I asked if she wanted to go for a ride on my motorcycle and she said yes. Later that night at dinner we were talking and she tells me how she's upset at my ex for moving on so quickly after she left me. Tells me how she absolutely hates her and if she sees her she'll rip her head off. She remembered things about me that I don't even remember telling her years earlier and like last week I started a new job and she asked me how my 1st day was. I wait to say she likes me because everything is pointing to this, I recently asked her if she wanted to come down in a couple weeks for another weekend and she said sure and we are currently planning on the weekend that works for both us. One night went for a ride in took a long way home and when I got home I had 10 txt and 2 phone calls asking if I made it home ok. I tend to over think things alot.

I would be cautious here, OP.

She is fresh out of relationship in which she suspected he was cheating. Generally, people in her position are still hurting and not really ready to date anyone seriously. You need to be careful that you're not setting yourself up to be her shoulder to cry on in bad times, only to have her move on to someone else when she's healed and ready to meet a new man - or return to the ex.

That's what I'm worried about and why I'm treading cautious. I don't think I'm her shoulder, because she does ask about me and regularly recalls stuff I've said from 3 or more years ago, and she does tease me and what not

So she still has a BF, and she thinks he's cheating? If this is the case, she's cheating also---emotionally. I'd be very careful, because whether she's ended this or will, you're going to be her fall guy. You'll help her move on and get over it and just make her ready for someone else. That isn't what you want.

He said she broke up with the cheating boyfriend already.

I agree, she may see you as a friend. Don't spend too much time doing friend like stuff if you really want to date her.

It's always hard to tell if one is reading all the signs accurately or being too optimistic, and if pursuing this type of thing would be wise in the long run. Can I ask, why are you interested in her now, and why have you never made a move with her before (like right at the beginning)? Is it possible you like the idea of her more than you would actually like her in that way? Are you considering it because other relationships haven't lucked out for either of you?

Make sure you are thinking about her benefit and your own benefit and that you're not simply doing this because of convenient timing. Always examine your motives and see what you've learned from past relationships. I would encourage you to keep being cautious and treat her with respect. A friend of that many years could be hard to start a relationship with, but you never know. Talk about it with her honestly when you get a chance, and when the time is right.

So reason I didn't make a move at the beginning was because she was with someone and she lived in the city I went school in. I went home for summer and she broke up with that guy after I already left for home, she dated another guy for a short time during that summer and broke up with him. We started hanging out right when I got back in town like it was that weekend. Same thing all over again she coming to see me at work on Saturday's for a lil bit then was hanging out with another guy and she blew him off to hangout with me. Again we drifted apart after she txt me one night asking me to come sleep with her when she was drunk, and I passed because I felt like it wasn't morally right. She ended getting pregnant by her best friend and they ended up dating for a bit and then they broke up and she started dating the guy she just broke up with. I did ask her out once before but I wasn't in the position i am now. I was broke barely had a job and lived with my parents. Now i live on my own, and have alot going for me.

So reason I didn't make a move at the beginning was because she was with someone and she lived in the city I went school in. I went home for summer and she broke up with that guy after I already left for home, she dated another guy for a short time during that summer and broke up with him. We started hanging out right when I got back in town like it was that weekend. Same thing all over again she coming to see me at work on Saturday's for a lil bit then was hanging out with another guy and she blew him off to hangout with me. Again we drifted apart after she txt me one night asking me to come sleep with her when she was drunk, and I passed because I felt like it wasn't morally right. She ended getting pregnant by her best friend and they ended up dating for a bit and then they broke up and she started dating the guy she just broke up with. I did ask her out once before but I wasn't in the position i am now. I was broke barely had a job and lived with my parents. Now i live on my own, and have alot going for me.

She sounds a little too eager and clingy. Is that your concern? Interesting she's running to you just after her bf cheated yet calling the kettle black here:

she's upset at my ex for moving on so quickly after she left me.

My ex broke up with me and was on to someone else after 2 weeks. This girl broke up with her bf about 2ish months ago and we started talking before but she was asking advice on how to fix her relationship then a week later they broke up and we've hung out for drinks twice while she was with him but she was asking advice the entire time. The 3rd time we hangout she told me her and ex broke up and 4th or 5th she stayed over at my house, drove down the 2hrs to hangout for the weekend. We didn't sleep together she slept on one of my couches. But we did go for a ride on my motorcycle and went to dinner.

So yesterday we talked alot. Pretty much texting all day. We talked about it years ago that I was thinking about moving to Alaska, and yesterday I brought up that I was going to go visit Alaska next summer for a week and just see some stuff. She asked if she could come and told me she'd love to live there, we both live in Michigan. So I said sure why not, she's really excited and is looking forward to next summer. We started talking about other stuff and she brought up why I don't see my friends that often and I explained that mostly because the competition with them is unfair when it comes to women and that they are all in relationships anyways so they don't want to hangout with the single guy. She said something like you guys meaning me and my friends and their gfs should come up and see her on Saturday and that she'll go with me to keep me company

Why would you discuss your local dating dilemmas wit her? It's unclear if you want to date her or just be friends with a friendzoning comment like this:

the competition with them is unfair when it comes to women

Why would you discuss your local dating dilemmas wit her? Is it that you are trying to tone her down and build some space and time? It's unclear if you want to date her or just be friends with a friendzoning comment like this:

the competition with them is unfair when it comes to women

So OP, why not just ask her on a proper date and make it clear that it's a date?

It seems you're both dancing around the subject.

I would tread carefully. I had a simple friendship many years ago. Started off as friends, I fell hard and for the most part we had a great relationship when he was single! He'd get a girlfriend and disappear for months. We'd meet up and it would be like nothing had changed, until he kissed me. Suddenly, I couldn't understand what was changing and for months everything just didn't feel right.

It sounds like you both need to sit down and be honest with how you both feel. She could just seek friendship after a breakup. You obviously have feelings for this girl, I would be coucious with moving into a relationship if neither of u r ready

We are past the friends stage, she sent me a topless pic the other morning. I didn't ask for and in the middle of the conversation she sent it and is like don't be weird. And then now we are actively talking about her riding me in txt

So you're edging into FWB territory?

If you want more from this girl, ask for it.

Yeah we'll see

We were talking and I admitted to her that I had been checking her when we hung out last and she kept pumping for answers because I was beating around the bush a bit so to speak and she saws something like grow some and tell me the truth, so I told her I like her which isnt a lie. She opened it and never replied so idk that means