Just a bit of info to share related to your post ... we have 31 members in the private "Widowed More Than Once" group here in Widowed Village. I recall there are a couple who have been widowed three times. Still standing. Surviving.
When Elaine died, I never knew pain that deep existed, as I'm sure that everyone on here can relate to. I realized that the reason it hurt so much is because our love was greater than the pain, and that gave me the courage to seek out a new relationship. I didn't think it would happen, because the dating pool at my age (58 at the time) was merely a puddle. However, I did find a wonderful lady and we got married.
I was very scared to set myself up for the potential to know the same pain again. I have climbed mountains, and know that climbers aren't fearless, they climb anyway. That is how I approached it, I had the fear, but married anyway.
If I were widowed again, I don't think I would remarry, not because it wouldn't be worth it, but because I couldn't suffer the pain a third time.
I am not remarried yet, but am in a relationship that will likely lead to marriage...that is our goal anyway, when the timing is right. I will say that it took me 3 1/2 years after my husband died to even consider dating, and a large part of the reason was that I was very afraid of taking that chance that I would have to go through losing a soulmate again, and I didn't think I could handle it. So, it looked easier just to avoid the chance by not being with anyone. But, then I realized how lonely my life was going to be, and how badly I missed and wanted those feelings of supreme connection with another person, so I thought I would give it a try. I luckily found my second soulmate right away (was the first guy I dated), and I am so much happier because of it. I can't imagine life without him in my life, and can't bear to think what a sorry existence I would be living if I chose to remain alone. That's not to say that I don't worry that I may lose him someday, and have to go through that unbearable pain all over again, but at this point, the rewards are so much greater than the worry. I just say a little prayer everyday that God takes me first, or both of us at same time, so I don't have to go it through again! LOL. Life is meant to be shared, and the last year and a half with my new man has given me a new lease on life, and I'm going to enjoy every minute of it!
My beautiful husband died over 5 years ago. We had been together for 37 years, ever since I was age 20. I was 57 when he died. The love was deep and I swore I could not open up to love only to go through such loss again. But as time went on, I could see that loneliness is a type of loss and slow death of me every day. I am currently (within the last month or so, in the beginning, stages of something magical of a man friend who I have known through the whole course of my marriage. He is divorced 10 years now. The friendship and respect have always been deep. Whatever we do, my deepest concern is for that friendship to go on forever. We are taking it a careful pace, but something precious is developing. And yet I still grieve my husband and love him. It takes a special man to get that. But after 5 years, the grief is not so intense, but the tears come even as I grow closer to this man. I still feel close to my husband's soul, but I think/know that he would not want me to be paralyzed in life through loneliness. I never thought this would happen, so I hadn't looked for it or even prepared for this moment. , I am much more alive now - I laugh and I started to exercise more. Before, I tried, but I barely cared. Anyway - it is worth loving again if the man has soul nobility in his heart.