I work at a very large factory and I'm fairly introverted. About a year ago I got a new position that has me working all over the plant around a lot of different co workers.
One area had a woman that I was attracted to. Over time I started seeing her looking at me and turning away when I looked up. Then I noticed she seemed to get nervous a couple of times when I was closer to her to do my work, she would fumble and drop stuff. The next time I'm out there she's nowhere to be seen. I find out she's gone to the opposite shift and won't be back for 3 months. She eventually comes back about a month or so ago. I start saying hi, smiling to her and such. Last week I ended up out there like 3 days out of five instead of the one out of every week and a half like normal. Then one day I'm out there talking to one of her guy coworkers I'd gotten to know and she joins in on the conversation. A couple of hours later I'm walking past her and she stops me and starts a conversation with me. Next time I'm out she smiles and waves as I go by before I'd gotten to her area yet. Later when she sees me talking to coworker again she asks what we're talking about, I'd been telling him to check out a certain TV show I'm into. She loves it the show too. I tell her to check out a new YouTube vid, she says she will. I also find out a woman in my work area was her workout partner at the gym for a while. I ask my coworker if she's single and am told she was 6 months ago, she switched gyms and coworker hasn't had much contact since. At this point I'm really thinking things are going well and planning on asking her out next time I see her.
Then a couple of days later I get kind of blind sided. I get to her area. She's sees me, smiles really big and motions for me to come over to her. She says she watched it and talked about her and her boyfriend watching it. It took me completely off guard, but I think I hid it okay. I didn't say anything about him and just kept on talking about it. Then she tells me that a female friend the next area over got her watching and I need to go talk to her?
So, now I'm not really sure what's going on or what to do. What should I do?

You've got to stop the train of missed opportunities. I know you're shy and introverted, but if you don't ask her out on a date, you'll never get the chance to see if she'll say yes. If she's dating someone else, and you ask her out, she can tell you that she'd love to if she were single, or she can tell you that she'd love to -- period. From what you've written, it really sounds like she likes you, so the worst case scenario is that she turns you down because she's with someone else -- but you won't die from that. And... if she does end up breaking up with him (if it's even true she's seeing someone else), she'll have you on her mind and she may give you a clue that she's single again and interested in dating you. Bottom line, you have to bite the bullet, risk possible rejection knowing there's an up and a down side to this risk -- and that they're both part of life -- and ask her out on a date. You can even preface your asking her out by saying that you're normally shy but she's been too much of a temptation to stay shy -- and that you'd like to take her to dinner over the weekend. It's a way of flattering her, getting your point across, and putting the ball in her court. I can tell you're upset about the time lost when you haven't asked her and you're afraid of rejection, but I'm here to tell you to go for it. You'll feel much better having asked, and you never know what your answer will be until you do.

It's been a few days and only been around her once. I'm just hesitant because a couple of years ago something similar happened (not with anyone I worked with). Got to know a girl fairly well and felt she was into me. She had a recent BF, but was not happy with him. She flat out told me, so I told her if she wanted to I'd like to take her out. She kind of freaked out, wouldn't even give me a yes or no answer. From then on it was really awkward around her, we never talked a whole lot afterwards. She did end up leaving her boyfriend and started dating a new guy soon. I don't want that to happen with this current woman. It's not quite the same situation, I'm definitely a lot more comfortable talking with her. Since my last post, she seemed happy to see me again when I talked to her for a little bit. One question she asked seemed kind of odd to me, if I wanted to ever go to dayshift? I don't but most our coworkers do, she said she didn't either. I'm probably reading too much into it, but it seemed odd at the time. How's the best way to go about it without it ending up like the other girl?

I think gaining a perspective on dating will help. For instance, understanding that dating is a numbers game, is important. You're going to get a certain number of rejections in life, but you're also going to get a certain number of connections, and if you don't get up to bat, you'll never get a shot at either. You have to be able to face rejection and know it's not that big a deal. It means that someone you were interested in, or someone you like, isn't a match. It may be because she's taken, or she's not into you, or she's getting over a break up -- or any number of things. And guess what? This goes the other way, too. Women who will want to date you, may not win your affection. This is just life, and I would hate to see you miss out because you're more focused on fear than you are on winning.

I can't promise you that she'll like you or she'll want to date you, but I can promise you that if you don't ask her out, you won't have a shot at a date. From what you've written, she really seems interested, and I think you should ask her out and embrace life -- with it's ups and downs, wins and losses. Besides, women like confidence, and if they find you confident, they'll find you attractive. And.... this is a date. It's not cancer. It's not world war or world peace. So step back and see the big picture, loosen up a little so you're not putting so much pressure on yourself to win or lose, and give it a shot! Talk to her, and flirt. Tell her she's looks great and that you really like the way she does X, Y or Z. When you get a positive reaction, ask her if she'd like to have coffee or go to the movies over the weekend.

