Sorry for this lengthy post. I tend to ramble in full detail. Anyway: Have gradually met and become acquainted with this woman over the past year, as our daughters are in the same weekly ice skating lessons, and our boys play together running up and down the bleachers while the parents watch the skating. Over the past couple of months, I have slowly tried to build our acquaintance level, engaging her in brief conversation at the weekly skating lessons. We've talked about the boys (1 year apart), the girls (2 years apart), house buying, the kids' XMAS wishlists and what they wound up getting, a bit about our jobs, our homes, our pools, kids' school. Mostly small talk that you'd expect between parents who really don't know each other, but just having casual conversation. However, she has also elaborated on a bit more personal information in some of our conversations, about how her husband works nights, and she works until 2pm and then shuffles the kids to their activities, and 2 weeks ago, while talking about the kids and their schools, she mentioned that her daughter has a different father who is totally out of the picture. We chatted for most of the 40 minute lesson that night. So, anyway, that is a summary of the history of our acquaintance. NOW, I have really taken a liking to this woman over the past 2-3 months. Thru the power of the web, I found out her name, age, address and phone number, employer, and social networking sites. She has a peekyou.com account with a couple of photos, and she has a myspace account that is set to private. But what has really got my emotions and conscience going berzerk is her myspace profile page pic and her current mood state. It is a beautiful pic of her in her wedding dress, and the mood has been stuck on "lonely" for the past month since I found her myspace page. So, my emotions have me thinking that she may be in another unhappy relationship. NOW, I have decided to try to advance our acquaintance as cautiously as I can without stepping over boundaries and ruining what we have right now. After our pleasant and somewhat detailed conversation two weeks ago, I emailed her a short and unimposing message, just mentioning how I learned that her name is such and such, and how I didn't believe that we ever formally exchanged greetings during skating lessons, but that now I could put a name to a face. That was it. Of course, I was hoping that she would reply and start up a conversation. Well, she did not reply to that email. And last week, she was not at the skating lessons, likely due ot a big snow storm we had that day. Anyway, well, she was there tonight, though. Again, I didn't want to come on too strong and obvious, so I picked an opportunity when our playing boys brought us together, and I greeted her, and I proceeded to tell her how I came across her name, which was the result of an email to all the parents of the skaters, and I recognized her last name and place of business in her email address, and a google search on the oddly named company presented me with a business review on her company, and she was in a picture along with some other office staff. And she mentioned then that she got my email, and she wasn't 100% certain, but she thought it was from me. ANd we talked a bit more about her job responsibilities. My boy inconveniently took me away from the conversation, as he had to go to the bathroom. I got back to her with just a couple minutes left of the skating lessons. She asked me how old my son is again, and I briefly discussed our recent potty training success. Then, we were together again in the skating rink arcade after the lessons, as the kids got popcorn from the snack bar and, we both put quarters into the air hockey game for the boys. I finally wrapped up my kids and said "see ya next week". Now I have to wait another 7 days before I'll see her again. I will again monitor her myspace logins and watch to see if her mood status remains on lonely. She checks her myspace a couple of times per week. BUT I will not look to contact her (friendship request) on myspace because I think that will clearly demostrate my affection for her, and knowing that she is still in a marriage, and I really have no certainty regarding her marital relationship, if it is not going so well or what. I only have her myspace "lonely" mood status to go by, along with some of the bit more personal things that she has shared in conversations (a few of which I've mentioned here). I also most likely will not contact her via email again, as I don't want to be perceived as stepping across her boundaries and possibly turning off our budding acquaintance. I think my only sensible gameplan for now is to just maintain our friendly conversations at skating lessons and see where I can carefully steer the conversations without coming across as intrusive or boldly showing my strong affection for her. If I gain the insight that her marriage is okay, then I certainly wouldn't look to advance our relationship any more than what it is now. If I can manage to advance our friendship a bit more to email exchanges or myspace/facebook exchanges, then I could potentially call her out on her "lonely" mood status, and see what that reveals. I guess what I am looking for is some advice on how to advance our conversations and friendship level, with a certain level of respect for her and her life. What topics should I carry on with, and how can I carefully steer them in the direction that I want to go, to the point where I'm going to possibly gain the insight that will tell me to continue my desire to advance her or to back off. I've researched flirting techniques, but I obviously want to be as subtle as I can. Any advice? Thank you very much.