Samara O'Shea

Would You Give a Guy Who Broke Your Heart Another Chance?

Hi Samara,

I am 42 years old. Divorced twice, no children, 1 dog. Recently, I reconnected with my high school sweetheart. He is divorced with 2 children. We are madly in love once again and I think I want to spend the rest of my life with him.

The problem is that we reconnected once before in our late twenties and it didn’t work out and I was terribly hurt by him. I see many positive changes in him since we started seeing each other again. This is the third time around with him. I am wondering if we both needed to grow up before finding each other again or am I just fooling myself?

Any suggestions on how to approach this relationship this time around. I really want it to work.

Thank you,
Merilyn

Check out my response here.