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Dating too soon can cloud your judgment while delaying too long can render you undatable. How long should I wait before thinking about dating again. First thoughts are why wait and to just get out there, sign up for OLD and start having some fun. I'd be really interested to hear what others have done. Personally I would wait a bit, get. Your head together and get used to your new situation for a while. If you are contemplating online dating, it is not for the faint hearted. There is always a danger when you have been hurt and starved. Of affection that you will jump feet first into a relationship with the first man that shows you attention.