DKT writes in: I met a man on Match.com. We are in our 50’s. He divorced his first wife after 20 years of marriage. He was married to his second wife for about 5 years before she was killed in a car accident in January 2009, just 9 months ago. We have been on several dates. After we spent a day together at an event, we went to his house. Her shoes were still by the dresser and her lipstick was still on the cabinet in the bathroom. There are photos of her on the refrigerator. We kissed, but that is it. I slept on the couch. I live over an hour from his house and it was late. Is this man ready for a relationship? It is my feeling that he is not. I really like him and could see a long term relationship. How do I proceed with this relationship? If we continue seeing each other, will he see me as a replacement for her? Do we see each other once a month? More? If he considers me a friend, what are the odds that the relationship will ever be more than that? My mothering instinct is kicking in and I want to help him through this grief. Am I setting myself up for heartbreak?

Allison Daily, co-author of Out of the Canyon, responds:

Dear DKT,

I think the questions you ask are important ones. I want to say first that I think the key to this is: you really like the man and could see yourself wanting to explore the relationship further. I have no idea if he is ready or not, but the shoes and lipstick aren’t a very good sign. I would take those as a warning sign in protecting yourself. Your mothering instinct, while wonderful, is not appropriate in this situation. He doesn’t need a mother, he needs a counselor, therapist or support group. Sometimes men resist those and like to do it on their own. In any case, it is not your or my role to judge that. My suggestion would be to explain to him your feelings about your attraction and also the concerns you have. You can let him know that you’d love to see him at a later date after he has worked through his grief/pain, etc. If he asks, you can suggest some support possibilities. This isn’t easy because you do like him and are obviously attracted to him. I just think you have a better opportunity of a relationship in the future if he can work through the relationship he lost more completely. He’ll have more to bring to the relationship with you.