The challenge of learning how to date a widowed man depends on a number of factors including, but not limited to, how long it has been since his wife passed away, how she died and what his mindset is at present. There are few things that you can do to decide on whether this would be the right time to attempt a relationship with him or not. Some widowers need more time to heal than others and you shouldn't take it personally if he is not ready to move on yet.
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Find out how long it's been since his wife died as this is a good indication of whether or not he is ready for a new relationship, or just in search of a replacement. In the article "Beware When Dating a Widower" on the Third Age website it quotes a woman named C.J. Turenne, as e-mailing, "I've been on the dating scene for three years and have found most men haven't healed from the loss of their partner, aren't ready for dating, and are trying to find the same lady as their partner."
Find out how his wife died because with long illness, though still tragic, it gives more of a chance to come to grips with her death. An example of how important this is when figuring out how to date a widowed man is in article "Endless Sorrow" in Psychology Today, which talks about the surviving spouses of the victims of Sept 11 this way, "The second year also brings greatly diminished social support. People are told to 'snap out of it' just as they are beginning to come to grips with loss. Widows and widowers are urged to resume dating before they can even bring themselves to remove a spouse's personal effects from their nightstand."
Ask him straight out why he feels he is ready to join the singles world again if everything else doesn't add up to a clear direction for you because if friends are pushing him into it or if he still cannot talk about his wife, it may be he needs more time to himself. You may find yourself in a relationship with him and the ghost of his departed wife forever if he doesn't take the time to heal.
Stay friends with him if you two have a lot in common and see what happens down the road. In the article, "Beware When Dating a Widower," that was quoted earlier, a widow named Judy Anderson says ""Dating will not heal wounds--time will. A widower needs family and friends if he is still in that place of hurt and depression."
Proceed with caution if you choose to get into a relationship with him too early, regardless of the warning signs that you've seen when learning how to date a widowed man. The article says it all by stating at the end, "Bottom line: Women should proceed with caution when becoming involved with a widower. If he hasn't healed, there likely will be trouble down the road."
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