Dear Miss Emily:

A few years ago, I met a girl. We hit it off pretty well, but she soon started dating one of my friends. Over the course of their relationship, we also became friends and even though there was a little attraction, I kept it at the back of my mind. When they broke up, she was pretty torn up, so I decided she needed me more as a friend than anything else, especially acting as a buffer in our circle until things smoothed over between her and her ex/my friend. We spent a lot of time just talking about things and looking out for each other. She dated a few guys, since then, but there were times when she looked at me and I knew she wanted more, but because of our friendship and my own uncertainty I kept my distance. I used any avenue I could to convince myself that our lifestyles are too different:; she’s immature and irresponsible; I need to focus on my career; we both have had problems with depression and anxiety in the past, she’s religious and I’m not. The list went on and on. A few months ago, my mother died in a car accident. She was one of the first to call me, and insisted on coming over and talking with me almost all night until I could get on a plane to go home. When I got back after the funeral, she insisted on meeting up with me again to make sure I was doing ok. After all this, I realized that I can’t lie to myself about my feelings anymore. However, she’s dating someone else, again, and while I don’t know how serious it is, I know he’s one of the better guys she’s dated. It’s become very uncomfortable to be around her, especially when he’s there too. More importantly, it’s becoming a trigger for my anxiety, which I felt I had under control years ago. It’s causing me to avoid her, and even some of our friends because I’m afraid she’ll show up. I know I have to tell her, if I don’t I’ll drive myself insane. But at the same time I want her to be happy, and I don’t want to screw up what she has now if that is her chance at happiness. I don’t know how to tell her how I feel in a way that’s fair to her. Am I even right in telling her? I let the opportunity pass me by, why should she have to deal with it?  I just have no idea what to do.
Sleepless In . . .

-------------------------Miss Emily’s advice-------------------

Dear Sleepless:

What a horrible emotional roller coaster you have been on.  I am sorry to hear about the loss of your mother in such a tragic circumstance. No doubt you were forced to see, in the worst possible way, how life can be so very precarious and that seizing the moment has taken on urgent proportions. You have played the role of “nice guy” for quite a while it seems. (You might want to take a look at why that role suits you so well.)  But you were also smart enough to know that if you were with this woman, on a full-time basis, that there would be some incompatibility.  Not all of your reasons for maintaining a plutonic relationship are insurmountable but, nevertheless, immaturity, irresponsibility and religious differences are three potential red flags for a man who values maturity, responsibility and freedom of religion. Unfortunately, you have made this harder than it had to be.  Avoiding her and mutual friends is not what you should be doing, obviously.  It alienates you and your friends which exacerbates the problem.  Tell her you need to see her in private ( for drinks?) and gently lay the cards on the table.  You don’t have to make a fool of yourself – remain calm, cool and collected.  Tell her how much she means to you and what a wonderful friend she has been.  Say that you have had numerous regrets in not letting her know you wanted more than friendship but the time never seemed right.  Include the fact that you have no intention of disrupting her present relationship, but you felt it necessary to be honest and get feedback in order to pu this to rest.  If she has the same feelings for you, she’ll let you know.  If it’s only friendship she wants, you have given her the opportunity to be forthcoming.  And if friendship is all she wants, to save face you can tell her that your mother’s death might have been the catalyst to your heightened feelings of loss and your need to reach out.  This may be truer than you realize. But true or not, I think the death of your mother brought you to this crossroads in your life. I hope you choose the path that leads you to take chances and live life to its fullest.  Keep me posted.