Here are two very throrough articles on things to ask before marrying again. I'd say consider these questions before you even date, and especially read the comments on the first link to guard yourself against additional grief others have experienced.
You'll see why it's wise to let yourself heal before entering into a relationship again.
1). For Widows and Widowers Who Are Considering Remarriage
This next article provides a lenthy list of questions that might be used for pre-marital counselling sessions. Don't let it scare you off, but rather keep these questions in mind when you start dating. They'll help you discern where the relationship will go and can save you from problems in the future. However, DO NOT take these on your first date and turn it into a interrogation! Just keep them in mind before things get serious.
2). Questions To Ask When Preparing for Marriage
♥ ferree
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