When do you say "I love you"?

OlderAndWiser u
Her background: She is a healthy 63 year old woman who has been divorced for 8 years. She had one serious relationship after the divorce and it ended 4 years ago. She is an independent but traditional woman who wants a man for comfort and emotional security. She has one son who recently moved to begin graduate school. Also recently, she bought a house and is getting settled in.

My background: My marriage of four years ended about 9 months ago. It wasn't a bitter divorce but she finally realized that she did not want to be married. . . not to anyone. I live in an apartment and take care of myself fairly well. I have online dated for the past 9 months and had 7-8 first dates, one relationship that lasted about 6 weeks, and then I met her. I am self-employed and self-sufficient.

Our relationship: We have both worked in the same profession and have many friends and acquaintances in common. We both love live music and good food. We are both a bit quirky in the same way; I get her jokes when no one else does. I have spent much time helping her to get settled in and I have started painting the interior of her house. After dating for 2 months, we finally became intimate and we seem to be very compatible between the sheets. She seems to hold back emotionally more than me and I suspect that the previous boyfriend is responsible for her guardedness. Despite her reserve, she goes to sleep snuggled up to me with her head resting on my shoulder and my arm around her. She has met my family and gets along well with them. We have made plans for numerous events that we will attend over the next 4 months and she has invited me to travel with her to Italy next year.

She probably knows how I feel, but I have never told her "I love you." Should I tell her and hope that makes her feel more secure about me, or will it possibly scare her? I can wait. . . but should I?
When do you say "I love you"?
Add Opinion