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Navigating Love & Loss: Should You Propose After a Breakup?


Question
I'm in my 50s & met this women online thru a dating service. We emailed for months, met personally, chemistry was there and we had a great committed dating relationship which involved making love together for almost 2 years. We both are divorced following over 20 year marriages and came together. We have so many things in common, think a like and came to know each other very well. During the time that we dated, I did not tell her that I loved her, because I did not know and was scared to say so. I told her that I think actions speak louder than words & I showed that I loved her. After we had several misunderstandings &/or arguments, she broke up with me in October saying that "it was not working for her". I asked what that meant and she said that she needed a break from dating me and asked for her things back from my house.

I realized after we broke up that I do love her very much. We have continued to stay in touch & see each other as friends. We have so much in common that it would be a tragedy not to at least be friends. I have told her on several occasions that I love her. Once when I told her she said sometimes timing is everything. She has told me that she does not think it is "rocket science" to have known if you love someone after having been in a committed, intimate dating relationship for nearly two years. All that she has told me may be right...but at the time I would not lie to her. I had very strong feelings for her...and still do...but did not know if it was being in love. Since we broke up, I have told her that knowing if I love her should not have to happen on a timetable. I know that what we had for nearly two years was very good and I was very happy. I was going with the flow so-to-speak. To cut the the chase...I now know that I love her very much...am thinking of asking her to marry me because I think timing could be right...and she has shown signs that she did love me. We have been seeing each other, as friends every weekend recently...have talked about the fact that remaining friends allows for the relationship being more. However, she still mentions that we are "just friends". Sometimes when we are together I sense she really wants to date me again. Other times, I have no clue. She has told me that even though she likes me very much...and cares for me...she apparently does not love me. I am thinking of just coming out and asking her to marry me. I do not have an engagment ring...but think we could get that together if she wants to marry me. When she and I were dating, I did not know where the relationship was going and did not even know if I wanted to get married again. She knew she wanted to get married again. We discussed those things. Now...she says she is not sure if she wants to get married again. She is not sure anymore what love is. I know she wants to get married again because of the dating relationship which we had. I know her well. I think she did love me...but after the breakup something happened with her. We both have gone out with other people and found that what we had/have together is better than anything that we found out there. So we still talk, email and see each other.

I do love her and want her to be with me for the rest of my life...but am not sure if now is the right time to do it. Please give me your thoughts on my situation. I'm thinking of taking her to dinner and telling her that I love her so much that I would like to marry her in lets say one year or so. Thanks....

Answer
Hi Mike - thanks for writing.

This is a classic case of "less is more".  If you come on too strong, you are probably going to push her away.

Your strategy needs to be to create a place for her in you that is warm, loving, accepting, and open.

In other words, you are going to have to be completely selfless to get this done.  Within reason, whatever she wants - do it.

If you know she likes a particular flower - bring one to her for no particular reason.

Without overdoing it, send her a little note saying you miss her.

In short - you will have to do some serious courting of this relationship in order for her to become convinced that being with you is the happiest place on earth for her.

I do not think that asking her to marry you will be effective right now.  Be patient.

Court her.  Create in you the most positive place she could be - because you think of her first and yourself second.  Most women find that to be irresistible.

Give that a try and let me know how it goes.  We may need to adjust the approach depending on her response.

David