As a precursor, let me just state that I stopped believing in "Prince Charming" a very long time ago. Nevertheless, I've had a crush on this particular guy since I was 14. Our families know each other well. His aunts and uncles live in my hometown. I was 14 and he was 16 when we first met. I was smitten by him immediately and he confessed me to (several years later when we were in college) that he had a crush on me too. When we were teenagers, he would come down to my hometown during the summer time to help out with his family's business.

He and I would flirt with each off and on throughout the years whenever we crossed paths (which wasn't too often unfortunately). To make the long story short, I am almost 33 and he will be 35 later this year. I live in the DC area and he lives in Chicago. We are both single. I think about him every once in a while. I am aware that I've built him up as some sort of "Prince Charming" inside my mind all these years. It didn't help that after a few failed relationships in my past, this Chicago guy became more and more appealing to me. Who knows...perhaps he is a real D-bag once I get to know him. I won't know unless I try, right?

So fast forward the tape to present day. My current project is ending and there is a new position within the firm that's opening up in a couple of months. The new position is in Chicago. I'm really sick of the DC area and looking for a change of scenery anyway....and, yes, I'm wondering if he and I can finally get our chance, after almost 20 years of flirting back and forth, to see if this is just a lustful/sexual thing or if there is something more behind it.

I realize that moving to a different city, for a guy who may not actually like me in a romantic sense, is a risk and something you may see in a Hollywood movie. However, I doubt that I'm the first person to do something like this for the possibility of finding true love.

SO, do you personally know someone that has taken the risk of packing up and moving to a different location for someone who may or may not be "the one"? If so, then did it work out? I know that, as a soon to be 33 year old, I sound like a fool. However, I really have nothing to lose. This new position isn't going to hinder my career growth and I do have some relatives living in the Chicago area already, so I will not be completely all alone in the city.

I want to hear if your opinion. Do you think I'm crazy or romantic? Believe it or not, I'm usually not the romantic type; rather, I've always been the "career woman" type of person. It's just that THIS guy struck a chord with me for the moment I saw him we were teenagers. I feel like I need to find out once and for all if there is something there or if it's just sexual chemistry and nothing beyond that.

just to clarify- i am a hopeless romantic. but a rational one (for the most part).

IMO- if the position makes sense for your career, and you do want to leave DC, why not? you do have some support there, it sounds like, and Chicago is a cool place. if you were going on a whim, just for him, and this thing with your job wasn't an option, i'd be telling you to reconsider. but it seems to be worth the chance. i don't think it's a matter of being crazy...i think its taking a chance, but making sure that its a risk that won't ruin your career or totally turn your life upside down. it seems to me like you have nothing to lose, and a possible fairytale to gain.

just a couple of questions- have you been to Chicago and if yes, do you like it/see yourself liking it? if you hate it, could you relocate within your firm back to DC or somewhere else?
also, if it doesn't work out with him, are you going to be ok with it, and will you be ok being in Chicago after that?

i only ask because i moved out to Seattle with my boyfriend in 2009, and he basically abandoned me here...(not trying to put a damper on things- your situation sounds wayyyy more promising than mine did...) and now i'm sorta stuck here. but i also came here under not the best circumstances career-wise. i think in your situation, it's worth a shot. i would.

It doesn't seem crazy to me at all, and you don't sound foolish in the least. It seems like a bunch of things are aligned in your life that make it a reasonable time to take a chance and see what happens.

I AM a romantic, but your story resonates with me for other reasons as well. I'm 32 as well and also live in the DC area. I LOVE Chicago, and it's really the one place I'd consider moving if the right job opportunity came along. If I weren't married and there was also a man in Chicago with whom I had the same history, and thought could possibly be "the one"? Yup - I'd take the plunge and see what happened. And I'm really not a person who typically takes many chances.

Sometimes we know in our heart that something is worth taking a chance on. If this is one of those times for you, I would grab it and see where it takes you.

Hi fllupthesky! Thanks for the quick reply back. In regard to your questions, here are my answers:

1. Yes, I have beeen to Chicago. However, it's been several years since I was last there and I was only there to visit my relatives. My visits would be only 1 to 1.5 weeks long, so I don't think it would be enough time for the "newness" of a city to wear off in order to get a sense of whether I liked it or not.

I have read a lot of message boards, such as Yelp, to find out what people think about Chicago. What I find very interesting is that people either love Chicago or hate it...there is no in between.

2. If I end up hating Chicago, then I can get a job transfer back to the DC area, but I would have to finish up my Chicago job commitment first. That would be 12 to 18 months of staying in Chicago. I can manage it.

3. If things do not work out with him, then I will be okay with it. It would definitely enable me to, once and for all after almost 20 years of fantasying about him, get closure or what not.

Due to my insecurities, I keep on reminding myself that him liking me back (after my weight gain especially) is a long stretch. I've read many relationship books take make one common message over and over again when it comes to men. That common statement is if a man is really interested in you, then he will muster up the courage and ask you out. So yeah...I'm hoping for something special, but I'm prepared for the "crash and burn". For all I know, he may be in a relationship right now.

4. I'll be okay in Chicago if he isn't interested in me. After all Chicago is a very big city, so I can "hide" from him and date other men.

Hi Chickadee! It's funny you mention things aligning in my life. I went to Georgetown last September to get my fortune read. A good friend of mine refered me to this particular lady who, my friend claims, predicted her future accurately. Last September, things were really bad in my personal life. Anyway, the fortune teller predicted wonderful things happening to me by the 2011 summer, that the stars will align, and that she does not see me in DC for much longer. Of course at the time I thought she was just full of crap and wanted my money....but if what she says comes true, then I'm heading back to Georgetown ever chance I get! LOL

When I read the thread title, my heart immediately said "YES!" Then my brain reminded my heart that my self is starting two new businesses that are very localized and that's not such a great idea.

