Another thing I think you do need to do is really make sure this girl is worth it, because losing a friend of 30 years isn't going to be worth it just for somebody you have a 6 month fling with.
Don't look back at just the last little while when you have been romantically chatting with her (the potential of sex can cloud one's judgement).
Think of the whole time you have known her, and take into consideration some of the complaints that your buddy had with her during their relationship as well.
Also I'm not sure I would let the fact that she knows and understands what you've been through play into the equation either. It is likely that you are very comfortable with her because she would have already known what you have been through with your wife, making it much easier to open up to her about it, opposed to just somebody that you would have met off the street.
It's likely that there are plenty of women out there that will sympathize with you if you just feel comfortable enough with them to open up to them about it.
In the end it's your call, and if you think she is worth it and really want to do it then you shouldn't let a bunch of guys on a hockey forum tell you what to do. Just make sure you understand the risks of doing so, and are sure she is worth losing a friend.
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