Dating a widower over 50 or 60 is never easy. They have baggage. Plain and simple. But dating a widower can also be a wonderful thing. When the widower is over 50, the have so much more life experiences to share and love to give. If you can get over some bumps in the road and give them the kind of love they need, it can be a beautiful blossoming romance. He's in his prime, and he's ready to find love again.
He doesn't want someone to replace his late wife. He loved her and lost her. This wasn't a break up. He isn't looking for someone to take over the same role as his wife. He's looking for a new relationship. A new woman to date and have a relationship with. Whether he lost her one year ago or ten. It wasn't a choice, and chances are he doesn't want a clone of his wife. He wants to find love and companionship with a new woman. Be that woman, not the woman to fill in the position.
There is a good chance there are grown children involved when you're dating a widower over 60. Maybe they are encouraging their dad to get out there, or maybe they are not ready for him to date, but one thing is certain. You are not going to be their mother. These kids are grown, quite possibly with families of their own. It's great to have a relationship with them, but do so on their terms.
His children have been raised by their mother and even though they lost her, they do not need a new one. Give them space, and let them decide how to go about the relationship. Let them set their own boundaries and set the pace. Maybe they will want their kids to call you grandma, maybe they won't want you to meet their kids at all. Let them decide. This also goes for other family. He may have siblings, parents, even in-laws. Be respectful of these relationships and let them decide what kind of relationship they want to have with you.
Dating a widower over 50 is a different experience than a widower in his 30s or 40s. He has grown into the man he is today with a woman who was his wife, and he may or may not want to marry again. I think this is where you really need to leave it up to him. Don't pressure him with questions about when and if he wants to remarry. This may scare him away. He lost his wife, and now wants someone to love, and have fun with.
Don't bog down the relationship with engagement or marriage talk. Who knows if that's even on his radar. If marriage is something you really want, it's okay to bring it up, but keep it light. You can ask him his thoughts on it, and let him know yours without asking when he's buying a ring. Let your feeling be known without making it awkward. He's looking for a companion to go out and have fun, what that blossoms into, you never know, but don't make the whole relationship about whether or not there's a rock in your future.
As mentioned before, this was not a break up. He did not choose to lose his wife. They were still very much in love when he lost her. That love will always be their. You cannot expect him to just let go of his feelings for his late wife just because he's entered into another relationship. You cannot let jealousy get the best of you.
Don't make him feel like he can't talk about his wife around you. He will want to share that part of his life. Let him. Be that person in his life he can share his joys and sorrows with. If he doesn't feel comfortable sharing these feeling with you, your relationship will suffer. Don't make him feel guilty for still loving his wife. He can love both of you at the same time.
Dating should be fun. It's an exciting time when you're getting to know a new person. Just because their are some heavy feeling behind the relationship, don't let them drag everything down. Go on a date to see a play. Go to a bar to have drinks. Don't be boring. Do fun and exciting things together. He's in his prime. Don't let it go to waste. Go on adventures to see the world. Whatever it is you do together, just have fun.
It's been said, widowers over 50 have baggage, but they also have so much to give. Be the woman he met and wanted to get to know, give his family space and let them come to you, don't start throwing around marriage talk, let him love her and you, and have fun. This is the key to a new and exciting relationship with a widower over 50 in his prime.