But if that weren't the case, absolutely yes. I am admittedly a hopeless romantic and not one with a level head. I hope to be in love with the man that is in love with me one day. I guess my thoughts on limited story of you that I know are that while he's there and you are open to it, it doesn't seem that you're going there just for him. You're going there for a new opportunity professionally that will bleed into new opportunities personally. You might end up meeting your new best friend or another man that turns out to be the one. You might end up loving your new job even more or come across a different job or career path. I'm about to turn 33 and it don't think it's at all crazy to make a huge change. Even though I'm still in the same city, I've just changed my life dramatically and it's been amazingly fulfilling.

I guess if you really look into why you're going and you decide it's totally for him, the only thing you have to answer is if it doesn't work out, would you still make a go of it there? If the answer is no, then maybe it's not the right decision. If the answer is yes, then it seems to me you have nothing to lose! Good luck with your decision.

And just as an aside, I grew up in Chicagoland and have lived in DC. I LOVE Chicago and really didn't care for DC so that specific part of your situation has be going all sorts of heck yeah!

*EDIT* Looks like we were posting at the same time. Based on your responses to others, I think you've got it figured out. I'd take the leap and see where you land!

You've gotten some great advice here already, but I'll add my two cents.
Are you in regular contact with him now? You could always call him and tell him you are thinking about relocating to Chicago with your company and see how he acts about it. If he already is in a relationship, he may mention it. If he is not, you may be able to tell by the things he says if he is interested. You may be able to assess things without moving. Maybe it's time to be a little bolder than you have been with him? Go for it!

If what she said comes true, you have to promise you'll send me her information!!

sounds like you're all systems a-go! like you mentioned in your other post, i do think that sometimes the universe (stars aligning, however you'd like to look at it) gives us a "nudge" to do something and to follow a certain path. as long as you're ready, go for it.

also, i know we all get insecure, but go there with confidence in starting a new journey and chapter in your life. sounds like you were going through some difficult times recently, and you've pushed through, so pat yourself on the back for being strong and face this with strength and confidence. and you're on 3FC and on your way to a better you. and remember, confidence is always sexy

I left everything I knew and moved from Florida to Minnesota for Love and it was the best decision I ever made in my entire life. That was nearly 8 years ago.

I completely relocated at age 42 and it had nothing to do with love and reading over your list, I suspect your move doesn't really either. Sounds like you're just ready for a change so go for it.

If it was just for him, I'd say no, don't move. That would be crazy. But it sounds like it's the right time in your life to make such a move and he's just another factor on the "pro's" list tilting it big time in favor of you moving.

My aunt, at around age 45 I think, moved from Indiana to Holland for a guy!! She knew him through business. They're now happily married in Holland and she's learning Dutch.

I love your story. Makes me think I ought to contact the "one who got away" who only lives an hour from me. Hmmm....we're both single. LOL!

I agree. Sorry I would do absolutely nothing for love which doesn't even sound like what you and this man have for each other. Plus if there was an attraction between the two of you, these days staying in constant contact is so easy I would think the two of you would be doing that.
however you sound very grounded and it sounds like you should move for the job and once you get down there you never know who you will meet. So I say go for it!!!

I was in a long-distance relationship and we both decided to find a more central city to move to. I moved right away when a job came open that was a good career move, as I was ready for a change in my career. We broke up soon after that, before he moved. By that time, I was into my new city and new friends and activities ... so don't base it solely on him, but on YOU. Immerse yourself in the new surroundings if you choose to move. TONS to do in Chicago ... and if you find love with him, double bonus.

Good point by Carol - talk it over with him and see what shakes there. Go for the look-see visit and meet up with him and spend some time with him, so you know NOW and you don't get disappointed down the line and transfer that disappointment to the job or the city.

Good morning ladies! Thanks for everyone's input.

Hi DisgruntledOne! I love your post because you sound the "little voice" inside my head that tells me the exact same thing. I totally agree with you in regards to the fact that if there was an attraction between him and I, then one of us would have contacted each other. For example, in one of his emails to me a few years ago, he mentioned that he was in my hometown for a few days and thought about contacting but, but things got in the way. Of course the pessimist in me said "Yeah right! If you really liked me, then you would have made an effort to meet up for at least a 1 hour coffee date."

Then there was that time, in 2009, that I had a flight lay over for a few hours at O'hare airport. I was being a coward and just emailed him that I would be there for a few hours rather than calling him. It ended up that he didn't check his email until a week later and, in his email, he said he wished I had called him instead.

The latest communication between us was this past New Year's Day. I received a text message from him wishing me a Happy New Year. I didn't know it was him because I deleted his phone number in my cell (for fear that I would drunk dial him). Based off the area code, I thought he was my galpal and so I texted back to him something along the lines of "Hi Katie! Happy New Year to you too! I hope you and Neil are doing well." Needless to say, he texted me back in confussion and writing "This is Nick. Who is Katie?" Oops! I texted him back explaining my mix up and asking him how he was doing, but he never texted me back.

By the way, just to put it out there, I confess that I become a little ackward around him. It ranges from being a "shy school girl" type to thinking that I'm charming, but ending up sounding goofy. I feel like a 'Bridget Jones' type of woman whenever he is around me. It irks me that I react in such a manner around him, but I digress.

Yes, you may be completely correct. This may not be love at all. This may be just a sexual attraction and we just might end up having a fling and nothing more. Or it may not even progress to anything physical at all. He may just like flirting with me and that's all. Either way, at least I will no longer think "what if" in terms of him. I don't want to regret not taking a chance.