Assalaamu alaikum Farhan,
(smile) I think it is a beautiful thing that you care about this woman. If more Muslim men thought about looking after women the way you are contemplating… we would have stronger families, and a better Ummah, I believe.
I know a couple rather like what you are describing. They have had some ups and downs, but things seem to be working out for them. (smile) They are expecting their third child now.
You'll have to tell your parents sooner or later. I would suggest, though, that you do a little homework, first. You need to realize that you are likely to confront some difficult situations, and prepare yourself for them. If you are prepared, you will also be able to discuss the problems with your parents in a way that may help them to realize that you are ready for the challenges.
Men can be strangely possessive at times. They may not want a woman anymore… but they may also not want anyone else to marry them. You may therefore have to deal with her unpleasant ex. Her children are likely to be a source of continuing grief for her, and for you. If the ex is abusive towards them, if he poisons them against her, if they are in any sort of trouble (and children from broken and abusive homes are more likely to have problems with the authorities, gangs, drugs…)… she, and you, are likely to feel pain. If you have contact with these children, it will be hard for you to be respected by them. And as you are young, with perhaps little experience in dealing with children, it will be hard for you to know how to handle them.
You might want to look into the woman's family. What sort of relationship has she had with her parents? Any siblings? Other family members? I'm not saying that you should condemn her if there are any problems there; but be aware that our first love relationships with our families have lasting impacts on our future relationships. If you can understand the family dynamics, you can make informed choices, and perhaps find ways to deal with whatever issues there may be.
How to do your homework? There are various books about blending families, dealing with children, family relationships, legal recourses… (smile) you name the problem, there is likely to be a book about it. Look around. You could also talk with her family members (preferably with a mature person with you to help you), and try to get a feel of the dynamics. Take your time. People may put up a good front at first… but if they are false, this shows over time. Are there any patterns of behaviour that may be problematic? Are there steps you or she can take to mitigate them?
If possible, you could also look into the ex. What is known about him? His family? How could he impact your life? What could you do to minimise possible negative impacts?
The children are with him. Why? Does she have any access to them? Might they live with you on a part-time basis?
You could also look into the possible positive aspects of this woman. She is obviously capable of having children (unless she's taken steps otherwise… have you talked about children?). She has, presumably, some experience with dealing with children and running a household. Does she feel grateful towards you? Does she respect you? Would she be happy with less than some other women might? She has had her faith tested… is it strong?
You say she is hesitant to marry again. That she is afraid to trust. Would she be willing to work on these before you marry? Would she be willing to go for counselling? Is she able to see what mistakes she made during her marriage (we all make mistakes)? Is she willing to take responsibility for her life, and make some changes?
(smile) There are a lot of questions. But if you want a successful marriage, and if you want to show your parents that you are ready to take on these challenges, these are all things to consider.
(smile) And of course, after you have done all your homework, there is the istikharah prayer (
http://www.islamicity.com/articles/A...ef=MM1201-4985).
May Allah, the Distressor and the Source of Good, Bless you for your good intentions, and may He Smooth your way if this is good for you in this life and the Next, and Turn you from it, if it is not.