So, it's been a while since my last post. I never did ask her out. Every time I would mention something going on that I was thinking about going to or ask her what her plans were for the weekend to lead into asking her out, she would quickly bring up her boyfriend. I took it that she wasn't interested..at least right now.
A few weeks later I noticed she'd taken all of the pics of him off her Facebook. I assumed they'd broken up and I messaged her one Friday night. We talked for several hours, but towards the end she mentioned her boyfriend again. And not long after she told me they were getting an apartment together. At that point, I backed off a lot. I was still friendly to her but didn't see her as often and she seemed not as flirty.
I also ran into an hold friend I dated a little bit a long time ago at an outdoor concert in town and went out with her again a few times. But, I'm not feeling it with this girl and just want to be friends.
Well, tonight I saw the co worker again for the first time in a month or so. And made mention of a Facebook post she'd made last week about buying a lot to build a house. I told her I saw where you guys have bought a lot. She immediately corrected me that SHE had bought it, not them. I just said "oh". And she told me that things "aren't good". That they had broken up, but the lease is forcing them to stay together. She said he was just going to leave because his credit is bad, hers is good. But I guess they decided to stay together because she's worried about her credit when she's getting ready to build this house. The lease isn't up until September, but she made some comment about not knowing if she can make it till then. Should I have acted excited to her that they'd broken up? And is she sending me signals to ask her out? Do I need to let her know now that I'd like to take her out when she's single or should I wait until they're no longer living together?

There is only one thing in the world that is worse than rejection -- and that is regret. If you never ask her out, you'll always wonder and you'll regret that you didn't ever find out for sure. She's definitely interested in you, but believe it or not, she may think you're not interested in her. From her point of view you're the guy who's really nice, but never asks her out. Yes, she's got a complicated situation, but when she tells you that things aren't good with her boyfriend, and she wants to break up with him, she's giving you opportunities to move in and ask her out on a date.

How to do it? Acknowledge the situation, first. Tell her you know that this is awkward since her living situation is fraught with problems, but in spite of it, you'd like to take her to dinner or take her on a date. Put your cards on the table, and let her know what YOU want. If she tells you she'd love to go, then you've done something awesome for both of you. If she tells you she can't because of the situation she's in, tell her to let you know when she's ready. It may give her the incentive she needs to get out of a bad situation and into a good one with you! And if she gives you a blanket no, then you'll have asked and gotten rejected -- which isn't the worst thing in the world at all, and you'll be able to move on. But if you never ask.... you'll never have the chance to know where you stand, and she'll never have the chance to know, either. Ask her out!

Ok, I asked her to meet me for lunch. I thought that would be the best to feel out the situation with her (ex?)BF where we could talk away from work. Also, I've got an injury that's got me off work for at least 3 weeks and she's been taking classes part time before work. Here's how the conversation went:

M: (after I'd told her I was going to be off for a few days) Do you want to meet for lunch before work/class?
H: I would love to not have to wear work clothes all the time. I get dressed for work to go to class
M: I can do anytime, just thought that would be easier for you
H: Yeah, I will try and get up early on non school day
M: Ok, LMK when is good for you
H: I'll get back to you. and ended conversation with emoji of blushing smiley face.
Also, the next day I was rereading the conversation and accidentally liked one of her posts during that exchange with a smiling face with hearts for eyes, lol. I was just a comment of "oh, ouch" after I told her about my injury. Could that have freaked her out?
That's been 4 days ago and I haven't heard anything else, but since she said she'd get back with me I didn't want to come on too strong. Was the comment about work clothes a hint she wants to so something on the weekend? I'm thinking that comment and her ending with the blushing smiley face emoji are very good signs?

I'm so glad you invited her to have lunch -- but I think you have to come on stronger. You got a vague answer from her because your question was somewhat vague. So now, instead of letting her run the show, it's time for you to take charge. No more emojis and liking emojis -- instead tell her you got a reservation at a great restaurant -- hoping she'd say yes to dinner. And ask her if she'd like to have dinner with you on Friday at 7 at a specific place. In other words, make the reservation and ask her out on a date. If she says yes, you've got a date!! If she says no -- and it's because the particular date is not good, then ask her in that moment if the next Saturday night is better? In other words, pin her down for that date you want.

Because this "dance" has been going on for 8 months now, it's time let her know you want her! Women respond to that!! If she likes you, it'll be flattering for her to know that you want to date her so much, you've one out and made a reservation (or some other special date plans), and that you're the take charge guy when it comes to the relationship she could have with you. I know this is a little uncomfortable for you to ease into, but it's important. You don't want to waste your time with someone who's not into you, and by pressing forward, you're both flattering her if she's interested, and if she's not, you're forcing that response so you can let go and move on if that's the case. I hope it's not -- but I'd hate to see you waste a year on someone you haven't asked out because you're afraid of rejection -- and I'd also hate to see you waste a year on not asking someone out -- someone who wants to date you -- because of that fear. Carpe diem!! Seize the day. Get a reservation and ask her out on a date.